The Come Up

Aaron Levant is the CEO of NTWRK. He's one of the most exciting builders at the intersection of fashion, culture, events, and media. We discuss launching a profitable car magazine at age 9, pitching Marc Ecko on ComplexCon, raising tens of millions for NTWRK from star investors like Jimmy Iovine and LeBron, being "oppositionally defiant", and how he thinks about his career in thirds.

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EPISODE TRANSCRIPT:

Chris Erwin:

Hi, I'm Chris Erwin. Welcome to The Come Up. A podast that interviews entrerepreneurs and leaders.

Aaron Levant:

This is a common theme in my career, which some people say ignorance is bliss, I like to say ignorance is rich. What I mean by that is it's like every single thing I've done I don't know anything about. And when you know too much about something, you become institutionalized with fear. It's because I knew nothing about putting on an event or a trade show, I wasn't scared of it. I just did it, and didn't think about it that much. It just happened, and it was luckily successful.

Chris Erwin:

This week's episode features Aaron Levant, the CEO and founder of NTWRK. Aaron is one of the most exciting builders at the intersection of fashion, culture, events, and media, and he started super early. At just nine years old, Aaron used picture cutouts and a Xerox machine to launch a car mag, and it was profitable. He sold copies to friends at school and advertising to neighbors. Then in his early 20s, Aaron launched a fashion trade show, which he sold to a major exhibition company. There, Aaron had mastered the biggest experiential businesses of the past decade, like when he pitched Marc Ecko on ComplexCon. 

But Aaron's not just a builder, he's also operationally defiant. He doesn't follow norms and believes that lack of experience is major advantage in launching startups. This mindset fuels Aaron's current business, NTWRK, which powers shopping at the speed of culture. NTWRK is hands down one of the hottest players in content and e-commerce and has attracted backers like Jimmy Iovine, LeBron, Drake, Foot Locker and many more. 

Now, Aaron's story is remarkable but his character is more impressive. He's unconventional, uplifting, and so grounded. That plus hearing him talk about his future plans for NTWRK and how he thinks about his career in thirds makes for a must-listen. 

All right, let's get into it.

Chris Erwin:

Tell me a little bit about growing up in the valley, your household, and what your parents were like.

Aaron Levant:

Valley here in San Fernando Valley in LA is a nice place to grow up. A little bit of suburbia, very, very close to LA. My parents were amazing people who were very creatively inclined. My dad was in the entertainment business and spent a long time as a writer, television shows, and things like that. So I'd say I grew up in a pretty creative household. My mom actually had a little independent clothing label in the '80s, so I had some adjacency to the apparel business that I properly didn't even realize until years later, but my mom was always involved in that. My parents were very into pop art, into pop culture. My dad's a huge toy collector, he has 50,000 toys. So this affinity for pop culture is something I've been growing up around my whole life.

Chris Erwin:

Between your father's toy collection and then also being a writer in the entertainment and your mother in commerce, the whole new shoppable entertainment, starting to get where it comes from pretty early for you. When you were growing up, did you think, "oh, yeah, I want to go into Hollywood. I want to be like my dad or I want to do what my mom does." Was that going through your mind at all?

Aaron Levant:

No, never. I mean, I had no interest in doing anything my dad did. I would say, like most people, probably I wanted to do the opposite of what they did so I never ended... Even though maybe what I'm doing has some connection to the entertainment industry now, I was always going the other way. I would say... I never met him, but my mom's father, my maternal grandfather who I never met, was very entrepreneurial. I felt like I've always had something ingrained in me to be entrepreneurial, which different than what my dad did and being interested in businesses where my dad has no interest in business whatsoever. He almost despises it to a certain extent. So I would say I rebelled against anything my parents did and wanted to do my own thing, for whatever reason.

Chris Erwin:

What type of businesses was your grandfather building back in the day?

Aaron Levant:

He was in real estate, which is something I didn't get involved in either. Again, I hear this all by way of my mom and my grandmother, but he was just very entrepreneurial from a young age, always trying stuff, apparently a very, very smart guy. So, I try to think that's where I get some of smarts from, because my dad is just not a business inclined guy. He's all about being creative.

Chris Erwin:

I think you need both sides of the brain for what you're building right now, so it makes sense.

Aaron Levant:

Definitely.

Chris Erwin:

Your entrepreneurial ambitions, my understanding is that they manifested pretty early. I think you put together a car magazine at eight or nine years old, right? And then you were selling that to some of your school friends?

Aaron Levant:

I still am and was back then interested in cars. Sometime around maybe nine or 10 years old, I had made a car magazine through just, I guess what now be a zine, just cutting up a bunch of other great images of cars from books and going to Kinkos or what was Kinkos now FedEx now, and photocopying it. I went to my next door neighbor who was an Arby's franchisee, and I sold him the back cover advertisement for I don't even remember the price. But I just knew that my magazine wasn't going to be legit unless there was an ad on the back cover. So I guess I tout that as my very first business deal, and then I was selling that magazine at school and at camp. For whatever reason, I just felt like I was always trying to do stuff like that and did various random projects as early on as that all the way till I was 16 when I started doing some form of real business, I guess.

Chris Erwin:

So it felt like in your pretty early on was that you just wanted to do stuff. You wanted to create, you wanted to try things out. There's just this hustler inside, right?

Aaron Levant:

Yeah. I'm not even sure where it came, but it just felt natural to me to try to create and try to monetize out those creations.

Chris Erwin:

I've also heard you describe yourself as you go through your teens years as being, and I think that's persist through today, oppositionally defiant. Is that right?

Aaron Levant:

Yeah, I think that's an actual word from the DSM, which I think is the book that they use in psychology to define what's wrong with you. It's like the dictionary of mental illnesses. I think my mom pointed that out to me very early, which is I had a tendency to go against authority, for good or bad reason, whether that's kicking the principal in the leg at the first of preschool or doing any number of antics I did through my elementary and short high school years. I always felt the need to go the other direction and go against the grain, against authority. And that was, for some reason, instilled in me, and I think a lot of it had to do with the fact I just wasn't interested in being in school or be at camp or being anywhere there was authority figures trying to tell you what to do and how to dictate what you do with your time. It was all very boring and mundane for me.

Chris Erwin:

Through that resistance earlier on, did that also attract these types of friends and people that you wanted around you? Were you becoming a leader amongst the peer groups saying, "I'm going to do things differently." And people were like, "Yeah, we're going to follow Aaron?"

Aaron Levant:

I would say, as you know, depends. As I was younger, no, I think most of the kids I was hanging out with were pretty nice and I was the jerk in the group. As I got older, I probably attracted the wrong people, and then I spun out of that when I was 18 years old. But no, I was just always doing wrong for myself, not necessarily with others or for others.

Chris Erwin:

My understanding is that in 10th grade you get out of high school and then you start interning at GAT. Tell us what was GAT, and why was that interesting to you at the time?

Aaron Levant:

Probably one of the second or third business adventures was I was really passionate about design and graffiti art and street art all through the '90s when I was a young teen. And being interested in that design and graffiti art and being interested in business, I was trying to figure out how do you make a living out of doing you're passionate about. And then it dawned on me that all graffiti writers were working at GAT, particularly the main place and many other street wear companies doing the T-shirt designs. If you're a great graffiti artist, you're doing topography, it's a great transition into designing t-shirts and make a living for yourselves, so I said, "Okay." I started to develop an affinity to these companies.

Aaron Levant:

Randomly, a guy I grew up with, Tal Cooperman, introduced me to the owner of that company. Through meeting him a few times, he ended up offering me an internship, and GAT was the definitive late '80s, mid-90s street wear brand in LA. It was such a great opportunity for me not only get close to this company and learn a trade that I was interested in but also be around some of my favorite artists and learn from them and learn a craft which at the time was graphic design for me in the beginning of my career.

Chris Erwin:

Going back to that moment, were you like, "Yeah, this is the logical progression for how I get into my career."? Or were you a little bit shocked as, "Oh, I wasn't expecting to go down this path, but... "?

Aaron Levant:

I don't know if I was thinking in terms of it as a career, I was just so excited. I was such a fan, right?

Chris Erwin:

Yeah.

Aaron Levant:

I forget the days when I was legitimately just a fan of things. I was just so excited to be there, and again, it just became a career but I kind of stumbled into it. I was just genuinely happy to be there just to be a fly on the wall and be a fan. And then over a series of years of sticking around there interning, having low level positions, I turned around a few years later and I'd worked my way up to being a partner in the company. And then I was like, "Wow, well, I guess I turned this genuine interest or passion into a job."

Chris Erwin:

What do you think helped you rise to become partner so quickly?

Aaron Levant:

I think being willing to do anything, being willing to work for free in the beginning and then almost nothing, minimum wage for years after that. You don't have any baggage, I'm like, "I was this important guy in this company, so I will the trash out, right? I will do literally anything." He's like, "Go drive to Orange County and pick up this sample." I'm like, "Great, I'll great there right now." Whatever I could do. I was waiting for someone to hand me the ball, and I would just run with it. I was so excited. There's a famous Biggie Smalls or Notorious B.I.G line where he's talking about you got to treat every day like you're an intern, like it's your first day on the job, right?

Chris Erwin:

Yeah.

Aaron Levant:

I think I genuinely carried that through well beyond the time I was an intern. I think that is what propelled me up, that every time there was an opportunity I raised my hand and ran at it enthusiastically where other people may not have.

Chris Erwin:

Passion was there and it feels like you were just having fun. You were like, "This is cool. This is where I want to be. I'll work for whatever, but I'm doing this with cool people, and I'm all in."

Aaron Levant:

At that time, most of my friends were still in high school and then eventually college, and I was well on my way to making my career, doing cool stuff, traveling around the country, so it was exciting.

Chris Erwin:

Fast forward a bit, and let's talk about the Agenda Show, which was a trade show I think that you were a part of for almost around 15 years. Tell us about what that was and how that came to be.

Aaron Levant:

Through my job at GAT, the founder of GAT was pretty much my first mentor, and I have a series of mentors in my life that really help shape my career and my life, we would go with Luis to a lot of trade shows with his clothing brand. First it was this big show in Las Vegas called the Magic Show, which is the biggest fashion trade show in the world at the time. It would get over 100,000 attendees. We would go to the show in San Diego called the ASR Show, Action Sports Retail. These were B2B marketplaces in the fashion industry for different segments. We would go out as an attendee, as an exhibitor if you will. We'd buy a booth, and we'd sell our wares to the retailers traveling from all over the world.

Aaron Levant:

In probably 2001, I had gone to New York to a really small show called To Be Confirmed, which was some guys from London. They had just rented a loft in Soho instead of some huge show at the Javits Center or the Las Vegas Smith Center, they just got a loft and put up some rolling racks and some table and chairs. They had a cool DJ and bar. I said, "This is pretty fucking cool." I looked around, I was thinking, "How hard is this? You rent an empty room and have some people throw ups some rolling racks and you send out a postcard, you invite some buyers and make a cool ambience." I'm like, "I like this."

Aaron Levant:

That was in the back of my mind. At that time, me and Luis were actually throwing some parties in our warehouse in Downtown LA called Agenda: Art, Music, Beer. It was just something we did as a fun thing to promote our clothing companies. And in 2002, in September, after having a bad experience at the ASR Trade Show, I said to Luis, I said, "Let's turn our Agenda parties into a fashion trade show as a competitor to the BIG Action Sport Show in San Diego." And he said, "Yeah." And in January 2003, a few months later, we rented a Thai restaurant across the street from the BIG Show, invited 30 of our friends. We charged $500 a booth. We weren't really doing it to make money, we just thought we didn't have to pay the other guys $5,000 and we could provide a service to our friends and just do something cool. It just organically just happened. But it was this small little B2B fashion trade show for independent brands that I did when I was 18, 19 years old.

Chris Erwin:

When you had that bad experience at ASR, you have the conversations and you're like, "All right, we're going to launch the Agenda Trade show," Were you excited, were you nervous, were you scared or was it like, "No, I got this. Of course, we're going to crush this."? What was going through your head?

Aaron Levant:

This is a common theme in my career, which some people say ignorance is bliss, I like to say ignorance is rich. What I mean by that is it's like every single thing I've done, I don't know anything about. When you know too much about something, you become institutionalized with fear or they say paralysis by analysis, right?

Chris Erwin:

Yes.

Aaron Levant:

Because I knew nothing putting on an event or trade show, I wasn't scared of it, and I didn't know to be corky or to be fearful or have any expectation. I just did it and didn't think about it that much. It just happened, and it was luckily successful, but I'm sure it wasn't perfectly executed or anything that way. But I just run into things head first, run into a lot of problems, and don't really do too much research in front end because when you do you seem to scare yourself or psyche yourself out of doing whatever that said thing you're going to do. And I've done that a few times in my career where I don't know anything about it, and I've been successful than sometimes people who do know something about it because they're institutionalized with fear.

Chris Erwin:

Institutionalized with fear, I really like that. I just wrote down ignorance is rich. I think that's a fantastic phrase. All right, so at Agenda, it seems that you go through a eight to 10 year period of expansion and then realizing, hey, we have to move the venue from San Diego to Long Beach and then into Vegas. You're collaborating but then you're also expanding and some new competition is coming. And there's a lot of details I'll probably skip over here, but along that journey, what are a couple of moments that really stand out to you?

Aaron Levant:

Three key things. One, I did the business completely independently, first with me and Luis and then later with me and my cousin. I still lived in my parent's house. Any business that people think about now in the world that we operate in, they raise capital, they raise seed money, they raise a Series A, they've got a burn rate. All these businesses have a finite amount of time if they're going to make it or not make it before they basically have to shut down operations or become profitable, right?

Chris Erwin:

Yeah.

Aaron Levant:

I didn't have that. I didn't even understand that as a concept, so I just kept going even when it was going good and not going bad. I carried that forward for so many years, so many times we weren't making money because we didn't really have many employees, I lived at home with my parents until I was 23 or something. It allowed us to push past the point where most businesses would have given up and go, "Oh, the margin isn't growing, or revenues aren't growing at the right rate." We had no analysis of the business. It was an overwhelming theme that allowed us to ever keep pushing forward, probably sillily at some points, to get to a point where we got actually really successful to then where we almost had to shut because the competition got so fierce.

Aaron Levant:

In that moment in 2009 when our business was on the brink of going out of business, I think the defining moment for us was we finally pushed further enough and had this organic growth trajectory over many, many years, almost six years at that point, that I met a guy, Roger Wyett and Paul Gomez from Nike and Hurley, and they offered us an opportunity to stop being the small show across the street from the BIG Show. And this was the big judo business moment for us, which was they said, "Hey, how about you step out of this role you're in as being the parasite... " Or I call it the little sucker fish that swims along on the shark. We're all this little cool thing happening across the street from these big behemoth thing. They said, "Why don't you come with us? You bring Agenda to the US Open of Surfing, which is the biggest action sports consumer event in the world. You should put your trade show in the middle of it, there's a half a million people that will be there."

Aaron Levant:

That was a big departure for us. We were in the verge of going out of business with this one business model we knew, but we were making money finally. And it was like this jump. It was like we had to take this leap off the cliff, and it was either going to work or we were going to be dead in the water. But we're almost going to be dead in the water anyway. So we made this jump and in one year of doing this our business grew 2,000% and we put ASR out of business, which is the company that been in business for 30-something years before that, owned by Nielsen Business Media. It was a huge company, established, respected company by all means. It was this moment where everything changed in our favor and it was almost unprecedented.

Aaron Levant:

So I think that was for me the real lesson there is to take those big risks, to do something that literally was going to sink the company or save the company and has inspired me to continue to do things that throughout my career. But without that moment, I wouldn't be sitting here today. I never would have done probably anything I've done after that.

Chris Erwin:

I think it's a takeaway that I'm definitely hearing, it just goes back to what you said, again, like ignorance is rich, because you weren't looking at the business of saying, "What are the right metrics and all of that?" Where if you were looking at it through lens or had different training up to that point you would have shut it down. But you were building a brand, and you guys were just like, "No, there's something here. There's something here." Sometimes early stage businesses, they just need longevity, like stick around enough because most just shut down within three to five years. But with longevity, other opportunities or other ways of thinking about what you have and how it can work and this duo coming from Nike Hurley and saying, "Hey, guys, here's another approach." And you're like, "That's a great idea, let's do it." And it just happens.

Aaron Levant:

Yeah, that one moment literally defined everything for me professionally, financially. But if we didn't make that far, we never would have had that chance. Even in that moment it was risky, the best risk I ever take.

Chris Erwin:

So it continues to grow and then you eventually sell to Reed Exhibitions in 2012. What was the reason for that?

Aaron Levant:

Up until that point, from 2003 end of 2012, we sold the end of December, the day before Christmas we signed the papers, the businesses was completely built independently, no loans from family, no lines of credit, no investors, no nothing. It was just me and my cousin. We owned 100% of the business. We financed the business. It was starting to get big. We were doing millions and millions of dollars in business, tens of millions and was making real EBITDA, but it was one of those things that it's risky and there's our cashflow that was on the line, right? We had built something that was fairly profitable and weighed the risk of... We had just gotten out of the 2008 financial crisis. We saw a lot of bad stuff happen with that. I lived through seeing what happens during 9/11, right? There's all these things that come in.

Aaron Levant:

We're on this incredible ride, we're making so much money, and we just did the math and said, "Hey, we can continue to do this on our way and carry the risk and something can happen and we can all the value, or we can extrapolate the value now." And I think we did some quick backing up in that. We figured we'd make more money and a lower tax rate than we could in six years if we sold the businesses today, if we kept operating it, right?

Chris Erwin:

Yeah.

Aaron Levant:

And there's lots of unknowns in the next six years. Which I'm actually lucky because the business did down trend in the six years following that. It was a calculated financial risk, and I had a bigger vision for the company than my cousin did. He was very risk adverse, also because we owned it independently and it was all our own money and capital on the line. We were just operating four shows when we sold. I took it, after I sold it, to about 30 shows. He didn't want to go along with those things, so ultimately we sold. He exited the business, and I went with Reed and built a whole portfolio of new products, consumer-facing products, conferences, video products. I had a much bigger vision than what we were doing in this small mom-and-pop shop. So I think it really allowed us to take the financial risk off the table and set us up fairly well, but also allowed me to really chase the bigger vision that I had for the company.

Chris Erwin:

Speaking of risk appetite, it seems that there's this constant leveling up or laddering up where it's like, 'I'm going to try something, and then have a bigger win and then a bigger win and then next."

Aaron Levant:

It's called gambling.

Chris Erwin:

Got it.

Aaron Levant:

It's not a healthy-

Chris Erwin:

So yeah, the question is, was your risk appetite growing where you felt like, "Hey, as an entrepreneur, as a business leader, I'm increasingly capable and I want to take bigger bets."?

Aaron Levant:

Absolutely. In every situation in my career, if I had the opportunity to spend 100 I'd spend 100. My cousin would say, "Spend zero." We end up spending 50. It was a good yin yang balance, right? But at a certain point, when your business is hot and you have that moment, there's a reason they say, "Strike while the iron's hot." Right? Every time we had that, that's when I say, "Let's go. Let's double down. Let's quadruple down." He didn't want to go, and I think I've always been in favor of going. I've lost a lot too, don't get me wrong. I've had plenty of horrible ideas but, true believer, you're not going to get anywhere, you're not going to build anything meaningful, anything big by not doing that fairly often, by putting it on the line and rolling the dice on that. I'm a huge proponent of doing that as much as you can without being completely irresponsible, but you have to be slightly irresponsible.

Chris Erwin:

And maybe we'll get into this as you describe how you built the NTWRK executive team, but do you like having people around you that actually push you even harder and saying, "Yeah, that's a good idea, but here's even bigger, Aaron." Or do you like people that pull you back and then have debate about what's the best path forward? How do you like to build leadership around you?

Aaron Levant:

I think you got to mix of both. You've got some really good financial people that are helping me keep an eye on whatever that may be, the margin or the burn rate or things like that to make sure that I'm not completely unchecked and doing completely frivolous things. But, yeah, I mean, I think I love having people around me who are more aggressive, who have bigger goals, who are uninterested in doing small things, especially investors, right? You get that internally from staff, like my partner here Moksha Fitzgibbons who's the president of NTWRK, constantly pushing. I thought I was aggressive, he's more aggressive than I am, constantly pushing the envelope, trying to push us to do bigger, faster, be more aspirational. And then our investors who have done all the billion dollar businesses where they're like, "Yeah, that's cute what you're doing, but this doesn't interest us unless it gets X big."

Aaron Levant:

I love that kind of challenge because it makes me try to think bigger where what may be relative success to me on a scale of my career, to them is a blip on the radar. It aspires me to want to do bigger or to make a bigger impact and create larger brand awareness and to take that bigger Hail Mary pass if you will. I need those people around me constantly.

Chris Erwin:

All right, so at Reed, you sell Agenda to them but you continued to run the Agenda Trade Show. But then you're also responsible for... I think you launched 30 different events while you're there, including ComplexCon. I mean, I know you're always a dappler and doing different things, but it seems like you were all in on Agenda and now you've got a lot of different babies and children to take care of. How was that transition?

Aaron Levant:

Yeah. I mean, look, I had never finished high school, never went to college, getting to Reed was an amazing opportunity for me because I worked inside a publicly-traded company at a very senior level. It was like going to college, really learning to work in a structure. But also to them they're a $7 billion dollar company. It wasn't just interesting to buy this little portfolio for trade shows and sit on it, right? I had bigger aspirations, and we needed to make bigger to move the needle for them at a corporate level, so they encouraged my bold thinking and they had the finances to go after it.

Aaron Levant:

So we acquired a company called Capsule. We got in a joint venture with Complex on ComplexCon, which is super exciting. I launched a educational conference called the Agenda Emerge, which is like Ted Talks for fashion entrepreneurialism and a media brand around that. So all the above, every single way they could they would encourage me to go bigger, faster, think internationally, and really push my ideas to the brink of where they could go.

Chris Erwin:

What a great partnership because sometimes joining a bigger corporate, they want to throttle you. Things are more controlled, more measured. But it seems like for the type of leader you are and your ambitions, it was a great partnership that actually propelled you and gave you experience I think that was really setting you up for your next phase, which is taking a digital business which was Complex, which I know did start back in 2003 as a print magazine, but it became a huge digital business and then your role was like, "All right, how do we create an incredible RoL event for it. So talk about how ComplexCon came to be. I'm just curious, what was in that initial pitch? What were you thinking?

Aaron Levant:

The interesting part about selling my company to Reed is that they own all of the Comicons around the world. They own 500 major events, many of which are consumer facing and they really focus them around passionate fan communities, what they call fandom. So it's like packs for video games, New York Comicon, Star Wars Celebration. I learned about this event format, which is really new to me because I was in B2B, and I said, "I wonder if Agenda could become... " And this is also part of the inspiration for something like the Comicon for sneaker heads.

Aaron Levant:

But I realized that Agenda been building itself in the industry, we didn't have a consumer affinity. So I struggled to say, "How can Agenda do what Comicon's doing?" This light bulb went on in a conversation I was having with another one of my mentors, which is Marc Ecko the founder of Complex Media. We were at this event in LA, and I just said, "Well, why don't we get together and do ComplexCon." Right?

Chris Erwin:

Yeah.

Aaron Levant:

I said it almost in jest, and he's like, "Yeah, I like that. I like that." Funny standing there with him was Moksha Fitzgibbons who's now the president at NTWRK, and came over and Marc said, "Hey, tell Moksha what you just told me." I told him, they said, "We like that." And they generally encouraged. And then a week later I was in New York. I scrambled for a week, I put together this pitch deck. I got in the room with Rich Antoniello who was the CEO of Complex and Noah who was editor in chief, Marc, and Moksha, and I pitched them this deck.

Aaron Levant:

It was pretty basic. It just basically took the blueprint of Comic-Con and applied it to the brand of Complex. They all loved it. I was surprised because it was just such a bold, ambitious idea. We worked for two years from that point. That was January of 2015 I pitched them, we signed the contract in November of '15, and we launched in November of '16. The funniest part about that conversation which I'll tell you, which is everyone was around the table very engaged. Moksha was sitting on the coach. At very end of the presentation I thought I'd done a great job but he looks over from this Blackberry and says, "How much money are we going to make?" I go like, "Profit? You guys, Complex?" "Yeah." I said, "I don't think, $1 million." And he goes, "Do we really care about making $1 million?" I was so deflated at that point. I thought it wasn't going to happen because he was the Chief Revenue Officer, right?

Chris Erwin:

Yeah.

Aaron Levant:

I was like, "If we don't get his buy-in, this thing's never going to happen." But he actually got on board and was the biggest champion of the thing, and it was an amazing experience. But nothing more than saying, "Hey, let's create the Comic-Con, the fan culture, Superbowl, the world's fair for sneaker and street culture."

Chris Erwin:

The Agenda was a B2B trade show, this was targeting consumers. Where you anxious about, "Oh, wow, how am I going to drive the same type of traffic and hype and momentum around this event?"? Or was it, "No, I can do this. I'll figure it out, I've done it before."?

Aaron Levant:

Well, I think that's exactly what I was saying, that's why I didn't just end up doing call it AgendaCon, right? Complex had the consumer reach and the social media reach and the affinity with consumers, and I had the relationship with the brands and the exhibitors and the know-how in event production, so the marriage was beautiful in that sense. It was bringing my offline experience with their online marketing reach and bringing that. Of course, we did a lot more things that neither of us would do, market it ourself almost like a concept promoter, which is new to both of us. But it was the perfect marriage of their audience and our event expertize. That's really why it worked.

Chris Erwin:

Like you said, when you were at Reed, it was like your MBA. You were like the senior executive of a big public company but you were just doing deals, launching new businesses, and learning a lot about business as you went. This was probably a great change to learn of how can you create an event from a digital business but then really market it through all the paid and earned organic channels. Now thinking about where you in your career, that was probably a great learning experience for you.

Aaron Levant:

Absolutely, right? There's so many learnings in ComplexCon. I think the number one learning for me was as successful as the event was, the digital groundswell that the event created, call it organic customer acquisition, the earned media, that was so big that that was such an eye-opening experience for me, how much the physical world could influence the digital community so much more effectively than just trying to market to people digitally. That was really my big takeaway and a lot of the inspiration for wanting to leave and come join NTWRK.

Chris Erwin:

I know at ComplexCon now with $100 ticket prices and incredible curation of products, there are attendees who will spend days waiting in line so that they can get early access to the different product vendors, right? Did you guys see lines out the door in your first year of ComplexCon?

Aaron Levant:

Yeah, there was thousands of kids lined up around the corner at both sides of the convention center. We had a literal, and I mean this in the most literal sense, a stampede of kids pushing past security, knocking down full-grown security guards, extensions, police officers. People literally almost being trampled to death. It was actually scary. The second year we had people who were stowing away, like when people stow away in a ship.

Chris Erwin:

Yeah.

Aaron Levant:

We had kids who snuck in days before and were hiding in a broom closet so that they can get early access. The level of pandemonium around ComplexCon year one and two and three was just so insane. It was dangerous. There were actually people injured and it was also so amazing to see. I was almost trampled to death in the crowd were people fighting for Pharell sneakers at the Adidas booth. It was pretty insane the level that people go to but also I understand not only the passion and the fandom, but if you can buy a sneaker for let's say $120 and we sell it for 5,000 the next day, then you might be running full speed as well.

Chris Erwin:

Yeah. I imagine you seeing that probably flipped a switch inside you being like, "Well, look at this fan energy and the fandom. There has got to different ways that we can build this to be even bigger and then harness it both in online and real world environments." I think that probably leads, I think, in September 2017 you have a conversation with Jimmy Iovine that you're all starting to think through the new NTWRK business plan, so tell me about that moment.

Aaron Levant:

Jimmy and his son Jamie, who's my partner, had had a previous business in LA called Meltdown, which was a classic comic book stores. Out of this comic book store they were doing a YouTube show that was... call it QVC meets Comic-Con. It actually started to get a little energy and there was an article written in Forbes Magazine saying it was an innovative idea. They had put a little money into it and were trying to launch as a business and had some false starts. But the idea was there. I got interested with Jimmy around this idea that he was working on, which was the Meltdown thing. They said, "What are your thoughts on this?" It was a loose introductory meeting just to talk about this Meltdown concept.

Aaron Levant:

I saw it and I inherently understood it. I thought it was a great concept, but I had a little bit of a broader vision around what I thought NTWRK could be. We ultimately changed the name of the company and changed the focus to not just be Comic-Con pop culture focused, it will be a broader youth culture, sneakers, street wear, entertainment, gaming, right?

Chris Erwin:

Yeah.

Aaron Levant:

This idea of aggregating the most passionate fan audiences into a platform, procuring the most exclusive drops and having the actual talent who created them present it to you on a daily basis, I thought there was huge merit around it. Ultimately, that night I went home, and I wrote a business plan that ultimately ended up being verbatim what we're doing for NTWRK for Meltdown. I was still working at ReedPop at the time. I felt like over the course of the next few months the conversations I had with Jimmy and with Paul Wachter, who's chairman of our board and runs the investment fund, main seed advisors who funded our seed round, I saw one thing clearly. Not only do I think this was a great business idea but I thought for me I'd done a lot of things in my career, and I think ComplexCon was the pinnacle of my career, but I had the opportunity to come and jump on board and work with a group of people who had a bigger creative vision than I had.

Aaron Levant:

While I was at Reed, I was the crazy, creative one in the room, and in the conversation with Jimmy and these guys I was the one who was thinking small. They're the ones who had the big, crazy, creative vision. I liked that, where it putting me back on my back to level up. They had just sold Beats for three and a half billion or whatever that was, and they really are epitome of people who take passion around creative and brand and push it to that main stream level. I had relative success but not that level, right? I wanted to be in the midst of that type of greatness and learn from that to take my career to the next level.

Chris Erwin:

So this happens in September 2017 and then you raise seed round. When does that seed round close and when do you start being all in and focus on NTWRK?

Aaron Levant:

I quit ReedPop in February of 2018 and then worked on refining the business plan on NTWRK for a few months., and then in May of 2018 raised the seed round, and then we launched in beta in October of '18. From May to October built the team, built the kind of MVP product, and just worked on refining what the business was and what the brand was.

Chris Erwin:

How much did you raise in the seed round.

Aaron Levant:

15.

Chris Erwin:

15 million?

Aaron Levant:

Yeah.

Chris Erwin:

What type of team did you assembly around you? I think that was different because you're building a digital product, you hadn't done that before, right?

Aaron Levant:

Yeah, look, there's three things we do at NTWRK that I have almost no experience with, building technology, becoming a media company, and being a retail company in a way, right? I'd been adjacent to a lot of those things. I'd been on the boards of some companies that have done some of those things, but I had never done it. So that's other part of it, it was super exciting for me. Look, we had to hire a whole new team of people who... I prided myself in the event industry, if you want to hire someone, I knew who all the best people were. This was really easy for me. My Rolodex that was really strong. This was like going in unchartered territory so I had to figure out what I was doing and try to find the right people. I think it was a big challenge for me in a good way and challenged me to spend my network, no pun intended, and go out and find new groups of people to talk to.

Aaron Levant:

I never hire usually recruiters or people like that, I always do it through referrals. So this was a process, it was 24/7 process of trying to find new amazing people who came from other great amazing organizations.

Chris Erwin:

Who or what most helpful to you during that time? Was it your board, was it Jimmy? As you were being like, "Okay, I need to have a new muscle to hire these new leaders with capabilities that are unfamiliar to me," what was helpful?

Aaron Levant:

Yeah. I mean, look, everyone was helpful, ultimately just me pounding pavement, picking up the phone, and trying to... Spent a lot of time LinkedIn, just cold hitting people up. Sometimes great people come to you in interesting ways. Our CFO, COO who's still here today, Emerson, came from a referral for Guston who was the original owner of Meltdown, the comic bookstore. You wouldn't think the guy that has comic bookstore's going to find you a CFO, but he actually found us the best guy. Referral and just always going out there and telling everyone you know, whether it's your aunts, uncles, cousins, friends, colleagues what you're looking for and asking who they know and getting people to send you great people is honestly the best way.

Aaron Levant:

Everyone was helpful, the board, the internal staff, and me just literally going on LinkedIn like a crazy person and finding people who like they're impressive and just dropping them a cold line. And then I'd have to try and explain to them, "Hey, I want you to come to this company that doesn't exist, that I can't tell you a lot about yet, and it doesn't have anyone else working here. Are you interested?" That's always the fun processes, getting people to leave their careers. It isn't like I'm the founder of some billion dollar tech unicorn and this is my second thing, right? There is some selling involved here.

Chris Erwin:

But I think that you had had an amazing career to date. You had a pretty rockstar board instead of investors, so when most people heard your pitch, where they like, "Yeah, Aaron, this is exciting, I'm in."? If you were to say the biggest trepidation, people who hesitated, what was the number one reason?

Aaron Levant:

I would say every department but technology has been, I wouldn't say easy, but we could recruit people.

Chris Erwin:

Okay.

Aaron Levant:

Technology is by far the hardest thing because if you're an amazing engineer, if you're an amazing CTO, you're an amazing product person, there's nothing but options for you in this world. Everyone has the same pitch, amazing founders with an amazing backstory, who've had success before, amazing board and tons of money in the bank from some of the top VCs and private equity funds. So, in that case, even though we had a lot of those things, we were in no better footing than anyone else. If anything, we were a step backwards. So I feel like that was the hardest thing, and still is. I think we've come over that hump now. We finally recruited an amazing CTO here at NTWRK, which is Marko who previously led engineering at GOAT for the last six years before joining us, which obviously a very impressive business. But that's probably been the thing that took the longest amount of time.

Chris Erwin:

I just interviewed Christian, the president of Complex, and he said that what's unique about his team is that everyone there is a fan, either they like hip hop, they like street wear culture, they like music. Was there also a through line that you were bringing from like, "Hey, as I've built my career today and for the team that I know that's really going to exceed here, people need to love this intersection of pop culture and commerce entertainment."? Was that important to you?

Aaron Levant:

It's always been important to me. I would say it's become, depending on the role, some places more important. We need the foremost experts, authorities, thought leaders, test-makers in those field and people who are picking the merchandise, people who are having a consumer front facing role in our business and has an effect on what you see on screen and what our customer are consuming. Sometimes I would, in the past, I think it was an immature part of my leadership style, is that I would dismiss amazing people who could bring such value. They came from greatness, right? Some organizations have a culture of greatness and excellence, and I would dismiss those people because they weren't into what I was into.

Aaron Levant:

Often in my career until NTWRK I think overlooked some really amazing people that probably could have helped me along the way. So I think that could be a very arrogant thing to dismiss someone if they don't love sneakers. I don't even really love sneakers to be perfectly honest with you. I think it's both, you need a good mix of finding the best people who are the hardest workers, who are the smartest, who are going to challenge you and bring value to the business and finding the people who are going to help you keep on the center of culture, and blend those people together.

Chris Erwin:

Before moving into some specific work that you're actually doing at NTWRK and some of the partnerships and the launches, what did it feel like to go from a hustler entrepreneur to now a steward of capital? You had raised $15 million in the seed round, it's a big seed. I believe all your other businesses were bootstraps, you weren't representing investors. So what was that shift like for you?

Aaron Levant:

Everything I'd done until Reed was completely independently financed by me, and I treated those like real scrappy, scrappy, scrappy businesses, right?

Chris Erwin:

Yeah.

Aaron Levant:

I was fighting tooth or nail for everything down to what I was paying for an office chair. If someone tried to order a $50 office chair online, I'm like, "You can get it for $38 at Ikea." Those little things, right?

Chris Erwin:

Yeah.

Aaron Levant:

My cousin used to call it the million dollar loaf of bread. It's these little things that add up to all of a sudden you've spent a million and you're regretting it. So I was real scrappy in my entrepreneurial days. At Reed, I was scrappy but I definitely learned to be a shepherd of capital in that I was working a publicly-traded company and there's a lot of process there. So I think the two things really set me up well. I understood how to work with large amounts of money at Reed, and I understood how to be a scrappy entrepreneur in my whole previous career. I think I applied both of those things well here. And I went back to trying to be scrappy to the point where even sometimes the board would say, "Aaron, you're being a little too scrappy. You got to spend some money. We gave you all this money, you got to actually buy some Herman Miller chairs." Whatever the analogy is right? It's not all about chairs but I like to use that as the analogy for frivolous spending.

Aaron Levant:

Look, I feel every day utterly responsible for the investors who gave us money and the LPs for the funds that I need to deliver for them. I put that pressure on myself every day to an extreme extent that I need to return. Like, "Oh, this VCs getting money, whatever, it doesn't work out, one in 10, they'll get their money back." I don't think about it like that, and I hope nobody does who's a CEO. But I feel an absolute personal obligation to deliver minimum tenfold for everybody.

Chris Erwin:

For the investors who will listen to this, I think they're going to be very happy to hear that sentiment. What also comes out here is that these new investors like Jimmy and Warner Brothers Digital and LeBron also want speed. For a return on capital, it's like "Aaron, yes, being prudent is great, but just move fast. You're on to something and we're betting on you. If you're going to help build this market, and so speed is a major asset." I think that starts to show its face because then you raised pretty quickly after your seed, you then raise a 10 million series A in September of 2019. So that I think that is led by Live Nation and Foot Locker and Drake's also involved. At this point, what are you now building towards, and what are some of the key build highlights that are now setting you up for what we're going to talk about is where NTWRK going in the future?

Aaron Levant:

What we're really building for is to build the definitive marketplace for youth culture amongst the coolest personalities and pop culture goods, the most sought-after drops and releases across every category that we think is cool, right?

Chris Erwin:

Yeah.

Aaron Levant:

And that's a pretty expansive view. I think we aggregating, much like I did at Agenda or ComplexCon, we're finding these passion audiences, we're convincing the most meaningful players in those audiences to create special site specific drops and things for this platform, and now we're just doing in a digital way under much more expansive amount of categories.

Aaron Levant:

We got the proof of concept in 2018 and '19 and now it's just about now it's just about how do we scale that, how do we get more people on the platform, how do we go from one drop a day to 40 drops a day is what our hope is by the end of next year, 40 unique, specific, custom, exclusive things in one day is a lot, right?

Chris Erwin:

And to do it over and over again. It's not like you're just building up towards one single day a few months out, it's like this is a daily thing?

Aaron Levant:

Yeah. And how do we make each one of those not only equal quality, how do we increase the quality over time and how do we take this from a few million people to tens of millions of people, and we become for the overused elevator pitch about our business, the QVC of Gen Z? I think that is exactly what we're trying to do and I don't take objection to that elevator pitch, I actually like it.

Chris Erwin:

As you think about going from one drop a day to 40 days a day, is there data from the performance of your past drop campaigns of what is selling, what is driving user acquisition that you're using as a data feedback loop and/or is it also a combination of just going gut of like, "This is a cool product, I dig it, we're going to launch with this too."? What is that approach?

Aaron Levant:

I would say it's 50% gut, 50% data at this point. I think over time it'll become more data. In the beginning it was probably 100% gut because we had no data. Obviously, it's taking learnings from the things that are working, the categories, the personalities. There's a lot of learnings in there around how we scale this business and there's also a lot of surprises, right? I think some of the biggest surprises we learn is just because X celebrity has a big audience, it doesn't mean they sell anything or anyone wants to buy anything from them. There are many personalities that have a much smaller audience, maybe just a few 100,000, that can sell 10X any big celebrity, because they have hyper-engaged audience, an organic audience.

Aaron Levant:

I think that's been one of the biggest surprises. I think one of our biggest aha moments was in 2018, Ninja was the biggest esport star in the world. He's still a huge star, right? We were like, "Oh my God, if we could just get Ninja to come on NTWRK and sell some stuff," when he was on the Ellen Show and breaking the internet, "we'll get a million downloads in one day, right?"

Chris Erwin:

Yeah.

Aaron Levant:

We go, we do this deal with him, we get him on and he's got an exclusive collection for us for holiday and 50 people came. It was nothing, right?

Chris Erwin:

Yeah.

Aaron Levant:

New people. It was ridiculously low and it was like, "Wow, it's like sometimes these people that are so big actually don't move culture in a way that you think they do. They're propped up stars for consumption and click-bait but they're not really able to have a meaningful consumer products business." So sometimes you can't just go off the data of how big their social audience is or what their engagement looks like online, things like that, you have to some gut around, do people actually want to buy products from them? I think there's a lot of example of big celebrities who are very much household names but couldn't sell anything. And then there's some people that can create a brand that does billions of dollars, right?

Chris Erwin:

Wow. Yeah.

Aaron Levant:

So it's a real hit or miss there and that's really part gut. That almost becomes the more important part.

Chris Erwin:

It's interesting hearing about that because at my company, RockWater, we are helping different shoppable entertainment companies think about what their go to market launch is. And so we've been reviewing tens of these different live streaming content products. And we're seeing that some of the platforms actually audit the different types of creators or influencers that are onboarding and saying, "Are you a good fit? Are you not a good fit? If we think that you're going to be a premium creator you'll get more customer service resources and we're going to help prop you up." Has your team built any proprietary tech or methods of how you assess the personalities who are going to do a product collaborations with your team?

Aaron Levant:

I wouldn't say we're assessing them beforehand. We definitely have the post data where we've worked with them. But I would say here's the counterpoint to that even. I'll give you another example, the most successful individual personality on our platform beside Takashi Murakami, is a guy named Ben Baller, who's a celebrity jeweler, podcaster, all around personality. He has a big consumer products business with us. He's been on NTWRK for six months doing multiple things and almost all of them didn't do very well in the beginning. We kept sticking with him against the lack of positive data, right? It wasn't selling through, the audience wasn't engaging. And then eventually we had a breakthrough moment with him. I equate this almost the Agenda thing, you keep pushing forward and we always had a feeling or I had a feeling this guy was working to work and now he's our number two star on the whole platform from a revenue basis.

Chris Erwin:

What was in your gut that kept you sticking with him, similar to when you were at Agenda? Was it the ignorance is rich, like "No, I believe in this guy, I like him," or was there something else going on?

Aaron Levant:

Yeah, I believe in him. He was enthusiastic about the partnership, right?

Chris Erwin:

Yeah.

Aaron Levant:

Some people, some celebrities they do these things and it's like an obligation. They go, "I got to show up and do this thing and sell this book." They pretend like they're enthusiastic but really they're not. They do the bare minimum. They're like, "oh, I'm obligated to do one social post, I'm going to do just that and then I'm going to take it down." Those people that are going to fight to make their things work. They're going and doing... like GaryVee, great example, that guy is a salesman of salesmen, right?

Chris Erwin:

Yeah.

Aaron Levant:

He gets on and he's going to pitch himself like nobody. DJ Khaled, Ben Baller's one of them. They're enthusiastic and they're going to go above and beyond tenfold. And it knew that eventually it would break through, and it did. There were even people inside our own org who tried to kill the partnership, go, "Hey, this guy's not working. We've got all these other products on him, let's put these on the shelf, right?"

Chris Erwin:

Yeah.

Aaron Levant:

"Let's not push forward." I'm like, "No, you got to do it." It wasn't anything other than just seeing his level of enthusiasm towards the partnership. I believe that you can bank on that.

Chris Erwin:

The talent enthusiasm is so key because they have so many opportunities in front of them nowadays of how many different social platforms that they're on, how many different advertisers they can work with, what products can they launch. I remember when I was running Big Frame, the management company under Awesomeness TV, partners would come up to me and ask, "How do I work with your talent? How is this going to be a thriving partnership?" I would always, "You got to sell them on your product and on your vision and not just throw money at them." I would often nix them like, "Hey, if our sales team was pushing too hard," of like this was a big six or seven figure dea where our managers knew that the talent weren't really into it, I'm like, "We shouldn't do this because this is just going to fail and both sides are going to walk away unhappy."

Chris Erwin:

So I like how you described the enthusiasm is so key. Curious to talk about the future vision for NTWRK and some of the things that you're building towards. I've heard you talk about that you want to festivalize marketing and user acquisition. And I think that there's definitely intent to have many more shopping festivals I think in the new year. Tell us a little bit more about what's your thinking there.

Aaron Levant:

One of the things that I was obsessed with from day one, even in the original business plan, was looking at things like Alibaba's Singles' Day, which obviously has become since the last three years much more well known thing here in the US, and they made $75 billion this year, I think. They made a week-long event, previous iterations it was a day long event, they made $35 billion. They really took something that was like Black Friday or Cyber Monday here in the US and they made it look like the MTV Music Awards. It was a video first event, it was live stream, and it was crazy, right? And how they entertanmenize shopping, right?

Chris Erwin:

Yeah.

Aaron Levant:

I took how you took something like a ComplexCon, something like an Alibaba Singles Day and make a marriage between those two ideas and you launch an online shopping festival. That's really what we're doing with NTWRK. In the coming year we're launching six proprietary shopping festivals, each one around a different audience vertical and two big shopping holidays. These are big ideas for us. We did our first one this year called Transfer in August, which was a design and culture festival in partnership with a creative named Edison Chan from Hong Kong and the artist named Futura 2000, which was an amazing event. We had over two billion media impressions on that event, so we were excited about that. We're launching one just a few weeks here called Beyond the Streets which is an online art fare that's themed around street art and graffiti, which previously was a physical event that now we've brought online. And next year we'll have six. We'll do one called Unboxed in February that's themed around collectables and toys.

Aaron Levant:

We'll do one in March or April called Off Court which is focused basketball culture. Really about packing two days full of content, meaning dozens or almost 50 to 70 exclusive drops in a two-day period, bringing in the talent who created those drops or musicians, athletes, artists to do panel conversations much like we would at some of my physical conventions or festivals in the past, having live music performances, having a gift shop, having physical takeaways we send the people in the mail beforehand, and really entertainminizing and festivalizing this online shopping experience. It's really about taking hundreds of pieces of content that you can usually absorb over the cause of a month and smashing it into a two-day period and creating sensory overload. We're excited about what that does for the businesses on the go forward and how that draws new customers and how that creates excitement, and also stimulates brands and creators who want to work with us, right?

Aaron Levant:

If you just called and said, "Hey, you want to do something on a Wednesday because it's Wednesday." They're like, "Ah." You call them and say, "You want to be a part of this festival and all the top brands and creators in the world will be there?" It's much more motivating value proposition.

Chris Erwin:

Are you building this online experience in tech in-house or you're working with a partner to do it?

Aaron Levant:

It all lives on networks made of IOS and Android platforms, so it's literally sitting right on top of our day-in and day-out platform. It's not a separate experience. And that's the whole point. The whole purpose of this is to draw people into what we do and to utilize the technology and the proprietary native commerce and video technology we build here.

Chris Erwin:

You are planning six of those events in 2021.

Aaron Levant:

Six festivals and two shopping days, which is a one-day festival. For example, 10/10 is NTWRK's birthday, so that our annual celebration where we do a huge promotion. We don't want to be a retail company, I think that's a dead asset class, I think it's a boring idea. I think the number one thing for us to do that is we're creating these moments. We'll do some of the standard retail things like Black Friday, Cyber Monday, Back To School, whatever, but how we create our own moments and we create our own annualized trend. What if we stacked all of our festivals in the first quarter, which is usually the lightest quarter for retail, what if we could buck that trend by doing all this exciting stuff.

Aaron Levant:

So we're creating our own retail holidays and creating our own trajectory of what we do and when we do it. We don't want to prescribe to what Macy's does per se.

Chris Erwin:

I was going to ask how you gauge success of that. ComplexCon will talk about, "Hey, we drive 20 to 30 million of merchandise sales in Long Beach and we're the number one contributor to that economy." Are the KPIs for you, it's revenue but also how it fuels the rest of the business or ability to attract different artists and personalities to the platform for the new year?

Aaron Levant:

It's all the above. Obviously revenue is an important KPI. Transfer for example was our highest two days of revenue ever during our last festival. Obviously we intend to beat that coming up in the new year. User acquisition, earned media. We had, like I said, two billion media impressions on that. It's also about how many new brands we attract to the platform, new talents, because then those people could have an ongoing relationship with us. Even things like Google Trends data, if you look at the dates around Transfer, some of our highest searches were NTWRK, right? So all of the things are extremely important KPIs or metrics we're going to track, but we want them all. I think that's a great thing about a festival, it solves for every meaningful thing we want to track in the business, the businesses just accelerates that.

Chris Erwin:

Let's also talk about another big initiative for the company which was your April 2020 investment in FaZe Clan, one of the world's largest esports and gaming collectives. If I understand this right, it was a $40 million round for FaZe Clan and you guys were the lead investor, is that accurate?

Aaron Levant:

Yes. Absolutely.

Chris Erwin:

What's the strategy where NTWRK is defining shoppable entertainment and shopping at the speed of culture, and now you're also making a really big investment in esports and gaming company? What is the goal of that?

Aaron Levant:

I think it's a pretty simple idea, which is we want to be at the forefront of what's happening in youth culture. I liken FaZe Clan as the leading brand in what is arguably the fastest growing space in media and entertainment, which is gaming lifestyle, esports, right? The numbers are astronomical, so when we think about attracting new audiences that are passionate about something, to me it's esports is the skateboarding of the day, right?

Chris Erwin:

Yeah.

Aaron Levant:

This is the thing that captures the hearts and minds of possibly billions of people, right?

Chris Erwin:

Yeah.

Aaron Levant:

Not just millions, it's a much bigger totally addressable audience here and why not partner with the top brand and organization and the largest brand and organization in that space. The analogy I like to use is that Netflix brings disruption to video streaming, Spotify to audio streaming, NTWRK is trying to do for merchandise streaming, right?

Chris Erwin:

Yeah.

Aaron Levant:

This is the category that doesn't really exist. So what makes those platforms destinations is the proprietary content that they have. It's not that we make an investment in a great organization, but we also secured a deal to control the global consumer products rights for that company. And so right now if you go on NTWRK and you scroll down through our feed in couple days from now, we're dropping an exclusive FaZe Clan Beats by Dre headphone exclusively on NTWRK. So when you think about us bringing together a collaboration like that, first time Beats has ever been in the gaming space. Obviously, Jimmy, our lead investor was the founder of Beats, bringing together with the top gaming organization in the world and you can only buy that product on NTWRK. Same analogy like you can only watch Game of Thrones on HBO or you can only watch House of Cards on Netflix. Proprietary content drives new audience and drives revenue and drive retention.

Aaron Levant:

So how do we as NTWRK strike multiple exclusive deals with meaningful brands, creators, organizations that you can only buy their things on our platform and that gives us product or content exclusivity, which is going to be the moat around the business as we grow. I think there's many platforms that have "shoppable video" I think we have better shoppable videos than others, but you'll be able to buy stuff on any number of video or social platforms in the future. But if we have things that you cannot buy on Instagram or you cannot buy on YouTube, that you cannot in those places, then you have to come to NTWRK, and that is through a meaningful value proposition and moat that we can offer in the future as video commerce becomes a commoditized proposition.

Chris Erwin:

Are there plans to make other investments like what you did in FaZe Clan going forward?

Aaron Levant:

I don't know if we'll make other investments. I think FaZe Clan is unique. But I think you'll see us making many exclusive distribution deals and signing creators per se. FaZe Clan is unique because they have an organization of dozens of creators, right?

Chris Erwin:

Yeah.

Aaron Levant:

So that's in our larger one. But I think it's just making deals with individual creators or individual brands. A necessary is probably an exclusive licensing or exclusive distribution deals.

Chris Erwin:

As you think about where you want the NTWRK experience to go, I have heard you talk about this all about just delight the user, delight the consumer, make the shopping experience fun and sticky in that they want to return and that it's also a valuable form of expression, like their identity. So what are other ways to build towards that, where you're like, We're not here yet, but in three years I really want to have this be part of the experience."

Aaron Levant:

It's a combination of multiple things. Right now I think we've done a good job of getting amazing products. I think we have an area to improve on which is making the content as entertaining as the products are amazing. As you can start to create that marriage of true... people start showing up in the platform just to be entertained and then they also certainly want to buy, I think that becomes one plus one equals 10. I think the festivals are really the first step in heading in that direction where we're creating the term retailtainment, and we can be a true retailtainment company and be at that forefront of that movement, I think that that is probably one of the most things in us continuing to invest and maybe instead of doing six festivals we're doing 10 or 20 because there's so many passionate audiences out there we can cater to.

Aaron Levant:

We did one this week for Japanese anime, which was a highly engaged media genre. But I think it's a combination of having amazing and proprietary products, having an amazing entertainment experience, and doing both of those things at scale and continuing to move into new verticals. In the future we see beauty as a vertical that is just as engaged as, let's say, sneakers. I think there's endless amounts of creators and passionate fan communities that make sense for what we're doing, and we are just scratching the surface. I think people probably look at our business from the outside in and think it's very male, sneaker street wear focused. And honestly, sneakers is less than 8% of our business right now. Things like toys and collectible is by far our largest category and I'm not sure if people would think about it that way. That's everything from a $500 Bare-Brink to a $15 Funko toy. By transition volume and by revenue, by far our largest categories.

Chris Erwin:

Interesting. Just a couple more questions before we get into rapid fire and close this out Erin. I liked what you said about redefining the content experience. I was actually just interviewing Michael Gaston who is the former founder and DCEO of Cut.com and now he's a head of studios at Stage 10, which is a live streaming platform, and they're also making moves into commerce as well with Rosie, which is maybe coming out in the next six months. What I've heard him talk about but also other executives is what are the owned and operated content formats that are really going to propel the live stream shoppable entertainment space forward? Because it's not just like, "Oh, well, what about the formats on YouTube, the inboxings or what's inside. It's like, "No, there's got be new formats that are really unique to the new technology solutions that are coming in the space. And these new formats can be seeded and incubated at all different platforms but they can exist everywhere. That's a win because that'll push the whole industry forward.

Chris Erwin:

I don't know if that's part of maybe your hiring plan for thinking about NTWRK as a content studio and having a real creative to run that, but I like where your heads at there.

Aaron Levant:

Content has been at the front of our mind and we've had various different content formats and we continue to have them some scrappy low-fi digital contents, just some stuff that looks like a beautiful docu-series that we've done with Nike, right?

Chris Erwin:

Yeah.

Aaron Levant:

I think we'll continue to experiment. We've had great people that continue to work who came from Vice from Complex, some of the best digital content companies in the world and we'll continue to hire more producers and creatives from those companies. I think in terms of formats, I was equally inspired by HQ Trivia as a content format, a truly interactive appointment based, energetic jeopardy for the mobile first generation, right?

Chris Erwin:

Yeah.

Aaron Levant:

That has a real tangible UI/UX experience that ties with the content. I think you'll see us doing stuff in that vain in the future. And honestly, when I wrote down in the very beginning it was like QVC and HQ Trivia as a format on screen, right?

Chris Erwin:

Yeah.

Aaron Levant:

It's the vertical host and you're asking questions, so I think that's something we're thinking about a lot as much as we're thinking about gleaming insights on content from traditional television. One of the number one things I want to launch on NTWRK over the course of the next year or so is a late night talk show format, which is a Jay Leno, David Letterman style show. What is that show to me? It's celebrities coming on when they have something to sell. They there to sell a book, a movie, an album. They do the interview, it's engaging, that's why the audience there, and then they hold it up, they say, "go buy this book at Amazon," and they cut to commercial. Why do we not give you that meaningful interview experience and we sell you the book and we sell you the toy from the movie that Robert Downey Jr was there. We sell the Avengers story.

Aaron Levant:

I think we're looking at actually a lot of breakdowns of traditional linear formats and I think we'll be successful on a platform like ours where there's a real call to action to purchase.

Chris Erwin:

As you guys continue to invest in that and become more and more a media company, the idea to also syndicate, if this is part of your marketing strategy, to syndicate your content and those experiences to other platforms. I know you did a partnership with TikTok recently. Could you be syndicating to Facebook, to Instagram, to other emerging live stream shopping companies that is not only propelling up the industry but it's building brand awareness for you across a distributed network, but still driving the most activity towards the NTWRK app?

Aaron Levant:

Yeah, you're about to see us launch just series of content, I believe this month if not early next month through Snapchat. We've got a series of shows called the art of the drop that are releasing with Snapchat, doing exactly what you said, working with our stable of creators and exclusive products and releasing them on Snapchat. We see that as largely brand awareness, great ways to get in front of a new eyeballs and hopefully drive people back to our native platform. I think our sole focus though is driving people to our native platform because the trends change. It went from Facebook to Instagram to Vine for a second, back to Instagram, to Snapchat to TikTok. It's an ever-revolving spin. It's like you don't really ever own your audience there, right? So us spending a lot of time, money, or energy in building an audience in any of those platforms is not a high priority for it.

Chris Erwin:

Got it.

Aaron Levant:

Because we are own platform. We have a direct relationship with our consumer and no one can make us pay to get past an algorithm to reach our people, so it's always going to be more valuable for us to build our proprietary audience in our proprietary platform.

Chris Erwin:

Aaron, last question, before we go into the rapid fire. I have heard you talk about your career in thirds. There is intent in your final third to want to give back in a very meaningful way. And so I'm curious when you hear about Supreme selling to VF for $2 billion, what is the plan for NTWRK? How would you describe success over the next five to 10 years for NTWRK, that's not only a win for your investors, the users and your team, but also for you to get into this next third of your career. Like to hear a little bit more about that.

Aaron Levant:

I think that comment is largely driven by, I have no illusion that majority of what I've done in my career while it's been satisfying personally or financially to a certain extent, I've ultimately done a lot of pointless stuff, which is helped a bunch of teenagers buy cool T-shirts and sneakers in various forums. And while I have an affinity for that, I think that I aspire to do something more meaningful with my life on this planet. So I think of what I'm doing with NTWRK and this stage of my professional career as one, I'm still fairly young in the big scheme of things. At 37, I got a lot of life left in front of me. I would like to, at a certain point, exit from this type of professional life and enter full-time doing philanthropy. But I also think that one thing I committed to when helping get NTWRK off the ground was injecting a certain amount of philanthropy or philanthropic projects through this lens.

Aaron Levant:

And I thought, what a great way to raise money, plus just asking people for donations. I could go find me a model selling extremely cool things for charity, right?

Chris Erwin:

Yeah.

Aaron Levant:

You've seen companies like Ren do a great job of that. We were really lucky earlier this year to work with Japanese artists, Takashi Murakami on a charity project that we raised money for a social justice and Black Lives Matter related causes. And we gave $1.4 million away to charity through the result of that project we did with them, which is a huge actual donation amount. A lot of people raise money, but sometimes the actual donation was a bit smaller after all the costs and things like that. So our goal and aspiration is to raise millions of dollars per year through NTWRK, working with all these cool brands and creators making products that are specifically designed to raise funds for meaningful causes, whether those are environmental causes, various number of things that are important to us here.

Aaron Levant:

And I think this is a great platform to do it. When you think about what you used to see as like the Jerry Lewis telethon, you see these video formats, "Call us now," There's a phone bank of celebrities. What a great platform, we can take your credit card, sell you something cool. And we all started doing direct donation buttons inside the app now. So I think there's a lot you'll see, almost like telethon S things coming to NTWRK that at least makes me feel like a bridge between what I ultimately want to do and what we do now for a job

Chris Erwin:

You're reinventing the fundraising model. And you're setting up your next third concurrently. Aaron, let's get into the rapid fire. All right. So this is around six questions, really short answers, a couple of words or a couple sentences max. You ready for it?

Aaron Levant:

Yep.

Chris Erwin:

Proudest life moment.

Aaron Levant:

I don't know my life moment. Best professional moment would be the launch of the agenda emerge conference.

Chris Erwin:

What do you want to do less of in 2021?

Aaron Levant:

Stare at my phone for endless hours a day. And the screen time app is not helping me do that as effectively as I'd like.

Chris Erwin:

I hear that answer quite often. What do you want to do more of in 2021

Aaron Levant:

Spend more meaningful time with people that I care about, friends and family, not looking at my phone.

Chris Erwin:

What one thing drives your success in your opinion?

Aaron Levant:

Insatiable appetite for being competitive and winning.

Chris Erwin:

Advice for media and commerce execs going into 2021.

Aaron Levant:

Don't do boring shit.

Chris Erwin:

I like it. I mean, that's the experience of NTWRK. It's like have fun with it, make something cool. Last two here. Any future specific startup ambition?

Aaron Levant:

Always. I have a book with about 20 ideas in it. We'll never have the time to do, but I have a multiple on my list.

Chris Erwin:

To be clear, always more to come from Aaron Levant all right. Last one, this is an easy one. How can people get in touch with you?

Aaron Levant:

I am not really on social media. I don't really have a public facing profile, but they're more than welcome to email [email protected] and someone will forward it to me.

Chris Erwin:

Got it. Aaron, this has been a delight and a really fun conversation. Your story is just such a wild adventure. So thanks for spending time with us.

Aaron Levant:

Thanks for having me.

Chris Erwin:

What another fun interview. So after having done a handful of these, what's just so interesting about Aaron is that he was just a hustler and a fan since very early days. And didn't have the traditional academic rooming to be an executive or anything like that, no formal professional training programs. He just tried things at an early age like that car magazine, and then just followed his love for street wear culture, pop culture, music, and started building things. And yeah, he tells a great tale. And it was really fun to dig and better understand how NTWRK came to be dating back just like, I think a little over a couple of years ago.

Those early conversations with Jimmy Iovine and then having to recruit executives that had had different expertise and he had worked with before. And then just what he's working towards in the future. The festivalization, the six shopping festivals coming up in 2021, trying to have Alibaba's Singles' Day meet ComplexCon. And thinking about the new content formats that they're working on, it's syndicating that to Snap and Twitter, just really cool stuff. And it was fun to hear about how he wants to give back in his final career third.

That was awesome. And think that he's going to likely participate in our upcoming live stream media and commerce conference. So more to come on that from us. If you're just in getting involved and want to learn more about it, maybe you want to speak at it, you can reach out to us at [email protected]. All right. All that's it. Thanks for listening. (music)

Chris Erwin:

The Come Up is written and hosted by me, Chris Erwin, and is a production of RockWater Industries. Please rate and review this show on Apple Podcasts and remember to subscribe wherever you listen to our show. And if you really dig us, feel free to forward The Come Up to a friend. 

You can sign up for our company newsletter at wearerockwater.com/newsletter. And you can follow us on Twitter @tcupod. 

The Come Up is engineered by Daniel Tureck. Music is by Devon Bryant, logo and branding is by Kevin Zazzali. And special thanks to Andrew Cohen and Mike Booth from the RockWater team.

Kevin Gould is the founder and CEO of Kombo Ventures. Many people say they’re the bridge between Hollywood and Silicon Valley, but Kevin’s the real deal. We discuss why he outsourced his script coverage as a young talent agent, when he liquidated his IRA to start angel investing, how "sliding into DMs" helped him launch 3 beauty brands with $75 million in sales, and how I misjudged Kevin when we first met.

Subscribe to our newsletter. We explore the intersection of media, technology, and commerce: sign-up link

Learn more about our market research and executive advisory: RockWater website

Follow The Come Up on Twitter: @TCUpod

Email us: [email protected]

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EPISODE TRANSCRIPT:

Chris Erwin:

Hi. I'm Chris Erwin. Welcome to The Come Up. A podcast that interviews entrepreneurs and leaders.

Kevin Gould:

I did two things. One was I played credit card arbitrage. The second was I think I had forgot what I had in my Roth IRA at the time and I cleared the Roth IRA account and cleared it out, and then took that money and invested in startups.

Chris Erwin:

This week's episode features Kevin Gould, the founder of Kombo Ventures and three direct to consumer beauty brands. Many people say they're the bridge between Hollywood and Silicon Valley, but Kevin's the real deal. He's also acutely aware of the value of his time. As a young talent agent in LA, Kevin actually outsourced his script coverage to his friends so he could fly up to the valley and meet with tech investors and CEOs.

Early success drove Kevin to launch his own digital agency, Kombo Ventures. A key player in the YouTube and influencer revolution. At the same time, Kevin also began angel investing through a $40,000 cash advance against his credit card, but in 2018, Kevin wanted to go even bigger in digital. He began sliding into the DMs of up-and-coming beauty execs and pitching new business ideas. With just six figures of startup capital, Kevin launched three beauty brands, and just 18 months later, those brands now generate 75 million in annual sales.

At the end of our interview, we talk about why Head of Live will soon be the hottest role in town. Getting called out on a Facebook earnings call by Sheryl Sandberg, and how I misjudged Kevin when we first met. All right. Let's get into it.

Chris Erwin:

All right. Kevin, let's rewind a bit. Why don't you tell me about where you grew up?

Kevin Gould:

I was born in Champaign, Illinois. Both my parents went to University of Illinois. I didn't live there for very long. I don't remember any of it. I was probably a year and a half old, and then I ended up moving to Greensboro, North Carolina where I spent pretty much my whole childhood through high school there, and so really call North Carolina home.

Chris Erwin:

Are your parents still in North Carolina today?

Kevin Gould:

No. My background on my parents. My dad is a professor of sports psychology. He also had a pretty extensive private consulting practice where he worked with a lot of athletes, and then my mom's a grief counselor. My dad ran the Sports Psychology Department at UNC Greensboro, which was a public college down in North Carolina. Then, after I graduated high school, he ended up going up to Michigan to Michigan State where he leads that department there still to this day. They're up in the cold now.

Chris Erwin:

Okay. Got it. What was it like growing up with a sports psychologist in the household? Were you like a big sports family? Were you a big sports fan yourself?

Kevin Gould:

Growing up I was a huge sports family. I think North Carolina is really known for basketball, so outside of Greensboro, you had Chapel Hill, you had Raleigh, you had Wake Forest, you had in that sort of like 90 mile radius. You had Carolina, Duke, NC State, Wake Forest. I also grew up in the era of Michael Jordan and the Bulls. I was a huge Bulls fan. It was really… Looking back it was really interesting having my dad as a sports psychologist.

Kevin Gould:

It's one of those things when you're a kid you don't fully appreciate it, right?

Chris Erwin:

Yeah.

Kevin Gould:

It was a little bit less of like necessarily my dad directly teaching me these things, but it was me picking up just from being around him and being around all these elite athletes the importance of positive thinking and mental toughness, because the really interesting thing and why sports psychologists are in business is primarily for individual sport athletes. He worked with a lot of tennis players, downhill skiers, race car drivers. If you're a car driver and you get in a serious wreck, that's in your head man and it really is hard to get that out of your head. There's a lot of mental work and mental toughness that goes into play.

Kevin Gould:

I think what ended up happening was sort of learning by osmosis and just being around all that, it really, to this day, I try to have a really positive mindset. Life in business as a roller coaster, right? So, really just being able to fight through that wall and having mental toughness is one of the key takeaways for me out of that.

Chris Erwin:

Yeah. I played some individual sports growing up like tennis and I remember how often I would get in my own head, and then reading a book called Inner Tennis, which was the psychology of the sport and just how powerful that thinking was. It's interesting that you highlight that.

Kevin Gould:

100%, and so my dad wrote the textbook for pretty much it's national use for sports psychology. I don't even remember going to the university and sitting in on the college classes and have to stop, I didn't understand. I was 8, 9, 10, right?

Chris Erwin:

Yeah.

Kevin Gould:

But the other half I really I think just picked up, again, just by listening and being present and being there. It was a super interesting experience.

Chris Erwin:

Was your mother in a similar field?

Kevin Gould:

They're both in the field of helping people. My dad was in the field of education. My mom was a grief counselor and she runs a non-profit still to this day. Quick kind of back story how that came to be. I had an older sister who actually died from a really rare metabolic deficiency before I was born, so I never had a chance to meet her, but for my mom at the time she really became like a pioneer of finding out more information about these metabolic deficiencies and helping educate other parents who maybe either lost loved ones to these or had children with these deficiencies and what was interesting is…

Kevin Gould:

Never really talked about this before. So, I've had this deficiency my whole life. I have to take medicine every day. I'm completely fine. I honestly don't even really think about it that much, but it is something that if left untreated is super serious. My mom really dove into helping other parents, particularly parents who've lost loved ones through this certain set of metabolic disorders. I think both of them were really, really loved to help other people. Again, my dad through the education lens and my mom's through sort of the grief support and consulting lens.

Chris Erwin:

Look, we're going to talk a lot about the many different businesses that you founded, but I just have to ask knowing about this condition. You said that you don't think about it often, but if you do take medicine for it every day, does that also cause you to think about your mortality and each moment counts and it's why you've maybe built so fast so early in your career? Have you ever thought about that?

Kevin Gould:

That's an interesting perspective and take on it I think. Look, I take medicine like three to four times a day and it's so ingrained in me, because I haven't known anything different. So, if you've been doing something your entire life, I don't know anything different than that. We can get into my drive and I think what drives me. I think maybe there's subconsciously some element to that. I don't know how much it plays in, but I mean, look, I think as we get older too, you obviously think about like what's important in life, what are you doing? What's your purpose?

Kevin Gould:

I think that could for sure have some play in it, but it definitely I don't think was the driving force for what drives me, but I think that's a really interesting take and perspective. I think there's some element of that that probably subconsciously comes into play.

Chris Erwin:

Yeah. All right. Well, let's talk about some other seeds of entrepreneurship in your early life. Did you know from early on that you wanted to build companies for a living or any other examples of skill sets that you're working on to help make you the entrepreneur you are today?

Kevin Gould:

I knew I wanted to be entrepreneurial. I just didn't know, one, how to go about it, where to start, what to do. We grew up sort of right around when the internet was starting to come up, but there wasn't YouTube, there wasn't a lot of information and education out there and people to look up to. Again, my parents were educators so they weren't necessarily in business.

Kevin Gould:

Then, I just didn't really have a lot of mentors when I was younger that I could look up to in North Carolina from a business perspective, but I feel like I just naturally gravitated towards… I was that kid that was the hustler that was always trying to start a side business. I have this memory that comes to mind. I was a swimmer growing up and the South and North Carolina, the community swim club over the summer are big things, and every summer there was this organization, it's called Swim for Cancer.

Kevin Gould:

The whole premise of Swim for Cancer was you would go raise money in exchange for swimming laps for cancer. The contribution of the young swimmer was go around the neighborhood, raise money, and then you'd swim a certain number of laps in honor of this organization. What it did at the time was I really was thinking back, I developed a lot of my sales skills through this, because I had to, middle of the summer, it's like a 100 degrees, humid in North Carolina, and I'm going around the neighborhood and I really had to figure out what my pitch was, right? Even though it was a non-profit, I was like 8, 9, 10 years old, I'm like, "How am I going to convince these people to give me money for this non-profit?"

Kevin Gould:

I remember going up to the doors like, "Hey, Mrs. Johnson this is Kevin. I'm swimming for Swim for Cancer, would you like to sponsor me?" Just through that, through knocking on 200, 300 doors over the summer, I started to sort of refine my pitch based on what was working and not working. Again, I didn't think that much into it at the time when I was at 8, or 9, or 10, but it was a really great learning experience that just translated to people skills later on in life, because I had to constantly adapt to the moment and every person was different.

Kevin Gould:

Mrs. Johnson was different than Mr. Jones who was the hard-ass guy, I'll be like, "How am I going to convince this guy to give me money for the non-profit? He barely wants to open the door." Then, at the end of the summer, you raise all this money, you swim all the laps, they have these awards, and then this is where I kind of learned in life like, "Look, everything in life isn't fair." Because I was like, "Man, I busted my ass all summer. I raised…" I don't know, like 2000 bucks or something from everyone in the neighborhood. I was like, "Yeah. I'm going to be the number one raiser in the city."

Kevin Gould:

I remember they called up the awards and they're like, "Oh, in second place is Kevin Gould with 2000 bucks." I was like, "Wait. Who could beat me?" Then, this one girl got $5000 flat and it was the check from the rich grandfather. I remember thinking, I was like, "Damn." Look, good for her, but I was like life isn't fair. It was a good… That whole experience was a great learning lesson, and then just throughout life I ended up working at that community pool.

Kevin Gould:

First started when I was 14 at the snack bar. That was a sales role, and then I became a lifeguard. You had to have a lot of people skills as a lifeguard, so I was always sort of training and not even knowing I was training for what I was doing today through all those things when I was a kid.

Chris Erwin:

I loved the story about raising money for cancer through the swim marathon. I also did a similar thing where I grew up in the Jersey Shore. In addition, I was also a boy scout and we used to sell Christmas, restoring Christmas. I remember I would take my bike out and go down these different driveways, knock on a random person's door in my town and sell them on a wreath and try and get money from them.

Chris Erwin:

It was like in the moment you feel awkward, you don't feel any confidence, but you start to develop those reps over time and you get better at it. Then, as you get older like sales is everything. It's not about just getting money from a client, it's about raising investor capital, getting your team excited, recruiting incredible team members to help build the vision that you have, getting buy-in from your friends and family, all the above, so what cool training you had early on.

Kevin Gould:

Yeah. It was amazing. To your point, every situation in person is different, right? You sort of have to in life and in business, you have to be able to adapt very quickly to the person and to the situation and everyone responds differently. For me, looking back that was amazing. I think that gave me an amazing head start and I didn't even know it at what I was doing at the time.

Chris Erwin:

Yeah. All right. Now, let's start to fast forward a bit. You go to UNC Wilmington, while you were there, was that a meaningful point in your life? Did you learn a lot or was it just a rapid stepping stone?

Kevin Gould:

When I was in high school I'd say I was an average to above average student. There was a lot of things that I was disinterested in and I'd always sort of asked my parents, "What am I learning this…" I was like, "Why am I learning this? I can't apply this to my real life?"

Kevin Gould:

There was always a little bit of that like, "What's the point of school because I don't think this is going to help me in the future?" I think that perspective was half right half wrong. I think I was a 16, 17-year-old kid just like stuck in school and there were a lot of elements that were helpful, but also, for me, there weren't a lot of things that I felt like were helpful for what I wanted to do.

Kevin Gould:

Anyways, I got into a couple of schools in North Carolina. I don't think I got into Chapel. I can't even remember. I don't think I got into Chapel Hill. I didn't have… Our high school super competitive, didn't have good enough grades. Got into UNC Wilmington, which is a pretty good school. I mean for me, what was important was on the beach. I was like, "All right." Greensboro. I'm going to what I thought was the coolest place in North Carolina, which is Wilmington and Wrightsville Beach, and got down there.

Kevin Gould:

I spent three and a half years there. I graduated a semester early, because I got AP credits. I studied business. I think it was marketing with I think a minor in entrepreneurship and leadership studies. But, again, college I think can lay the foundation, but teaching entrepreneurship is a really hard thing to do and learning entrepreneurship through a book or a class or case studies can maybe you can learn a few things, but really entrepreneurship you just have to jump in and go.

Kevin Gould:

I think looking back elements of it were helpful, elements of it probably weren't necessarily helpful, but at the time there wasn't an option like there is today for an 18-year-old where if I was 18 today, for me, personally, I probably wouldn't have went to college, but there wasn't any other option back then. It was still like you better go to college and you need a college degree to get a job, and so I had to go. It wasn't really like an option not to go.

Chris Erwin:

Yeah. I totally agree that that is changing. It used to be, as you said, if you can afford to go to college and you get in, you go to school and that's just what you do right after you get out of high school, but nowadays there's a lot more options. I think people are more open-minded and they don't want to incur the ridiculous student debt. So, questions are, do you take a gap year? Do you travel? Do you go work somewhere full-time, and then go enroll in school with more focus or do you not go to school and maybe do a trade school or learn how to program?

Chris Erwin:

I think that is very empowering to our new workforce. I agree that for certain people even if you have access to college, it's just… Yeah. It doesn't make sense.

Kevin Gould:

What's amazing now is there's the power of choice and the power of information that wasn't necessarily there back then for everyone. I think young people have incredible opportunities now and there's still things… If you want to be a doctor, you have to go to school. Specialized things, there's no way around it, but I think for someone who wants to be into business, luckily, there's a lot more flexibility now and you've got a lot more options.

Chris Erwin:

Speaking of business, after UNC Wilmington you head to LA. Your first job is at talent agency WME, but you were in LA for about a year and a half or so before you started your full-time role there. What were you up to?

Kevin Gould:

Yeah. Actually, after I graduated, so I graduated in the winter. It was a semester early, so I didn't get out to LA for a few months after that. I had to kind of get my bearings, get everything together, and then I drove out, and then there was a little, maybe a little under a year and a half period where I honestly, man, I was right out of college, I was 21, didn't know what I wanted to do.

Kevin Gould:

I was in college, so I worked at… I had a bunch of odd jobs. I worked at the Student Rec Center, then I became a certified personal trainer. I thought I wanted to start my own personal training business for a while. I was like, "Okay. This is something like I could be an entrepreneur, do something at the time, which I thought I loved." Then, I moved to LA and I kind of had odd jobs for a while.

Kevin Gould:

I was personal training. I ended up personal training a lot of people in the entertainment business. I got a lot of referrals, some really high level working actors.

Chris Erwin:

How does that happen? You show up in LA, you have an East Coast network, and all of a sudden you're training people in entertainment. How does that start?

Kevin Gould:

I knew a couple people out in LA at the time, and I was always good at sort of connecting. I think it Myspace at the time. I was trying to just connect with people. I knew a couple people out here, and then it kind of like was anything, it was just… I think I was pretty good with people. I was great at getting referrals and kind of built like… It was a very short period of time, but a small book of business for myself.

Kevin Gould:

I mean, dude, I got a real estate license. I was all over the place. I was like, "I'm going to be a real estate agent to the stars. I'm going to…" I just didn't know what direction I wanted to go in, and then I sort of started reading up on the talent agencies, and then someone at the time, on the client side connected me, and so got into WME probably 15 months after I got out here. It was such an experience, man. There is nothing like going into one of the big talent agencies, and really at the time it was… It still is. It's WME and CAA, right?

Kevin Gould:

Going in to the mail room where you do anything that they say. It was like a crazy experience, man. I remember you get in the mail room, there's a class of 10 other people that start the same week as you, and so you kind of form this bond with those 10 people that are in the class and everyone's kind of trying to size each other up. It's super competitive, but you have to do anything that the agents say.

Kevin Gould:

You're not even an assistant, you're not an assistant yet, you're getting called up by an agent, and they're like, "Hey, I need you to go get me a coffee, make sure it's like seven scoops of this. Don't do six. Make sure you stir it. If it's not hot, I'm going to make you go back and get it." At the time, that's the worst job for me, because I don't even drink coffee. I'm literally trying to google like how different coffees are made. I wasn't that sophisticated. I wasn't drinking coffee at 21.

Kevin Gould:

You literally run errands for all these agents and you're delivering scripts to actors. You have to go deliver scripts. It was like a crazy, crazy experience, man.

Chris Erwin:

Yeah. When you started, you are signing up to be a yes man. People call you do whatever they need, the talent, the agents, what have you. Just within the first couple weeks, were you energized by that? Being like, "All right. I'm a yes man, but what a cool environment to work in," or was there a little bit of an itch saying, "I really want to have my own path here and this feels limiting?" What was going through your head?

Kevin Gould:

Yeah. There was definitely an element of, wow. The energy inside an agency is insane. Everyone's moving and shaking and there's information flow inside an agency that you don't get anywhere else, right? You sort of like get plopped into the agency and it's this hub of just information of everything that's going on in the entertainment world and you're like, "Whoa." You're seeing huge actors walk down the halls and you definitely… When you're a 22, 23-year-old, you jump in there, you're like, "Wow. This is really cool."

Kevin Gould:

At the same time I was already thinking, "Okay. How am I going to quickly get out of the mail room, become this and like the path to become an agent?" I was like, "I got to get out of doing this." How am I going to kind of make the jump to do something else?

Chris Erwin:

I think that you have mentioned that you started early work in the Digital Department and doing some of the verse like digital and influencer deals out there. What were you up to?

Kevin Gould:

Yeah. Slightly different though. At the time, there really wasn't that much of a Digital Department at WME. There was one person. I started on a traditional talent agent's desk. I was working with that at the time, all of the young Hollywood type… The CW actors of 10, 12 years ago, right? Those would be digital influencers now. At the time it was like the it people of young Hollywood, which is the stars of the CW or Twilight or whatever, or Glee or whatever it may be.

Kevin Gould:

Then, I jumped around to a couple different desks over the years, because you become an assistant, you work for an agent for a while, and then you sort of move up to different desks. I worked across the Talent Department, and then I worked across the Non-Scripted TV Department, which at the time was starting to do a lot more digital work. Then, there was literally a one-person Digital Department. I think maybe it added one more person when I was there.

Kevin Gould:

I wasn't in the Digital Department. I sort of started creating my own universe of what I thought was digital at the time just on my own. I think I was the worst assistant, because I was trying to figure out how do I do the least amount of work I can as an assistant and get by and do a great job for the agent, and then sort of run my side business on the side where I just started naturally gravitating towards what was going on in Silicon Valley.

Kevin Gould:

Every free minute I had I was reading TechCrunch. I was reading all the Silicon Valley blogs at the time about what was happening there and I started to see-

Chris Erwin:

This was around 2010, 2012?

Kevin Gould:

It's like 2011, 2012. The first year I was really just in it just learning the talent agency side of the business and I also learned the things I didn't like to do. When you're an assistant in the Talent Department, you're responsible for every couple of weeks you have to cover a script. The agencies get tons of submissions. The agents aren't going to read it, the assistants have to read it. You get assigned a script to read. I started reading these and I had to write a summary and I'm like, "This sucks, man. I don't want to read scripts and summarize a script." I actually started paying people on the side 50 bucks to do it for me because-

Chris Erwin:

You're arbitraging time.

Kevin Gould:

I was arbitraging time. I was like, "I hate doing this. It's not…" That made me really realize, I don't really want to be a traditional talent agent working with actors, because I don't like reading scripts. It's fun to watch movies, wasn't fun to watch scripts. Then, after the first year that's really when I started to get really intrigued by the digital space, and which then sort of led me to after just reading about it for a while, seeing some of these really cool companies popping up. When I'm reading TechCrunch, they raised a little bit of money, and I'm like, "Man, I feel like if they had some entertainment connections, I could be helpful to them."

Kevin Gould:

I just started emailing these like cold emailing from the WME email address. "Hey, this is Kevin, I work at WME. I'd love to meet with you guys. I think I could be helpful on the entertainment side." Then, on Fridays, I'd kind of fly up once or twice a month to Silicon Valley and just take meetings with these people.

Chris Erwin:

You're meeting with investors and CEOs, founders of companies?

Kevin Gould:

This was what I found interesting. I found a gap where people being young, people thought I had something of value that they didn't. I couldn't do shit for anyone in the talent agency. Like, "What am I going to do for an agent that's been there 20 years?" I didn't have a skill set that they didn't have. I would have to try to be them, right?

Chris Erwin:

Yeah.

Kevin Gould:

But I saw this gap where all of these founders and even these VC funds, they had no clue how the entertainment business worked. I was like, "Wow. I can be that bridge that sort of sits between both worlds." I really spent a year just getting to know the space, flying up, meeting with people, building the Rolodex, plugging them into relationships and not even asking for anything just to sort of build some relationships.

Chris Erwin:

Yeah. Do you remember some of these companies? Who are some of your first Silicon Valley clients?

Kevin Gould:

Well, maybe I'll cut to kind of how it officially kind of came to be, because before it was… I remember at the time I was sort of signing clients on the side. She's a really good friend of mine, Jesse Draper. Do you know Jesse? She runs a VC fund down in LA.

Chris Erwin:

I think I met her when I first moved to LA in 2012. I don't remember she was like on the cap table for big frame, but she was like around that whole world.

Kevin Gould:

Yeah. We put her with Big Frame. I signed her on the side as a client and I was like, "Okay. We're going to build out a huge digital show for her." She was plugged into Silicon Valley. She was one of my first clients while I was at WME that I like took on and worked with from a, not a company necessarily, but a person and her and I are still really great, great friends to this day, but then there were just a lot-

Chris Erwin:

Kevin, to be clear. The business was not through WME, this was through you individually?

Kevin Gould:

No. Not yet. Jesse was through WME and I signed her, I was at WME, and the agent that I was working for at the time was really supportive, and all the other businesses I was helping at the time, because I was at WME, it was really informal. I wasn't taking money from them. I was just doing it to learn the space. What it allowed me to do was refine my understanding of what made a good company, what made a good founder.

Kevin Gould:

I mean in the beginning my instinct wasn't as good. I was going after companies that couldn't get to scale, maybe didn't have the right founder, maybe there was a ton of competition in the space, and then at the time, I was working for an agent and the way the agency is laid out is you've got all the agent offices, and then there's a huge row of just like… You've been in the agency. There's a huge row of assistant desks and assistants all sit next to each other.

Kevin Gould:

I was sitting next to this guy, smart guy, worked at Goldman, gave up everything to come to the agency, and then he was working for Charles King at the time, who now runs Macro. We would sit next to each other and just talk about the tech space and we sort of share the same passion. We ended up leaving together and we started, what was at the time, a company called Startup Agency, which the whole idea was Startup Agency was going to bridge Silicon Valley and the entertainment side of the business.

Kevin Gould:

One of my first clients that we signed was, again, someone who's become a really great friend to this day. It was a company called Gift at the time, which the whole premise of Gift was a digital gift card app that could buy, send, sell, receive digital gift cards and I met CJ, the founder… I went to TechCrunch Disrupt, the big conference. I saw him present on stage. I went up and said, "Hey, man, I've got this company called Startup Agency…"

Chris Erwin:

You just approached him cold?

Kevin Gould:

Just approached him cold. He kind of looked at me like, "Who's this guy?" Kind of blew me off. I said, "Give me your card." I gave him my card. He gave me his card, and then the next week I called him, he was still apprehensive. I got on the phone. I was like, "Look, I can really help you out. If you could get to anyone in the entertainment business, who would it be?"

Kevin Gould:

He said, at the time, Giuliana Rancic was a new mom on E. Perfect for what they were trying to do as an ambassador for their business. I said, "Okay. Give me a couple days." I came back a couple days later. I said, "Hey, I got a call set up with Giuliana's manager and her team and Giuliana. Let's put a partnership together." Two weeks later, she came on as like a big face and an ambassador to the brand, and then we did a ton of other things for Gift along the way.

Kevin Gould:

That was one of the first clients, and then so Tim and I is still a good friend. He ultimately wanted to go more in depth with us, a single company, and that's when sort of Startup Agency kind of pivoted. I rebranded and kind of became an element of what Kombo Ventures is today.

Chris Erwin:

You go full into Startup Agency I think in 2012, right?

Kevin Gould:

Yeah. I think 2012. Yeah. It's the end of 2012. Right around there.

Chris Erwin:

Okay.

Kevin Gould:

It's funny because I think some people have very linear paths. They were like here for three years and here for two and here for a year. Mine was very like it all sort of blended together. I was at WME and I was trying to sign these people on the side and have my own business, and then I sort of moved into Startup Agency, and then that sort of morphed into Kombo.

Kevin Gould:

There was this constant just evolution of what I was doing as opposed to a hard rigid like, "Here for this year, two years, three years." It just sort of morphed and evolved over time.

Chris Erwin:

Yeah. Kind of like the image that's coming to mind is a plant or a tree that's growing, and then there are these branch offshoots that might be like, "Oh, I'm incubating this idea. See where that goes. Maybe it grows maybe it doesn't." Then, there's this other offshoot, and then it becomes like a through line where the core of your career and all these different things build upon that and reinforce it, but then can take you serendipitously in different directions. I feel like that's what you did.

Kevin Gould:

Life is all about serendipity and that's a good analogy you made about the plants and different paths. Then, it still ends up all working up to the same place, but it kind of diverges here and there, but it all ultimately, even if you don't think it makes sense and at the moment it ends up making sense. That's life.

Chris Erwin:

Yeah. 100%. Startup Agency, and then I think that you take on a 10-pole client in Videogram and Cinemacraft for a couple years, but Kombo, what is now known as Kombo Ventures, which is a hybrid talent management, IP, incubation studio, digital agency, consumer brand launcher, that also really kind of takes off at the same time.

Kevin Gould:

So at the time there's this company called Cinemacraft. They had a product called Videogram, really interesting sort of early video product that they had an algorithm that allowed basically videos to be spliced and diced algorithmically to pull out the most key points of the video. It was mostly like a B2B sales play where you sell into studios and networks and content providers. It was part of Turner at the time had this thing called Turner Media Camp where Turner was funding startups, and so that as a client at the time, I got super involved.

Kevin Gould:

I was really part of like the founding member of the team there. I wasn't the founder by any means, but was on the founding team and that was a great experience to get a little bit more operational in one company where I still had other clients at the time, and sort of I ultimately realized I wanted to at that time be involved across multiple clients, and really build out Kombo and the whole model of Kombo sort of shifted into a real agency where I was looking for…

Kevin Gould:

The thesis was go find late seeds, series A, sometimes series B companies that didn't have someone internally that had my relationships Rolodex, know-how of the entertainment business. Go to them and have a sort of hybrid model where I would take a retainer, because I needed to get paid, take sweat equity. I didn't have a formal finance background, so what that allowed me to do was learn all about cap tables, all about financing, learning by just osmosis of just being around it.

Kevin Gould:

Then, ultimately, what I realized, it's like, "Wait a second. These companies that I'm taking equity in…" Because I'm super particular and I wouldn't just work with any company, they all have zero trouble raising money from top tier funds. I was seeing I had a firsthand view of how well the company was doing, because I was very integrated with the companies. I started negotiating to let me invest in the last round of funding, because at the time, I was cutting small angel checks of what was 10k or 15k or 20k to them, at the time I was taking that consulting money, and then dumping it back in.

Kevin Gould:

It became this really interesting model where I had a couple wins that really worked. I had some that obviously went to zero, but the ones that worked, worked well and most importantly what it allowed me to do was I basically got to make money and get a really good generalist view of how lots of different companies are run, how lots of different founders work, because they all work different. It was just amazing at that time of my life to be able to do that.

Chris Erwin:

Well, and I have to say, so a few points. One, that rubric you talked about, flying up to Silicon Valley, starting to get a sense of what companies were meaningful that you felt are worth betting on versus not. You started to create that filter that you likely applied now at Kombo. So increasing your likelihood of success, better return on your time. Second what I'm hearing is that early stage companies, seed series A, getting them to pay you a monthly retainer as an advisor is not easy.

Chris Erwin:

I run an advisory business myself. I specifically target later stage companies that have cash wherewithal. So impressive that you're able to get them to spend money on you, but then also they want results often, and so you must have been delivering to have maintained those relationships.

Kevin Gould:

So very, very good point. It's really hard to get startups to pay you money when they're obviously very cash conscious, particularly if they're that series A stage where paying a $5000 retainer a month or whatever it is that I was charging back then was hard to come by. What I did was I always delivered before I asked for anything. I think that's a good thing to do in just life, whether you're someone that's trying to come in a company, whatever it may be.

Kevin Gould:

Always deliver a little bit, show that you can drive results, and then it makes it much easier to ask for something after you've already done that. At the time, I was like young coming out of WME, it's not like Kombo was kind of I guess what it is today where it's a little bit more established and I had a little bit more of a reputation. I didn't really have much of a reputation. The only way to do that was to deliver before I asked for anything, and some people would say, "Oh, well, that's a waste your time. Well, what happens if they don't compensate you or whatever?"

Kevin Gould:

I look at it a completely opposite way. It always… At least, for me, it always ended up working out. Even if I didn't end up working with them, I still know those people to this day. I can call on a favor. I've gained a relationship, whatever it may be. Maybe it took me 5 to 10 hours of work to put in to try to gain the client, but that's the only way I could get them was to deliver, and then ask later.

Chris Erwin:

Yeah. You were looking at it from a long-term point of view, lifetime value the customer. So, by doing the work up front, even if you don't get paid for that say like 5 to 10 hours, that could be a customer for the next 10 to 20 years of your life. They can be paying you cash retainer fees. They give you access to their cap table. They refer you to other advisory clients, because they like you. You're able to make other angel investments.

Chris Erwin:

It's incredibly valuable to put the work in, which also filters if a company appreciates that, that's someone that you want to work with. You feel them out over time. It's a two-way interview.

Kevin Gould:

100%, and life is a series of compounding relationships. You put in on that work, you help people out, you do good by people, and all of that over time starts to compound to I think kind of what it is today where I feel like I know a pretty good amount of people. I've put in a lot of favors for people, if I ever need to call in a favor, I probably can. It's just this like network effect that continues to expand over time.

Kevin Gould:

I try to encourage all these young people that are trying to get in it for the quick money. It's just take a step back and just think a little bit about the long-term and there's other things other than like the quick hit that are going to be ultimately a lot more meaningful and beneficial to you long-term.

Chris Erwin:

Something else I just have to quickly touch on here. I think you mentioned this when we last spoke, but credit card arbitrage with your angel investments. So, you are making these small cash retainers as far from life-changing money, building a small business, so probably not a lot of extra cash going around, but you're putting money back into your clients, so you're like not diversified. If a client goes away, you lose your angel investment and you lose that retainer, but you're even tripling down in a way because you were going into credit card debt so you can put more cash into these companies, is that right?

Kevin Gould:

I'll even go one step beyond that. I remembered another thing I did, which was crazy. One was I thought, "Okay. I've got all these access to these incredible deals." For whatever reason in my head, I've never had that risk alarm bell. For me, anything I do I don't think is a risk, because I feel like I've assessed the risk and I feel like if I'm doing it, it's not a risk. I ultimately know there is a risk, but I don't know, my brain has always operated a little bit differently in terms of risk profile.

Kevin Gould:

I said, "Man, I've got $40,000 of a line of credit on one of my cards and I'm looking at the interest rate, I'm like, "Okay. What happens if I basically go max out this card and basically play interest rate arbitrage where if I can get into a couple of companies there's the…" The downside of it might go under, but there's the upside of, "Look, maybe it's a 15% interest rate a year, but if this thing can 3x, 4x, 5x, 10x, whatever it may be, that's a pretty good bet."

Kevin Gould:

I did two things. One was I played credit card arbitrage. The second was I think I had… I forgot what I had in my Roth IRA at the time and I cleared the Roth IRA account, and cleared it out, and then took that money and invested it in startups.

Chris Erwin:

Wow.

Kevin Gould:

For anyone listening, I would never recommend doing that. It's not a strategy I would recommend, but I don't know. It made sense to me. It's hard to explain, because it rationally doesn't make a lot of sense and I'm a pretty grounded rational person a lot of ways, but I'm also willing to take a lot of risk. I don't know, that made sense to me.

Chris Erwin:

Yeah. I think liquidating an IRA, I think there's like a 10% penalty on top of that too.

Kevin Gould:

Yeah. I had to pay the penalty to liquidate it too. I had to pull out the cash, you're not earning interest on the money you're gaining, you're also paying the pre-liquidation penalty, but I got enough capital between the credit card arbitrage, the IRA, and the incoming revenue that I had coming in on the agency side of the business, because I was just basically paying my rent. I'm pretty simple. I wear like basic hoodies, t-shirt. I didn't buy a lot of fancy stuff and that's how I did it.

Chris Erwin:

In these early days, was there ever a point though where there was like a cash crunch? Every founder, and like this is me like every week, "Oh, are we going to make payroll this month? Oh, here's all the things that could go wrong and put us out of business." But you need to think optimistically. Were you ever down on your business?

Kevin Gould:

Luckily, I kept it really lean at the time. It was more about like, "Am I going to eat or not going to eat?" I always had enough to… Again, I feel like one of my natural skill sets was sales, so there was always enough of a client base to cover. We'll talk about I guess in a little bit the brand side of things, because when you're running a brand, a larger brand there's a lot of moving pieces on cash flow. But because I kept it lean, I was generally okay, but I had to really not live beyond my means, and also always be on the hunt for new clients and new business development.

Kevin Gould:

I definitely wasn't swimming in cash, because, again, I was taking lower retainers in exchange for these equity stakes, and then when there were some cash crunches, serendipitously, a company exits and I get a payout or I close a bit deal. I don't know, man. It always ended up somehow writing itself and, yeah, it was crazy.

Chris Erwin:

Yeah. I think that's the success formula. It's hard work having some diversified bets, and then a bit of luck where things just work out, and resilience. In those tough times not hanging up the towel. Be like, "No. We can get through this." Because all startups they just need a little bit of time. With time, the worst that can happen is you go to zero. The best is like the sky is limitless.

Kevin Gould:

That's exactly the way I think about it. The worst that can happen is it goes to zero, and ultimately, you learn from it and you start over. I know that sounds very simplified, and so a lot of people I think going to zero is that's obviously terrible, but for me, I'm like, "All right. I'll just from scratch and rebuild." That's kind of how I always thought about is the worst that happens is I learned a lesson and I got to rebuild.

Chris Erwin:

I like how Jocko Willink describes it who's former special forces and he's now an incredible executive and leadership coach and has his own podcast and much more. He's done the scenario. He goes through his worst case scenario planning, which is like, "Okay. If I'm really making pennies, then I will have a blanket on a concrete floor and I will eat beans out of a can." He's like, "That's not that bad." He's like, "I've had worse in combat scenarios."

Chris Erwin:

It's like when it's uncertain of how bad it can get, you freak yourself out, but when you actually get there logically, you're like, "Oh, I can do that for a few months. I can do that for a year. Sure."

Kevin Gould:

100%, and obviously, you don't want to do it, but you'll ultimately be okay. Then, it's just a matter of being resilient and getting yourself out of it and coming up with the next thing. Ultimately, that's like all business. If businesses can't get creative and continually be ahead of what's next, they're ultimately going to find themselves in that position anyway, so you have to constantly be coming up with new things to reinvent yourself, get creative. I don't know. That's how I think about it.

Chris Erwin:

Yeah. Cool. All right, Kevin, let's talk about how Kombo Ventures has evolved over the past couple of years. You've had some very exciting developments in your company where in addition to all of your agency management, IP studio work, you've now launched three very fast growing direct to consumer brands. Let's start out, what was the catalyst to evolve Kombo Ventures, and then specifically get into beauty products?

Kevin Gould:

Yeah. A couple catalysts, and maybe I'll cut back slightly, and then loop back into how this all kind of came to be. After running the agency side of the business for a few years, I was seeing the rise of influencers and big digital influencers, content creators, YouTubers, and thought there was a gap in the market where a lot of these talent needed to think about their brand as a real scalable business.

Kevin Gould:

I ended up basically starting another part of the agency where more of a management company where we were just managing and signing digital YouTube creators, big talent, and so for a while it was a split of still working with companies and doing all of the advisory agency services we were talking about, which is one part of the business. Then, the other part was managing these talent.

Kevin Gould:

On the beauty side, one company probably five, six years ago I got really deep with as an investor. Sort of fell on hard times now with the events, business and COVID and everything was BeautyCon, and through BeautyCon, I really saw, one, the influence that influencers have on the beauty business. Two, the scale of beauty businesses and how much they can scale. I think they were always very forward thinking from an e-commerce perspective.

Kevin Gould:

Then, the other we're seeing through the influencers that we were managing was like just even at a very basic level when they had their own merch business, the amount of scale that one influencer could get from moving merch. Which then led me to, "Look, I really want to start building my own brands." I'd say in summer of 2018, I had known Sharon Pak and Jordynn Wynn for a while. They were basically like the first two employees over at ColourPop Cosmetics, big cosmetics company.

Kevin Gould:

I slid in their DMs on Instagram. I DM both of them together and I said, "Hey, what are you guys up to? I'd love to catch up." I schlep over to Calabasas because they were working out of Oxnard, we met in the middle. I sat down. I was like, "Look, if you guys could start a brand and what space would it be?" We sort of just started talking and they were like, "Look, we think the hair space is a really interesting space. We don't think it's been innovated." You're like, "Color cosmetics has. There's a lot of legacy players, but they're not great at social content creative like sort of influencers."

Kevin Gould:

I kind of went back that night and did a bunch of research. I came back a day later and I said, "Hey, here's all the research on the space. Let's do this." They're like, "Whoa. Are you serious?" I was like, "Yeah. Let's do it."

Chris Erwin:

You were like jazzed up immediately?

Kevin Gould:

I was jazzed up immediately. I was looking for co-founders that… It's important to have co-founders that can do things you can't and vice versa, right?

Chris Erwin:

Yeah.

Kevin Gould:

I think their core expertise was social, creative, community building online, and so we partnered up and the brand launched. It was a soft launch, but it launched in October of 2018. That was the first brand.

Chris Erwin:

This is called Insert Name Here.

Kevin Gould:

Insert Name Here, INH Hair for short. When we started, it was primarily actual hair. Like Ariana Grande style ponytails, like that ponytail she always wears, hair extensions, wigs, lots of hair products. It has since transitioned into overall hair business where we sell blow dryers, straighteners, hot tools. We have hair color now. It's expanded a lot. Then, cut to last year there were two other brands that I launched and co-founded.

Kevin Gould:

One was also in the beauty space called Glamnetic. It is in the women's eyelash space. I did that with my co-founder Anne McFerrin, who's incredible, and sort of similar in that she is incredible at social, creative content, community building. I think a real visionary from a product development perspective. We launched that. Then, the third brand was called Wakeheart, which I did… This was done a little bit differently.

Kevin Gould:

It was done with the Dolan twins who were two big YouTubers and digital influencers. It's a fragrance and scent brand, really aimed at like Gen Z and young Millennials. The through line is that with all these brands we're like, "Okay. Look, we need to get these things profitable within six months or less." That was like one goal we set. We're going to run these things lean. I wanted in the beginning a pretty large degree of autonomy. I didn't want to raise capital. So, self-funded the businesses-

Chris Erwin:

Jointly funded with your co-founders or were you just contributing capital?

Kevin Gould:

Different on each one. One of them I funded all of it. Two of them, I think we split some of it. Then, I was bringing… Mostly I was bringing the capital, and then I was bringing all the op side, everything on the operational side of the business. Then, I'd say I'm pretty strong on the marketing side as well, and so bringing a lot of that to the table and kind of cut to today. There's these three brands running, we still haven't taken on any capital for any of the brands. Man, there's like 90 something people across everything now.

Kevin Gould:

The brands grew really, really quickly. It obviously has been a very interesting year with COVID and how sort of everything accelerated from an e-commerce perspective. But it's been a lot of fun.

Chris Erwin:

Yeah. Going back to meeting the co-founders, how did you sell them on you? Because you show up… I think you kind of knew the ColourPop cosmetics team, but getting them to launch a business, change what they're doing, take on a bunch of risk, sign up for a lot of work. How did you get them excited about these ideas you had?

Kevin Gould:

You know what's funny is I feel like you'd have to ask Sharon and Jordynn, but they've kind of talked about it before. I think they like did… I don't know if they thought I was that serious at first, right? I was that serious. I literally sat down, and I said, "Hey, if you could launch anything, what should we launched?" Then, literally a week later we're meeting every weekend while they're still working like getting this thing strategized and planned and going.

Kevin Gould:

Yeah. I don't know. I think it was just an open honest conversation. I was like, "Look, we think there's a big opportunity here and let's take a shot at this and do it." I think to their credit too, I think they wanted to start… It was all serendipitous, right? They wanted to start their own business at the time and I think we all complimented each other in terms of the skill sets that we brought to the table, and so it just made sense.

Chris Erwin:

Then, you also said that you brought ops expertise to the table, but you don't have a background in launching CPG, e-commerce businesses, in fulfillment, developing relationships with manufacturers, designing packaging, so did you hire a team to help you figure that out or did you do it yourself?

Kevin Gould:

I've had my right hand guy, Lucas, who's been with me for a while. He's awesome. He also did not have a e-commerce op background. He had a banking background where he was at the Soros fund, and then kind of like do anything figure it out sort of mentality. I kind of just looked at the space and I was like, "We can figure this out." It's like anything, right? You put enough time into it and just dig in and be curious and ask a lot of questions. It's not rocket science.

Kevin Gould:

We're not building a biopharma company. It's not something completely out of my wheelhouse. I think by virtue of seeing a lot of companies being built over the years and sort of being close to the space, I knew enough as a generalist to be able to go in and figure it out, but you're right. Never cut a fulfillment center, put a fulfillment center deal together, never had to run the back end on the accounting side for an e-commerce business before, but you kind of just figure it out as you go.

Chris Erwin:

Just learn by doing.

Kevin Gould:

Learn by doing and the key is one thing with putting up your own money is you are very conscious of making sure you minimize mistakes, right?

Chris Erwin:

Yeah.

Kevin Gould:

For me, I'm like super high touch and heavily involved in each of the brands and still am to this day and just the key is, it's like, "How do you scale as quickly as possible to minimize the major mistakes you make?" It's okay to make mistakes and we want people to make mistakes because otherwise they're not moving quick enough and learning and growing things, but from a cash flow perspective going back to the cash flow piece, you need to make sure you don't make too many mission critical mistakes or you'll be out of business, particularly if you're self-funding your company.

Chris Erwin:

Speaking of the cash needed, how much capital did it take to actually just first launch these brands and get the first product out the door? Are we talking seven figures per brand, was it five to six figures of cash investment?

Kevin Gould:

I'd say minimum six figures on each brand, and then as they grow the biggest problem was trying to self-finance an e-commerce brand, if you're growing quickly is the inventory constraints. In the hair space, cost of inventory is really high. I had to put out for sure six figures initially to get the thing going. But, again, it seems crazy to do that, but to me at the time I felt like I calculated the risk. I felt like we're going to make this work and was willing to do it. It didn't seem like a… I don't know. I looked at it from all angles and I was like, "I feel like this makes sense and the worst that happens is I'm going to lose my money and I'm going to have to make it up again."

Kevin Gould:

But the real big challenge wasn't necessarily that I was fortunate to have had some successes with some of the previous exits where I made some money on some of the agency side of the business where I had that capital to deploy, but the most challenging piece comes, again, when you really scale it and you have to continue to deploy capital just to finance the inventory as you go, and you're too early to go to a bank.

Kevin Gould:

A bank's not going to finance a business that's been up and running for a year. You're almost even too early to go to a lot of the inventory financing solutions that are out in the market today. You kind of really need close to a year for them just to even get them interested, and so at points in time, I had to deploy a lot more than I wanted to.

Chris Erwin:

Personal capital.

Kevin Gould:

Personal capital. I had deployed overall a million dollars. I'm not going to break down exactly which one it went to, but across everything, a million dollars of capital, which was, one, way more than I expected. That's a lot of money. I'm not like loaded. That's a lot of money.

Kevin Gould:

I don't know. I believe in the brands. I believe in what we're doing. I believe in my co-founders. It wasn't like the businesses were losing money. That incremental dollar figure that has went up over time is getting plowed into inventory. It's not like we're a business like some of these other e-commerce businesses that got in trouble where they were just blowing money every month and they were losing money on the P&L. This was for financing growth.

Chris Erwin:

I like what you said about starting lean with the six-month timeline to prove it out and get profitable. I think what a lot of companies, particularly digital media companies did when I got into the whole game back in 2012 was here's a vision for a business model that we can enter, and then here's how we can make money, but a lot of it didn't come into fruition. Then, it required them to continually raise money from investors, and then a lot of money was lost. That wasn't the approach for you.

Kevin Gould:

Well, and I think there were, obviously, hindsight for all those guys or women. It's like 20/20 in terms of what went wrong. I think there was like guilty parties on both sides. I think you had entrepreneurs that were coming up with self-justified LTVs of customers, and then they're like, "Yeah. The LTV is a thousand dollars of our customer, therefore, we can spend 500 to acquire them." When there actually wasn't enough data to really understand, what was the LTV?

Kevin Gould:

Then, you've got investors pumping money into the space encouraging them and basically adding on to that narrative of, "Oh, yeah, yeah, grow, grow, grow, grow, grow." Then, when the growth wasn't there and the LTV didn't back out, the investors were like, "We're cutting our losses. We're not in." You had a bunch of these e-commerce businesses that just fundamentally should have been run a much different way.

Kevin Gould:

I think the space is now getting reset where there's a lot more e-commerce brands or Omni-channel brands that are being run a little bit more efficiently. I think just the investor base has gotten, has been pushing companies to do that a lot more, but I was like, "We should be able to run this lean." you know, then you got to put up the money for the inventory, you got to test, you got to be in the weeds.

Kevin Gould:

In the beginning, I always tell early founders of social driven e-com brands, we treated Instagram DM as a sales funnel, right? Anyone that followed us, we'd shoot them a personal DM like, "Hey, thanks for following us. Let us know if you have any questions. We're here for you." That was like warm… If you're in a B2B sales business, that was our version of prospecting new customers. We had warm leads of people that followed us and we were actually going in and DMing them, having conversations with our first few thousand people that followed us on social and actually drove real revenue from that.

Kevin Gould:

It was just a down and dirty kind of guerrilla marketing style way of getting new customers on not a lot of capital. Obviously, as you scale that doesn't work as you scale as much, right? But in the beginning when you're doing 10,000, 20,000 a month in sales, it was a really great outside the box marketing tool for us.

Chris Erwin:

Yeah. As they always say in the beginning do things that don't scale. You learn from those tests and experiments, and I also like hearing about the story that you didn't have a specific playbook to follow in the beginning. You kind of learned and made your own. It's crazy I think with the number of e-commerce companies that are out there and you have Shopify and WooCommerce that you would think, "Oh, here's the playbook, here's how you find the manufacturer, here's the margin that you need."

Chris Erwin:

There are best practices, but you still got to figure it out for yourself and each talent situation, each product situation, each team situation is uniquely different. You just got to start talking to people, trying things out, and taking your ego out of it. One thing I've learned from you because you've given me some advice for some of our clients is you can have clients with billion dollar top line licensing businesses, but you know what? Start out with a small experiment which is maybe just a thousand units and see what works, and then you could build upon that and that's the right way to do it.

Kevin Gould:

100%. It doesn't all have to come at once. Start small and prove it out, make sure it works, and build from there. I think your point too on ego and I think everyone as an entrepreneur always have to self…. They always have to self-check their ego. You, me, everyone to a degree has an ego and I think to be a founder or a CEO or someone that's leading a company, and I'm certainly guilty of this as well sometimes.

Kevin Gould:

It's like you have to check your ego, make sure you're an amazing listener, right? You have to listen to everything. You have to listen to your team members, your co-founders, your customers, right? Even though you might have a perspective that you think is right and it might ultimately be right, you still need to take in all the feedback and listen and make sure everyone has a voice. That's always something that you continually have to refine and work on as a founder.

Chris Erwin:

So fast forward, you launched these brands, three brands within the past couple of years and you had a big moment this year. I think on the recent Facebook earnings call, Sheryl Sandburg, I think the number two at Facebook. She calls out Glamnetic as a great example of a fast-growing small, medium-sized business that's using their advertising platform. This is like you hear Glamnetic and the founder's name on the earnings call. It's amazing. I think you guys posted a video of that. What did it feel like? Did you know in advance that was going to happen?

Kevin Gould:

We did. I wasn't sure it was a go until the night before. I heard it was going to happen, but I still thought, went listen in on their earnings call… On those earnings calls, things get cut out last minute. I was like, "Who knows if this is going to happen or not." It was a really cool moment, man. I mean I think like, "Look, you got to celebrate the wins." I think that was like… I had a drink that night with my co-founder, and the guys as well. That was really cool.

Kevin Gould:

The business was super young, it was really a little over a year old. We've been fortunate to scale very quickly and that was just a really cool moment. One of the biggest companies in the world and you're on their earnings call, but you know what? You take the night, you celebrate a little bit. You're like, "Wow. That was cool." Then, you get to work the next day and you just keep building.

Kevin Gould:

It was an amazing experience. It's something that I think always remember when you're like as an early moment of the end, but I don't know. It's also weird because the brands have scaled really quickly, but at the same time I still feel like they're in their infancy. I feel like we're just getting started and-

Chris Erwin:

Yeah. Let's put some numbers behind that. I think that you mentioned when these brands like I think last year, run rate across your three brand portfolio, call it around $1 to $2 million of top line revenue.

Kevin Gould:

A little bit more like four to five last year. This year collectively 75.

Chris Erwin:

75?

Kevin Gould:

Yeah.

Chris Erwin:

That's like 20x.

Kevin Gould:

Yeah. It's been insane, man. It's been… What's crazy is like, again, it's definitely growing a lot, but I still feel like we're that small startup that's just like hustling to make it happen and the key is we have, again, I've got amazing co-founders in each brand and amazing teams. We have a lot of really young people that love what they do. I think they're learning a lot in these brands. It's been an amazing experience for them. They also put in a lot of hard work though and everyone's really, really passionate about what they do.

Kevin Gould:

We've got awesome teams on each of the brands. I think we figured out the playbook and the playbook's always changing. It's constantly updating, but to run a really strong e-commerce brand today, you have to do a lot of things right. You have to obviously be with an amazing high quality product, that's number one. You don't get in the door and scale otherwise. Then, you have to be killer at… It's like the flywheel, social content, creative, influencer marketing, paid media, retention, email, SMS, a loyalty program.

Kevin Gould:

That whole flywheel has to be running in lockstep and in sync in order for the brands to scale, otherwise, what happens is if you only have two or three of those, the barrier to entry to start an e-com brand lower than ever, right?

Chris Erwin:

Yeah.

Kevin Gould:

Super easy to get a Shopify site up. Let's say you own a brand, then, it's fairly easy… I wouldn't say it's fairly easy, but it's easier to get a brand to seven figures in sales, right? It's become easier to do that, but still I don't want to discount that that's really still hard to do. Then, take a brand to eight figures in sales or mid-eight figures in sales, you have to have all of those things working right, and if they aren't, you're going to have gaps and holes and it's not going to get there.

Chris Erwin:

When you think about how you really take this brand portfolio at 75 million this year to going to 100, 200 plus million next year, what are the next big moves to make? Is it something else that you're adding to the flywheel? Is it, hey, now is the time where we really need more capital? We need a letter of credit or inventory, financing? What are the one or two key things you need to sort out?

Kevin Gould:

Man, I wish it was just one or two. I feel like there's so much to do. I think to take a step back too. So, each of the brands are treated as individual brands, right? I've got different co-founders on each brand and we look at… Well, I'm involved in all of them at the Kombo level, right? Each brand is looked at individually and has a completely… There's a lot of overlap and synergies, but a completely different strategy and I'm sitting with my co-founders in each brand and figuring out for that brand, in particular, what do we need to do to scale?

Kevin Gould:

Again, some things are similar across the board. We obviously want to improve on costs or efficiencies and that's a given as the business scales. Then, I think there's just other things, a big priority I think going into 2021 is retail, North America retail expansion. I think you're going to see probably two of the three brands in retail in a big way in 2021. I think we have to continue to bring on really smart people that can fill in gaps that we don't currently have.

Kevin Gould:

There's things like data, data and analytics where I think we're average. I think we can get better there. You kind of have to go through the company and take a real look and say, "What are we not the best at?" Find people that are way smarter than you and bring them into the team and let them really run. I tell everyone on the teams and try to emphasize this, everyone in a startup is their own entrepreneur and an entrepreneurial organization.

Kevin Gould:

If you were the customer service lead, you were running your own… The customer service lead at Glamnetic, she is running her own business inside a much bigger business, and to try to treat their whole funnel and what they're working on as if it was their own business that they're running. I think if everyone in the team can look at that in their own portion of their business responsible for, ultimately, you've built a really entrepreneurial organization that everyone gets excited about.

Chris Erwin:

Yeah. There will be independent thinking and people will solve problems on their own or with their team members. That's what you need and when you're moving quickly where like you said there's not a specific playbook. It's like you just need smarts and people that want to lean in and figure things out.

Kevin Gould:

The other thing I think as a leader you have to do is you cannot lead by fear. If you lead by fear you ultimately are not going to get any of the results that… You might get short-term results, right? But you're going to see a lot of turnover. You're going to see not a lot of innovation because people are afraid to make mistakes and to innovate, there's going to be mistakes made.

Kevin Gould:

I think you have to really empower and encourage everyone on the team and give them a lot of autonomy, minimize major mistakes, because major mistakes are not good, but you have to really empower the team, because a company is not built by one or two or three people, it's built by the collective group of everyone working together.

Chris Erwin:

Totally agree. Well put. Before moving on to rapid fire, I just have to ask you about… Because you brought up expansion through new retail channels, we've written a lot about live stream commerce, looking at the Chinese market. It was around 65 billion last year. This year was forecast to do around 130 billion, but I think it's coming in at like near 170, 180, and I know as digitally native brands that use, you also have social selling models. You sell through Facebook and Instagram shop and likely other avenues. Is live stream selling part of your strategy in the New Year or do you already do it?

Kevin Gould:

I'm obsessed with live commerce. I love the things you guys write on it. I consume all that content.

Chris Erwin:

Thank you.

Kevin Gould:

I'd say I spent the last six months to a year being constantly curious and reading everything about live commerce and just really figuring out where I think our brands can kind of play in that world. We've been experimenting with a lot of different things. It takes a really big effort by the team and there's not immediate results right now, right?

Kevin Gould:

I think anyone that's jumping into live commerce is building ultimately for the future, which, again, each brand is a little bit different, but I'd say the through line is that I think everyone is excited about the potential live commerce. It's going to be interesting to see how the platforms play out and where do you invest the time? There's also the other platforms that are not one of the major platforms that are… It's the networks, the pop shop lives. Everyone's sort of coming up with their own niche that they're going after.

Kevin Gould:

As a brand, you have to figure out where you're going to invest your time and where you're going to play. We're like in the middle of that right now, but I think for us, live commerce is a really big priority to invest in next year with maybe not a ton of short-term results, but a lot of long-term equity. The other thing I think that in two years the hottest role in town for a new job… It's like six years ago when it was like we needed a head of influencer relations, right? That was a really attractive role.

Kevin Gould:

I think there's going to be a lot of roles where companies are hiring ahead of live commerce. That's literally the title. It's just going to be a really… Who knows? I don't know if it'll take a year, if it'll take two years, if it will take three. We'll have to see what happens in the space, but I'm super excited about it, and to your point of how big it is in Asia. If some of that can be implemented here, it's going to be really cool.

Chris Erwin:

Yeah. That's a good take. Think of an analogy, right? When we used to advise creators at Big Frame and Awesomeness, they have so many different platforms that they could publish on. You could be on Facebook, on Instagram, on TikTok, on Snapchat, on YouTube, and it's really… Unless you have a fully built out team, it's hard to be everywhere and to be really effective, to program well, to interact with your audience, to do really great work.

Chris Erwin:

I like how you put it about commerce is there's many retail channels that we can be, but we have to focus on the ones that are the best fit for our business at this stage and that we're also just where we are well set up an advantage to perform. There's others that we want to be, but let's not just jump into it. Experiments make sense, and you guys will probably try some things out, but then navigating that world… Yes. We've looked at all different players. You have the big tech social incumbents.

Chris Erwin:

You got Amazon and Amazon Live. You got Facebook Live, Instagram Live, and they're commerce and shops. TikTok and Snapchat are doing live commerce, but then all the niche players like you said, Pop Shop, talkshoplive, Shop Network, so like what's best for you? It's a lot to navigate.

Kevin Gould:

It's crazy, man. It's exciting, because there's so much going on. I think the biggest challenge is going to be the amount of resources that brands do have to dedicate to it to get… There has to be a real incentive coming from the platforms to get the brands to do it. I think bigger big brands, they're going to be late to the game like they always are on stuff, because they just… They're not going to be able to move internally quick enough to like… They're going to talk about it for two years while they wait to see what happens and probably jump in.

Kevin Gould:

I think what happens though is that creates an amazing opportunity for brands like ours and other brands that can move quickly and understand how to navigate the space to dive in and be early. I always like to be early on things. You never want to be too early but it's great to be early. I'm psyched about it. I'm literally anytime you put some content on, I'm reading everything and just consuming a lot of information about it.

Chris Erwin:

Look, the new way to sell is digital, social, and with personality. You guys are very well set up for that. Before moving on to rapid fire, I'm just going to close out this segment with a bit of a kudos to you in a little anecdote.

Chris Erwin:

Kevin, I think I first met you within the first couple years of me moving to LA. I think this was around probably 2013, 2014. We were at a typical kind of Hollywood type party where it was like nighttime, lights, pool, patio, it's nice out. A mutual friend introduces us. I look at you and I'm like, "Here we go." You're saying you're an angel investor, you do these things. I'm like, "This is a young guy…" I don't want to say you came off slick, but you just had… You were doing interesting things.

Chris Erwin:

Good looking. I'm like, "Oh, this is just like a typical Hollywood set." I judged you, but as I've gotten to know you over the years, I've been so impressed with how smart, thoughtful, yet very gracious you are with your time and how humble you are. That you give me time and others around you your experience, your expertise to make this whole industry better. You very much have this positive sum approach, which really, really resonates. You're amazing. I love the work that you're doing. I want to give you a little shout out.

Kevin Gould:

I appreciate that a lot. It means a lot. I mean I feel the same way about you. I think we've probably known each other seven, eight years, and it's been amazing to see everything you've built as well. I really appreciate that compliment.

Chris Erwin:

Very welcome. All right, Kevin, moving into the rapid fire to close this out. I have six questions. The goal is to answer them quickly in one to two sentences or even one to two words. Do you understand the rules?

Kevin Gould:

I understand the rules. I have not looked at any of these beforehand, so maybe it'll take me more than a minute, but I'll try to be quick.

Chris Erwin:

All right. I'll hold you accountable. All right. Let's kick it off. Proudest life moment.

Kevin Gould:

Proudest life's moment. There's not one life moment that comes out. To me, I think it's a collective of everything. I think life is all about experiences. Whether that's experiences with my family, which one thing I'm working on is I'd love to spend more time with my family. Experiences in business, achievements. There's not one moment that sticks out where I'm like, "Wow. That's the proudest moment." It's a collective… It's all these serendipitous moments that come into play and you kind of look back and you're like, "Wow. That's incredible." It's not one moment for me. I hope that answers the question but it's life in general. It's the through line of just navigating life.

Chris Erwin:

Got it. What do you want to do less of in 2021?

Kevin Gould:

I want to do less of the things that I'm not necessarily the best at, but there's not anyone else to do it now. I think that's just a matter of as we continue to bring on people that are probably better than me at certain things, they're going to be able to thrive in those things. It's going to be able to pull me out of some things that I'm probably not as strong at, but I've had to do now, because there's no one else to do it. It will allow me to have more clear focus on the things that I think I can thrive at. I think ultimately doing less of the things I don't like to do is a good priority for next year.

Chris Erwin:

Yeah. Continuous arbitrage of your time and your passion.

Kevin Gould:

Man, not to get too off track. I gave up driving five years ago. I just take Uber full time, because it's the opportunity, cost of time, and it's the time arbitrage, right?

Chris Erwin:

Got it. What do you want to do more of in the New Year?

Kevin Gould:

I want to spend a little bit more time… We'll see if this happens. It's unfortunate because of COVID and we're far apart. I'd love to spend more time with my family who I have not got to see a lot of, and admittedly, I always throw myself into work, and so I need to prioritize that more. I would love to do more of that.

Chris Erwin:

What one to two things drive your success? Short answer.

Kevin Gould:

Yeah. For me, I think I like to prove things to myself. It's not like I have a chip on my shoulder in any way, maybe there is a little bit where I want to prove it to myself, but it's always trying to get better and prove that if I think I can do something, I really, really want to do it.

Kevin Gould:

The other thing that really drives me, there's two things. I love learning, and so I love being constantly curious and in the mix and knowing things… I love knowing things before everyone else. I want to be ahead of live commerce before everyone else. That's I love learning. I think the third thing is the interaction with team members and the joy that working with other people, the positive and negative dynamics that come with running a company, working with people, conflict resolution. That's fun to me and it really just drives me to try to get better.

Chris Erwin:

Advice for media and direct to consumer execs going into the New Yea.

Kevin Gould:

To continue to stay constantly curious on things and make sure you are always trying to be ahead and don't settle for what's working now, because what's working now might not work three months from now, and so you constantly have to be testing, iterating, and improving, and there's going to be a continued convergence of content and media and commerce together. They all work together, and so you really got to know both sides. Don't be the person that just the content person, don't be the person that's just the commerce person. They're going to merge together and you need to know both.

Chris Erwin:

Well put. All right, last couple. Any future startup ambitions? I know you have a lot in your plate right now.

Kevin Gould:

The key for 2021 is focus and no new brand. There's no new brands that are happening. I'm in it now with these. I love it. I think there's three really great brands and it's going to be a key to focus. Down the line, we'll see what happens, but I feel I've got the next year sort of lined up on what I'm focusing on. I'm always a startup person. I'm sure there's other things that'll pop up after that.

Chris Erwin:

Last one, it's an easy one. How can people get in contact with you?

Kevin Gould:

I try to be pretty responsive. Sometimes I can't get back to everyone, but I'm on Instagram. It's just @KevinG. LinkedIn, you can look me up. It's Kevin Gould. Those are probably the two easiest ways, Again, I try to be as responsive as I can.

Chris Erwin:

Well, Kevin, thanks for being on the podcast.

Kevin Gould:

Thanks for having me. This is a lot of fun. I think you dove into a lot of things that don't normally get talked about on podcast. I appreciate it.

Chris Erwin:

All right. One thing that really stands out to me from my interview with Kevin is that he's got really good business instincts. That being said the fact that he tripled down on his clients by taking equity through advisory, and then using a cash advance against his credit card to invest in them, and then also clearing out his Roth IRA. That's just wild to me, but massive kudos to Kevin, because that clearly worked out very well for him.

Chris Erwin:

All right. Two things to know for all you listeners. One, we just published a couple of our 2021 predictions on our blog. If you go to wearerockwater.com/blog, you can read about our predictions in the audio and podcasting space as well as in the food commerce space. Definitely worth checking out.

Chris Erwin:

Second, we're still working on our live stream media and commerce conference. That's coming up in the second quarter of this year. Again, if you want to get involved, if you want to be a speaker, if you want to be a sponsor, reach out to us. You can get in contact by emailing us at [email protected]. All right. That's it, everybody. Thanks for listening.

Chris Erwin:

The Come Up is written and hosted by me, Chris Erwin, and is a production of RockWater Industries. Please rate and review this show on Apple Podcast and remember to subscribe wherever you listen to our show. If you really dig us, feel free to forward the Come Up to a friend. 

You can sign up for our company newsletter at wearerockwater.com/newsletter. You can follow us on Twitter @tcupod. The Come Up is engineered by Daniel Tureck. Music is by Devon Bryant. Logo and branding is by Kevin Zazzali, and special thanks to Andrew Cohen and Mike Booth from the RockWater team.

Gretta Cohn is the founder and CEO of Transmitter Media. Gretta's experience runs the gamut of all things audio, from public radio and ringtones, to producing chart-topping podcasts. We discuss her time touring with the band Bright Eyes, being hired as the first production executive at Midroll Media and Earwolf, and starting her own podcast company with only $7,000 of savings. 

Subscribe to our newsletter. We explore the intersection of media, technology, and commerce: sign-up link

Learn more about our market research and executive advisory: RockWater website

Follow The Come Up on Twitter: @TCUpod

Email us: [email protected]

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EPISODE TRANSCRIPT:

Chris Erwin:

Hi, I'm Chris Erwin. Welcome to The Come Up, a podcast that interviews entrepreneurs and leaders.

Gretta Cohn:

I thought I would take the more productive path, the one where I didn't leave podcasting and I made this decision in December of 2016 to myself and then spent the next couple of months just tucking away money. And when I say I saved money before starting the business, I saved $7,000.

Chris Erwin:

This week's episode features Gretta Cohn, the founder and CEO of Transmitter Media. Now, Gretta's experience runs the gamut of all things audio. From being a touring cellist with the band, Cursive, to teaching radio workshops at NYU, to working in audiobooks, ringtones, and most recently podcasts. And Gretta's done some groundbreaking work along the way like turning Freakonomics Radio into an omni channel media brand, launching the number one podcast show, Beautiful Stories from Anonymous People and helping build Howl, which eventually became part of Stitcher. But Gretta's career transformed in 2017 when she decided to do podcasting on her own terms. So with only $7000 of savings, Gretta founded Transmitter Media and quickly began producing premium podcasts for clients like, TED, Spotify, and Walmart. Today, Gretta is focused on scaling her Brooklyn based team and creating more, as she describes, beautiful things.

Chris Erwin:

Gretta's love for her craft and team is so genuine and her story is a great example of how sheer will and passion are the ultimate enablers. All right, let's get into it.

Chris Erwin:

Tell me a little bit about where you grew up. I believe that you grew up in New York City. Is that right?

Gretta Cohn:

Well, I grew up in the suburbs, so I grew up on Long Island. My mom is from Queens and my dad is from Brooklyn and there is a sort of mythology of their meeting. My mom's dad was a butcher in Queens and my dad would always tell us that they didn't have toothpaste growing up and he'd go over to my mom's house and just eat. Yeah, they moved out to Long Island after they got married.

Chris Erwin:

Nice. And what part of Long Island?

Gretta Cohn:

Initially I grew up on the eastern end in the town called Mount Sinai and then when I was 13 in a very traumatic move at that age we moved to Huntington, which was more like smack in the middle of the island.

Chris Erwin:

My cousins are from Huntington. That's where they grew up, but then I think they moved to Lloyd's Neck shortly after. Why was that move so traumatic at 13?

Gretta Cohn:

I think it's that really formative age where you are sort of coming into yourself as a human, as a teenager and I remember writing my name on the wall in the closet because I wanted to leave my mark on that particular house that we grew up in. But then we moved and I made new friends and it was fine.

Chris Erwin:

Everything is scary at that age. It's like, "Oh, I have my friends and if I move to a new high school or middle school, I'll never have the same friends again."

Gretta Cohn:

My best friend at the time, Alessandra, never to be talked to or seen again.

Chris Erwin:

What was the household like growing up? Was there interesting audio from your parents? I mean, I think you mentioned, remind me, your father was a butcher and your mother was...

Gretta Cohn:

No, no. Those are my grandparents.

Chris Erwin:

Those are your grandparents. Got it.

Gretta Cohn:

Yeah. No. My parents were both teachers in the education system. My dad was a teacher his whole career life. He taught shop and psychology classes and computer classes. And my mom ended up being a superintendent of the school district on Long Island. She got her start as a Phys Ed teacher and then became an English teacher and worked her way up to superintendent. The sort of interest in audio they instilled in me and my two brothers extremely early. We all started learning to play string instruments at the age of three through the Suzuki method.

Chris Erwin:

The Suzuki method?

Gretta Cohn:

Yeah. Which is like an ear training style of learning music. So you essentially at three years old, you cannot possibly understand how to physically play an instrument and I remember a lot of time spent in those early group lessons just hugging the cello and singing this song, I love my cello very much, I play it every day and crawling up and down the bow with spider fingers, that's what they called it because your fingers kind of looked like spiders crawling up and down the bow and we all started playing string instruments at that age. I played cello and then the brother who came after me played violin, and the brother who came after him also played cello.

Chris Erwin:

Wow. And did you parents play instruments as well, string instruments?

Gretta Cohn:

No. My dad loves to say he can play the radio.

Chris Erwin:

I respect that.

Gretta Cohn:

I think they are educators, they are really invested in the full education of a person and so I think that they thought it was a good teaching discipline and it certainly required a kind of discipline. I can recall really fighting against practicing because I had to practice probably every day and I would rebel and not want to do it, but it was not really an option and I'm glad that ultimately I was pressed to continue to play because playing music has played such a huge part of my life.

Chris Erwin:

Clearly. It led you, which we'll get to, into founding a podcast production company and network and so much more. So very big impact. But, I get it. I began playing the alto saxophone in fourth grade and my twin brother was playing the clarinet and it was lessons with Mr. Slonum every week, an hour of practice every day and it was, when you're putting it on top of sports and homework and academics, it's a lot and it's intense and there's moments where you really don't want to do it and it's not fun and then there's moments where you're very thankful for it. And I think a lot of the more thankful moments came later in my life, but if you can get some of those early on, it's meaningful. When you first started playing, did you really enjoy it or was it just like, uh this is what I'm just supposed to do?

Gretta Cohn:

I remember enjoying it. I remember in particular being able to do little recitals every so often and I know there are photographs of myself in recital that I've seen even recently and there is such a joy in that and I think that showing off something that you've done and your family claps for you, it's a good job. Ultimately, what it feels like to play in a group, in an ensemble, it's pretty magical. I played in orchestras starting in grade school all the way up through college and there is something really amazing about the collective and your part and you can't mess up because it's glaringly obvious if you're the one out of the section of 12 cellists whose got their bow going the wrong direction or the wrong note playing. But it's also really beautiful to play in a group like that.

Chris Erwin:

Yeah. It's a special team sport, right? You rely on other people and people rely on you. When it comes together, it's an absolutely beautiful event, for you and the audience.

Gretta Cohn:

Yeah. I also played soccer growing up, speaking of team sports.

Chris Erwin:

Okay. What position?

Gretta Cohn:

I was defense. They would enlist me to run around and shadow the most powerful player on the other team. I don't know why, but I remember that.

Chris Erwin:

I was very similar. I started out as a recreation all-star like a forward and then got moved to right fullback, which is defense. That was my soccer career. All right. So interesting. So yeah, speaking of studying music, I think that when you went to university, you almost went to study music at a conservatory but you ended up going to Brown instead. What were you thinking, because were you going down a path where it's like, "I want to be in audio, I want to create music." What was your head space there as you started to go through advanced education, beginnings of your career?

Gretta Cohn:

I remember collecting fliers for conservatories. I was interested in conservatory, I think though that as I began to really think about what that would mean, I don't know that I was thinking really broadly, like oh... No one at 17 or whatever really has a full picture of what those choices ultimately mean but I'm glad that I didn't go to music school. I was always the worst player in the best section. So I remember I was in the New York Youth Symphony and I was definitely not the best player in that section, but it was really hard to get in. One summer I went and studied at the Tanglewood Institute in Boston, which is, again, extremely competitive and hard to get into but I was definitely not the best player there.

Gretta Cohn:

And I think that thinking about what it would mean to devote oneself entirely to that, I had other interests. I wasn't so completely focused on being a performer that it didn't ultimately feel like it would make a lot of sense because I wanted to study history, I wanted... And obviously, you go to conservatory, you have a well-rounded education ultimately, I would imagine, but it's not where I think I ultimately wanted to go. That was not the direction I ultimately wanted to go.

Chris Erwin:

Yeah. It's a really big commitment going from good to great, but I mean, you are great. You are getting into these elite orchestras but to be the first chair, that's a level of dedication practice that's really tough. It's funny, I actually read a David Foster Wallace article about the sport of tennis and he played and he was very good and I think he could have even gone pro, but he's like, "I'm good, I put in enough hours and I have fun with it, but for me to go to the next level..." He's like, "It's not fun to me and I don't want to do that." It's not for him. So you make a decision and you go to Brown. What's your study focus at Brown?

Gretta Cohn:

I ultimately was in the American Studies Department, but I had a special sort of crossover with the music department so I took a lot of music classes, I took a lot of American Studies classes which is basically like cultural history, social history, history through the lens of various social movements or pop culture, which I think is really fascinating and I wound everything together so that my senior thesis was about cover songs and the history of sort of copying and the idea of creating various versions of any original work and the sort of cultural history and critical theory lens of it, but also just I selected three songs and I traced their history over time from a performance perspective but also from like, how does this song fit into the narrative of music history?

Chris Erwin:

Do you remember the three songs?

Gretta Cohn:

I think I did Twist and Shout.

Chris Erwin:

Okay.

Gretta Cohn:

I Shall Be Released and I can't remember the third one. But I had a lot of fun writing it and I really liked the bridging between the music department and the American Studies department. And strangely, there are so many journalists who came up through American Studies. There are several producers on my staff who were American Studies students in college. I think it just gives you this permission to think about story telling in the world from just this very unique cultural vantage points.

Chris Erwin:

Did you have a certain expectation where you had an idea of what that story was going to be over time or were you surprised and as you saw how the narrative played out with the original song and recording and production and then the covers, anything that stands out of like, "Oh, I did not expect this, but I found this very fascinating."?

Gretta Cohn:

I don't really remember at this point.

Chris Erwin:

Sorry for putting you on the spot, it's such a long time ago.

Gretta Cohn:

The thing was like more than 100 pages and it's probably a door stopper now at my parents house. I remember that I put a big picture of a mushroom on the last page. John Cage wrote a lot about mushrooms and so I wove some of his work into the thesis but this idea that the mushroom takes the dirt and crap and stuff that's on the forest floor and turns it into this organic material, the mushroom. So yeah, I don't remember the specifics.

Chris Erwin:

Yeah, no. All good. My thesis was on the Banana Wars and that is... It's not even worthy of being a door stopper. That's just straight to the trash. But I did, for a music class, I think I did break down a song by the Sex Pistols.

Gretta Cohn:

Cool.

Chris Erwin:

I can't remember specifically which one, but I think I dove deep into the lyrics and I think I was pretty disappointed. I expected to find more meaning and have more fun with it, and I think it was maybe my young mind, I couldn't go deeper than I thought I could. Anyway... So fast forward to 2001 and as I was going through your bio, this really stood out and it hits close to home. You become a cellist for some alternative rock bands including Cursive, The Faint, and Bright Eyes. And I just remember The Faint, I think a song from 2008, The Geeks Were Right. I remember listening to that shortly after college. So tell me, what was that transition going from university to then moving, I think you moved to Omaha out of New York to play in these rock bands?

Gretta Cohn:

So when I was in college, I continued to play in the school orchestra, but I also met some friends who became collaborators and we would just improvise in the lounge like, bass drums, guitar and cello. And that was really freeing for me. Growing up on Long Island, I had such easy access to New York City and for whatever reason, I was really given a lot of freedom to... I would take the Long Island Railroad into Manhattan and go to concerts all through high school, like rock concerts.

Chris Erwin:

What was some of your earliest concert memories?

Gretta Cohn:

Purposely getting to an Afghan Whigs show and planting myself in the front row because I wanted to be as close as possible to the stage. So I used to go to concerts all the time and I was really, really interested in... I wasn't only a person who thought about classical music at all and so I met this group of people and formed this little group together and so I was playing music in college, eventually joining a band mostly with locals in Providence and we became the opening act for a lot of bands that were coming through.

Chris Erwin:

And what type of music were you playing, Gretta?

Gretta Cohn:

It was arty rock.

Chris Erwin:

Arty rock. Okay.

Gretta Cohn:

Yeah. Some of it was instrumental, but then some of it was like pop. I think one of the bands that I was in was called The Beauty Industry and it was probably a little bit reminiscent of Built to Spill and The Magnetic Fields and a little bit like Poppy. So in that band we would serve as the opening act for a lot of artists that were coming through and through that I was able to meet the folks from Saddle Creek from Omaha, Nebraska. And I didn't know that I made an impression on them, but I did and after I graduated I moved to New York. I didn't really know exactly where I was headed. I got a job working in the development office at Carnegie Hall and I didn't love it. We had to wear suits. And one day the folks from Omaha called my parents home phone and left a message and asked if I would come out and play on a record with them and I did.

Chris Erwin:

When you got that message, were you ecstatic, were you super excited or were you just confused, like, "Hey, is this real? What's going on here?"

Gretta Cohn:

Yeah. I think I was like, "Huh, well, that's interesting." Like, "I didn't expect this." So Cursive is the group that invited me out to record. Just sort of like come out and record on our album. And I didn't actually know Cursive. I had met Bright Eyes and Lullaby for the Working Class when I was at Brown, but I hadn't met Cursive and my best friend, who is still one of my best friends was a Cursive fan and dumped all of their CDs and seven inches in my lap and was like, "You need to listen to them, they are so good." So I did and I sort of gave myself a little Cursive education and then I started to get really excited because I felt like there was a lot of interesting potential. Yeah.

Gretta Cohn:

Moving out there was not an easy decision. It was very unknown for me. I love New York City and I always imagined myself here and I had never been to the Midwest so I didn't know what my expectations were and I didn't... Also at that time Cursive was a fairly well-known band but it wasn't understood that I would move out there and that would be my job, right? I was moving out there to join this community and play in Cursive and do Cursive stuff, go on tour, record records, but at that point there was no promise like, "Oh, I'm going to live off of this." And so I went to a temp agency and I did paperwork in an accountant's office and-

Chris Erwin:

While also performing with Cursive?

Gretta Cohn:

Yeah. Yeah. I will also say though, after the first year, things really took off after The Ugly Organ and I would say at that point I was no longer working in the temp office and we were going on long tours and when I came home in between stretches on tour, I was recovering from tour because it's quite exhausting and working on the next thing with the bands.

Chris Erwin:

Were you touring around nationally? Any international touring?

Gretta Cohn:

Yeah. National and international. We went all over the States, Canada and then European tour is like often... Cursive was very big in Germany so we would spend a lot of time in Germany, Scandinavia. We went to Japan once.

Chris Erwin:

What an incredible post university experience!

Gretta Cohn:

It really, really was incredible.

Chris Erwin:

Playing music because of a skill that you formed very early on and then working in New York at Carnegie Hall and a job that you weren't too excited about and then you just get this serendipitous phone call. And you started listening to Cursive records in seven inches and you're getting more and more excited and all of a sudden you're traveling the world. That's like a dream scenario.

Gretta Cohn:

Yeah. It was pretty dreamy. And I think I recognized at the time. I mean, those first tours, we were sleeping on... I had my sleeping bag and we would be sleeping on hardwood floors, end up in like a row and someone's apartment in like Arlington. And I remember some of those first tours internationally, like in Germany, you would play the show and then everyone would leave and they would shut the lights off and we would just sleep on the stage. And in the morning the promoter, like the booker would come back and they would have bread and cheese and fruit and coffee. And it was just this beautiful... But we were sleeping on the stage.

Chris Erwin:

I mean, you're all doing it together. So it was cool. Right. You just were a crew.

Gretta Cohn:

Yeah, yeah. It was great. I loved it. I really, really loved it.

Chris Erwin:

I look at your work timeline between 2001 to 2010, which includes, you're a touring international artist, but then you do a lot of other things in audio. Like you study with Rob Rosenthal at the Salt Institute, do some time in Studio 360, and then you go to radio and then audio books. So what are the next few years? How does this audio adventure start to transform for you?

Gretta Cohn:

While I was in Cursive, there were other parts of me that I felt needed feeding and so I started writing for the local alternative weekly in Omaha. And I was doing like book reviews and reviewing art shows and doing little pieces, which sort of opened up to me, this understanding that journalism was something that I was really interested in. And while I was still essentially based in Omaha and still, essentially based out of Saddle Creek, I came back to New York for a few months and did an internship at The Village Voice because I just really wanted to sort of start exploring these paths of what would potentially come next. I didn't necessarily think that I was meant to stay in Omaha like for the rest of my life. When I first moved out there, I thought, "Oh, I'll give it a few years. See how it goes and then probably come back home to New York."

Gretta Cohn:

And then things really took off and so I didn't want to leave. And I was really having a great time and loved it and loved everything that I was doing. And I think that at the time that chapter was coming to a close, it was sort of like naturally coming to a close and I wasn't entirely sure what I wanted to do next. I was interested in journalism, I was interested obviously in... still thinking about music and audio although I think I needed a break from music after that time. Like when you're so intensively working on something like that, you just need a minute to let everything kind of settle.

Chris Erwin:

Yeah. It's all encompassing. Right. You're just living, breathing, eating music and the band. It's a lot.

Gretta Cohn:

Yeah. So I took a couple of years and started to figure it out. Actually, something that's not on your list is I worked at a ringtone company for a bit.

Chris Erwin:

It is audio based. So I'm not surprised. So yeah, tell me about that.

Gretta Cohn:

It was just a job that I got. Actually, looking back now, I think that it was a company that was founded by two classical musicians. They mostly had contracts with major record labels and I remember turning Sean Paul's Temperature into a ringtone in particular. It was just like chopping things into little eight seconds and looping them and mastering them and-

Chris Erwin:

Were you doing the technical work as well?

Gretta Cohn:

Not really, you spend time in the studio and so you learn and you pick up things. I wasn't recording the band, but that was the first time that I got my own pro tools set up and so I had my own pro tool setup, like was using it for my own little projects at home, but I was not technically involved with the making of any of the records that was on now, except for playing on them.

Chris Erwin:

Yeah, you were dabbling in pro tools then pretty early on.

Gretta Cohn:

Yeah, yeah. I had the original Mbox, which is like this big plastic, weird alien looking object with just like a couple of little knobs on it. I finally got rid of it a couple of years ago. I held onto it for a long time and now you don't even need it.

Chris Erwin:

So you're dabbling and then I know that you spend time as a producer at The Story with Dick Gordon, North Carolina, and then you went to audio books. Is that when things started to take shape for you of knowing kind of what you wanted to do?

Gretta Cohn:

I think as soon as I went to Salt to study with Rob Rosenthal is when I knew that that's what I wanted to do. I took a few years after Cursive to kind of reset a little bit and then I started working at the ringtone company and began to have conversations with people about where all my interests collided. Like I loved working in sound, storytelling and journalism were really important to me. I don't think at that point that... There was a whole lot that I was exposed to apart from NPR, This American Life and Studio 360 were sort of the major outlets for audio storytelling that I understood and spent time with. And I just remember having a meal with someone who I don't recall his name, but he's done a lot of illustrations for This American Life and public radio outlets and he was like, "There's this place, it's called salt. You can learn how to do this there." And so I just decided that I was going to step down this path. Right.

Chris Erwin:

Yeah. And Salt is based in Maine, is that right?

Gretta Cohn:

Yeah. So I moved to Maine for six months. I was very excited. I got a merit scholarship to go there.

Chris Erwin:

Oh wow.

Gretta Cohn:

Yeah, and I basically... There's so many fundamentals that I learned there that I use every single day now still. I think Rob Rosenthal is absolutely brilliant and he has trained so many radio producers. It's insane.

Chris Erwin:

Of all the learnings from Rob, just like what's one that comes to mind quickly that you use everyday?

Gretta Cohn:

I don't know that this is one I use every day, but it's one that's really stuck with me, is he really counseled to be really mindful when thinking about adding music to a story. He used the phrase, emotional fascism. Essentially, if you need to rely on the music to tell the listener how to feel, then you haven't done your job in sort of crafting a good story. So like the bones of the story, like the structure, the content, the sort of stakes intention and the character you've chosen, like all of that have to clear a certain hurdle and then you can start thinking about adding music, but if you're relying on the music to sort of create tension or drama or emotion, then you've kind of missed something.

Chris Erwin:

Yeah. That's very interesting. What a great insight! I like that. Emotional fascism.

Gretta Cohn:

I'll never forget.

Chris Erwin:

So after the Salt Institute, what's next?

Gretta Cohn:

I got an internship at WNYC at Studio 360. At that time the internship system at New York Public Radio was like largely unpaid. I think I got $12 a day. So I interned I think three or four days a week and then I had like two other jobs.

Chris Erwin:

Just to make ends meet, to make it work.

Gretta Cohn:

Yeah. I worked at a coffee shop, like most mornings. And then I worked at a Pilates studio many afternoons and on the weekends. So it was like a lot, I was really running at full steam, but I really enjoyed the internship there. And then that was my first real glimpse into what it was like to work in a team to make impactful audio storytelling and I learned a lot there too. The team there was really amazing. Yeah. So Studio 360 was fantastic. And then a friend of mine had found out about this gig at The Story with Dick Gordon. It was a short term contract producer role, like filling in for someone who was out on leave. And I got the job and I moved down to Durham, North Carolina, and found an apartment, brought my cat and worked on that show for a few months, which I think was a pretty crucial experience to have had, which helped open the door into WNYC.

Chris Erwin:

Why's that?

Gretta Cohn:

So this was in like 2008, 9 and there weren't like a whole lot of opportunities in the audio storytelling space. Like your major opportunities were at public radio stations and public radio stations were highly competitive. It didn't have a lot of turnover. They understood that they were the only game in town if this was the career path that you were interested in going down. So having had a job at a radio station on staff on a show was such a huge opportunity. I don't know that I was like chomping at the bit to leave New York or move to Carolina, although I loved it there. And I had friends who lived there that I knew from the Saddle Creek community. So it was really great. I moved down there and I didn't have to... I can't recall ever feeling lonely. Right. Like I immediately had this community of people, which was amazing, but that gig was only three months.

Gretta Cohn:

And so I came back to New York and basically spent the next couple of years banging on the door to get back into WNYC, which is when I went to the audio books company where quite a few radio producers worked. Like that's how I found out about it. There were folks who had passed through Studio 360 or elsewhere. And my boss at the audio books company is David Markowitz, who is now currently working in the podcasting department at Netflix. And he previously was at Pushkin and at Headspace and he... So he and I, although our paths crossed at that moment, because our paths have continued to cross over and over again since that time working together with the audio books company. Audio books wasn't my passion, but while I was there I got the idea to pitch the podcast to the audio books company, which they agreed to let me do. And so I had this outlet to just do a little bit of experimenting and to grow some skills and also have just like an outlet to doing this kind of work that I wanted to be doing.

Chris Erwin:

Had you ever pitched a project or an idea before to any place that you worked at?

Gretta Cohn:

I pitched stories to Studio 360, but to pitch an idea for something that had not existed before, no.

Chris Erwin:

It becomes, I believe, The Modern Scholar podcast, is that right?

Gretta Cohn:

Yeah. You've done like a really deep research.

Chris Erwin:

Look, it helps to tell your story. Right. So you pitch, and then you get the green light, which must feel validating. It's like, okay, this is a good idea, but now it's got to be more than a pitch, you had to execute. Was that intimidating or were you like, "No, I'm ready to go I got it."

Gretta Cohn:

I was ready to go. They had an audio book series called The Modern Scholar. Professors would come in and record like 10 hours worth of like Italian history. And so what I did was just have a one hour interview with the professor who was the author of this series and talk about their work, go into detail on something really specific. I will say at that time that like I applied for a mentorship with AIR, the Association of Independence Radio, they gave me a mentor and I had like a few sessions with him and it was great. Like I had someone... I had an editor, right. I wasn't totally on my own kind of like muscling through. And so he really sort of helped refine the ideas for that show and that was a great help. So I'm lucky that I was able to get that.

Chris Erwin:

What I'm really hearing Gretta is that you moved around a lot and participated in and developed all these different music and audio communities around the US and even the world from like Omaha and international touring and Scandinavia and Europe, and then the Salt and Maine and North Carolina and New York and more, and I'm sure, as you said, with David Markowitz, that these relationships are now serving you in your current business. So it feels like that was like a really good investment of your time where the networking was great, but you also learned a lot and were exposed to a lot of different thinking and ideas. Is that right?

Gretta Cohn:

Absolutely. Definitely. Yeah.

Chris Erwin:

After dabbling around a bit for the first decade of the 2000s, you then go to WNYC and you're there for around six years, I think 2008 to 2014. And you work on some cool projects. You're the associate producer at Freakonomics and you also work on Soundcheck. So tell me about what made you commit to WNYC and what were you working on when you first got there?

Gretta Cohn:

At the time there weren't a lot of options for people doing this work. And WNYC obviously is an incredible place where really amazing work is done, really talented people. It basically was like the game in town, right? Like there weren't a lot of other places where you could do audio storytelling work in this way. There was a pivotal moment that I think could have gone in a different direction, but I had applied for a job at StoryCorps and I applied for the job at Soundcheck.

Chris Erwin:

What is StoryCorps?

Gretta Cohn:

They have a story every Friday on NPR that's like a little three minute edited story and it's usually like two people in conversation with each other. It's highly personal. And they're very well known for these human connection stories. It's I think influenced in part by oral history and anthropology, but it's basically this intimate storytelling. And I did not get that job, although I was a runner up and the person who did get the job is now one of my closest friends. But at the same time was an applicant for Soundcheck and I did get that job. And I think it was... That was the right path for me because I have such a passion for music. Right. My background kind of really led me to have an understanding of how to tell those stories.

Chris Erwin:

What is the Soundcheck format?

Gretta Cohn:

It changed over time. But when I joined Soundcheck, it was a live daily show about music and really open, like wide open as far as what it covered. So in any given episode, you could have like Yoko Ono there for an interview, you could have the author of a book about musicals from the 1920s, and then you could have like a live performance from Parquet Courts. So it was really wide ranging and varied and super interesting. And there's so much about working on a daily show that's I think extremely crucial to building up chops as a producer because every single day you have a brand new blank slate, you have to work extremely quickly and efficiently. Working in the live setting can create so much pressure because not only are you keeping to a clock, like the show went from like 2:01 to like 2:50 every day, and there had to be certain breaks and you have an engineer and you need the music to cue in a certain place.

Gretta Cohn:

And so you're like, "Cue the music." And you're whispering to the host like, "Move on to the next question." You're like this master puppeteer with all these marionettes and it's pretty wild. It's really fun, super stressful. You go off stage and it's like-

Chris Erwin:

It sounds stressful.

Gretta Cohn:

You can't fix it. You just have to move on and you learn a lot.

Chris Erwin:

It feels like something, you do that for maybe a couple of years or a few years and then it's like, ah you need a break from that. It's amazing that people who work in like live video or live radio for decades, like kudos to the stamina that they build up.

Gretta Cohn:

And that's exactly what happened is I needed a break from it. And that's when I went to Freakonomics.

Chris Erwin:

Got it. Before we go into Freakonomics, you also helped create Soundcheck into an omni-channel media brand where you were launching video and live events and interactive series. Was that something that had been happening in the audio industry or were you kind of setting a new precedent?

Gretta Cohn:

Our team was tapped to reinvent Soundcheck. So it had been this live daily show for quite some time and I think that WNYC wanted to reshape it for a variety of reasons. So we were sort of tasked, like we pulled the show off the air and kind of went through this like sprint of re-imagining, what the show could be, how it would sound, what it would do. And actually, I remember that I pitched this video series that was a lot of fun. I can't remember the name of it now, but we worked with a local elementary school and we would have three kids sitting behind desks and we would play them clips from pop songs-

Chris Erwin:

Whoa.

Gretta Cohn:

... and they would review them and-

Chris Erwin:

That's a really cool idea.

Gretta Cohn:

... it was awesome. It was so much fun. We did a lot of live performances and I started producing sort of like more highly produced segments and storytelling for Soundcheck at that time, because there was more space to try and figure that out. Ultimately, what it turned into was like a daily delivery of a show that I think ultimately resembled the old show in many ways, but it was not live anymore. And there were all these other tasks. I also created a first lesson type series for Soundcheck at that time where we would like stream a new album before it came out and I would write a little review. It was really fun. When we pulled the show off the air and we were tasked with re-imagining it was like a sandbox that you just kind of could plan, which was great.

Chris Erwin:

It's a wide open canvas that you can paint to how you desire. I get that why you were burnt out after that. So then you change it up and you become an associate producer at Freakonomics and you work with the fame, Stephen Dubner and Steven Levitt. How has that experience?

Gretta Cohn:

It was great. It was challenging. I think that show has incredibly high standards and there's a particular kind of brain that I think works extremely well at that show. At the time, there were two of us who were the producers of the show, myself, who has this background in music and in production. And then the other producer was an economist who had been freshly graduated from economics school. And so we were this pair and I think what ultimately happened was that where I shown where these like human stories and where he shown was like distilling econ papers into sort of understandable stories. And so I think the two of us together really complimented each other. One of my favorite episodes that I worked on was about the Nathan's hotdog contest and one of the sort of like champs who had come up with a particular system for how to win-

Chris Erwin:

Dunking them in water and all that stuff. Yeah. I remember watching some of those segments online. In a minute they put back like 47 hotdogs. It was something crazy.

Gretta Cohn:

Yeah, it's wild.

Chris Erwin:

After Freakonomics, you decided to depart for Midroll and Earwolf. What was the impetus for that?

Gretta Cohn:

My time at Freakonomics was sort of like naturally coming to a close. I think that while my strength was in this sort of human sort of storytelling, I think the show needed someone who had a little bit more of that like econ background. And so I started to look around the station at WNYC, of other places where I could land, right? Like I'd moved from Soundcheck to Freakonomics, like what would be the next place for me to go? And I couldn't find it. I spent a little bit of time in the newsroom helping to look for a host for a new health podcast and I had conversations with people around the station about various other shows. I think I talked to the folks on the media and this producer, Emily Botein, who ultimately founded the Alec Baldwin podcast and a host of other really great shows there, but it didn't seem like there was space or a role that really made sense for me as far as like the next step is concerned.

Gretta Cohn:

At that time, Erik Diehn who's now the CEO of the Stitcher empire was in the finance office, I think at WNYC and he left to go to Midroll/Earwolf.

Chris Erwin:

I didn't realize he was also WNYC. Bannon was also WNYC who's now the chief content officer over there?

Gretta Cohn:

Mm-hmm (affirmative).

Chris Erwin:

Wow. It was a feeder to that company.

Gretta Cohn:

Yeah. So Erik Diehn left WNYC and I remember the note that went around, he's going to this company, Earwolf/Midroll. And I was like, kind of filed that away. And then it was probably a few months later that they put a position, they were hiring for a producer. And I sort of leapt at the opportunity. I thought that the shows on Earwolf were awesome. I had not worked really in comedy. Although I think that there's so much crossover in Soundcheck. We really had a lot of license to have basically like whoever on the show, like I booked comedians, I booked authors. Like I booked anyone who had a passion to talk about music, which is like 90% of the world. And so I think that that was really of interest to them. And I had a couple of conversations with Erik and the job was mine. I mean, I went through-

Chris Erwin:

You make it sound very easy.

Gretta Cohn:

... a proper vetting and interview process. And there were other candidates, but they gave it to me. And I was really, really excited because I think I was ready for a fresh start and I was ready for something new, something a little bit unknown. I think that I tend to find... Typically, I think if you look over the course of my life, like every few years, I'm like, "Okay, what's the next thing?" And I think that I still feel that way except now I have this entity of Transmitter in which to keep iterating and playing, but I was just ready for the next thing. And it was at that time, a really small company, I was the first New York based employee, like Eric was living in New Jersey. So it doesn't count as a New York employee. There was no office.

Chris Erwin:

I remember that Jeff Ullrich was the founder and it was bootstrap, didn't raise any venture capital and started I think in the early 2000s, if I remember correctly. Is that right?

Gretta Cohn:

I don't know the dates, but that sounds right.

Chris Erwin:

Okay. A little context for the listeners. And Earwolf is a comedy podcast network. So there's a slate of comedy shows and Midroll was the advertising arm of the business that would connect advertisers with the podcasters. But no, please continue. So you're the first New York hire.

Gretta Cohn:

Yeah. Which was really exciting to me. I was the first producer hired by the company. They had a few really amazing audio engineers out in LA who ran the recordings and they did editing, but there had never been a producer on staff. So it was really this like wide open field. And Jeff at that time, I think had taken a step back from the company, but the moment that I was brought in is when the idea for Howl came into the picture and Howl was a membership subscription-based app that has now turned into Stitcher and Stitcher Premium, it was folded in, into Stitcher and Stitcher Premium. But at the time there was like this real push to create a subscription-based app with like a ton of new material. And one of my first jobs was to work extremely closely with Jeff to figure out what was going to be on this app, who were we going to hire to make material? What producers, what comedians, what actors? There was an enormous spreadsheet, like one of the most enormous spreadsheets that I've ever spent time with.

Gretta Cohn:

So that was my first task and alongside, which was to sort of from a producer's perspective look at this later shows on Earwolf and start to think about what would a producer bring to the network? What would a producer bring to the hosts, to the way that things were made, to new ideas to bring to the network? And so those two things were sort of happening concurrently.

Chris Erwin:

The producer role was not defined. You're the first producer there. So it's you coming in saying, "Here's how I can enhance the slate. Here's how I can enhance the content strategy of where we're headed concurrently with we're launching Howl, which needs a lot of content, both from partner podcasters and probably owned and operated and then filling..." So creating a new slate, that's going to fill that. That's going to make people want to buy the membership product or subscription product, which are big questions that Spotify and Netflix and the biggest subscription platforms in the world have huge teams to figure out. And it's like you and Jeff, and maybe a couple more people?

Gretta Cohn:

There was one developer.

Chris Erwin:

Wow.

Gretta Cohn:

It was intense. It was a lot of work. I remember because at that time too, I was the only New York based person. Eric was in New Jersey. I think Lex Friedman came along. He was either already there or came along shortly thereafter, also based in New Jersey.

Chris Erwin:

And Lex was running sales?

Gretta Cohn:

Yes. And he's now with ART19, but there was no office. I was working from my kitchen table, much like I do now. It was great. I think what really excited me was like the open field of really sort of figuring out what everything was going to be and it was like off to the races.

Chris Erwin:

So I actually reached out to a few people that we mutually know to just get like, oh, what are some stories I can have Gretta talk about from the early Midroll/Earwolf days. So I reached out to Adam Sachs who was also on this podcast earlier. He's a childhood friend of mine that was also the CEO of the company when it sold the scripts, as well as Chris Bannon, who I consider one of the most like delightful humans on the planet. I think he was the chief content officer while you were there and he still is now under Eric as part of this new Stitcher Midroll combined empire. And what Chris said is that, like you mentioned Gretta, no office for the first six months and that you were taking meetings, I think in sound booths as well. And that when you finally did get an office, it was so small that you were taking turns sitting down.

Gretta Cohn:

Yeah. Well, we put our own furniture together. I learned so much from my years at Earwolf that have completely guided and shaped a lot of how Transmitter kind of came into being. Yeah, we put all of our furniture together ourselves in this first office.

Chris Erwin:

That's good training for you launching Transmitter where it's lean budgets, you're funding from your savings. You probably had to set up your own furniture yourself too. So that DIY attitude persists.

Gretta Cohn:

Yeah, yeah. And it was exciting. Whereas a place like WNYC is this like well oiled machine, it's also like a big ship that in order to turn 30 people have to be sort of moving things around and like, is the sky clear? There are just like so many little tiny steps that have to be taken to make a decision. Whereas what working at that early stage at Earwolf meant was like you can just make decisions, you just do it. Eric and I went around to see like five different offices. We decided together, "Oh, let's take this one on Eighth Avenue." This is the furniture. All right, let's put it together. I remember walking into the office when the furniture was first delivered and it was extremely dusty and we were wearing dust masks and trying to figure out where's the studio going to go? And it was just really exciting. It's really exciting to sort of pave your way and build something from the ground up.

Chris Erwin:

I like what you're saying too, is that you can just get things done very quickly. And that's actually one of the things that Bannon brought up about working with you is you guys launched good shows I think in just a matter of a few months or less, like Bitch, Sash and Beautiful Stories from Anonymous People, which was a number one hit on iTunes. And that now making shows like that, if you're at a bigger company with all the bureaucracy and the approvals can take over a year, but you guys were getting stuff done fast, there was no alternative choice.

Gretta Cohn:

Yeah, we were working very quickly.

Chris Erwin:

So I'm curious to hear like Beautiful Stories from Anonymous People. That's like an iTunes topper. Was that the first big podcast hit that you had in your career?

Gretta Cohn:

I would say so. Yeah. I'm trying to remember what if anything came ahead of it, but I'm fairly certain that some of my first meetings after joining the team at Earwolf were with Chris Gethard and working with him on sort of early prototypes of Beautiful Stories from Anonymous People. And he's a remarkable person. He's a brilliant comedian. He's such a good human being. He's an amazing collaborator. And yeah, it was the two of us for a while just, I think the first call that we took, which was sort of just the prototype, the pilot for the show. We're like, "We don't know what's going to happen. Is anyone going to call?" And yeah, I mean, it was really awesome working on that show. And also it was such a departure from the kinds of projects that I had worked on previously, which were extremely buttoned up like very highly produced in the sense that every single step that you took in the process was regimented, right? Like making a Freakonomics episode, making an hour of Soundcheck, thinking about that live daily experience.

Gretta Cohn:

Like you can't have a minute on the clock that's not accounted for in making those things. And here's a show where we just open a phone line and see what happens for an hour. And it's so freeing to be sort of separated from that regimentation and working with Chris Gethard, I think taught me that you can make something that's really compelling and that's really good. And it was highly produced. Like a lot of thought went into it. There's a lot of post-production, but it didn't need to be the kind of thing where like every single minute of that hour was a line on a spreadsheet. And I love that show. I think that we're all like voyeurs of other people's experiences. Right. And I think it's super interesting the way that people are willing to call and sort of like bare their souls to Chris and working on that show was fantastic.

Gretta Cohn:

And it was really gratifying and really rewarding when we realized that people were paying attention and they were going to listen. And for that to be one of the first projects of my tenure at Earwolf was great. It was great.

Chris Erwin:

That's awesome. What a cool story! Bannon even mentioned you work on, I think Casey Holford's Heaven's Gate, which is now an HBO Max series. I think that just came out this week or something, some big projects. All right. So look, in 2015, Midroll/Earwolf sells to Scripps, EW Scripps. Then I think in 2017 is when you start Transmitter Media. I'm curious to hear that after this fun sprint at Midroll and the sale and launching the shows and launching Howl and Wolfpop and all the things, what got you thinking about becoming a founder, which is a very different experience than what you had done for the first 10, 15 years of your career?

Gretta Cohn:

So after the sale, I think that Adam Sachs kind of offered me the opportunity to reshape my role a little bit. So I had been overseeing the Earwolf shows, developing and producing brand new shows and Howl was in the rear view at that point for me, I believe. I think this is like a classic situation. They're like, "We're going to split your job into two, which half do you want?" And I was like, "This is great." Because it had been a lot to be developing new shows, to have this sort of slate of shows at Earwolf requiring my attention. And I picked the path of new development and that's when they went out and found someone to executive produce the Earwolf network. And in my new role, I needed to build a team and a division.

Gretta Cohn:

So I had to hire really quickly about six producers to form a team. And there wasn't really a human resources and so it really fell on me to read every application that came in and kind of vet all of the candidates and begin that process of selecting who to talk to. And I probably spent about six months just interviewing. I think that I learned a lot from that process and I think it developed in me like a little bit of an eye for how to spot talent and people that I want to work with, but it also was like supremely exhausting. And at the same time, I think that the company was in a real state of renewal and flux and change following the sale to Scripps, which I think is probably common in any situation where a company is acquired by a company that has a different POV, like maybe doesn't understand podcasting, has its own goals that are separate from what the goals had been at Earwolf.

Gretta Cohn:

So there were just a lot of strategy shifts that I did my best to kind of keep up with, but ultimately found myself thinking like, "Well, if I were setting the strategy, what would I do? If I were re-imagining sort of the direction that this company was going in, what would I do?" And I looked around and Pineapple Street had been around for a few months, maybe six months. And I went and had some chats with them about sort of like what they were doing and what they wanted to do. And I went over and had a chat with the folks at Gimlet thinking like maybe there would be a place for me there, but ultimately out of my conversations with all of those people, was this kind of clarifying feeling that there was something that I wanted to do and that I wanted to do it differently. I would say it was definitely like burnout that kind of led me to thinking about what I wanted to do next, because it felt like where I was at was like a little bit unsustainable. It was scary.

Gretta Cohn:

I definitely spent a month sort of quaking with fear on the couch. Like, is this something that I'm going to do? What does it take and what do I need and are there like, long-term consequences that I can't really think of yet? Because I'd always had a job, right? Like I always worked for someone else and enjoyed the freedom, frankly, that that gives you, right? Like you show up, you do the work and then you leave and you can go and take care of whatever. So I just spent a lot of time thinking about it and talking to friends, my close friend who gave me the Cursive records back in the day has run a press, a small press for nearly as long as I've known him. And it's a small non-profit, but it requires the same levels of sort of like entrepreneurship and sort of like-

Chris Erwin:

Discipline in a way.

Gretta Cohn:

Yeah. Discipline. That's exactly the word. And so I talked to him a lot about he figured out what he was doing. My brother has had his own post-production business for film for more than five years, so I went for dinner with him and talked about... His business relies on film clients who come to him with a movie that needs mixing and sound effects and sound design. So we talked about that and my husband was acquiring a business. He purchased a retail shop in our neighborhood around the same time too. So there was like a lot of this around me where I had just a lot of conversations about this and I decided to do it. I decided that like the fear was not a good enough reason to not do it. And my alternate path to be quite frank was to leave podcasting because I just couldn't see where my next step was going to be.

Gretta Cohn:

And so I thought I would take the more productive path, the one where I didn't leave podcasting and I made this decision in December of 2016 to myself and then spent the next couple of months just tucking away money. When I say that I saved money before starting the business, I saved $7,000. Like this is not an enormous coffer of like startup money, but it was enough to pay for an office space and to pay for myself for a couple of months to just see what would happen. And I gave extremely early notice at Midroll and I started to look for clients before I left. So I set it up so that by the time I finally left Midroll in the end of March of 2017 and walked into my office, my new office for Transmitter Media, on the 3rd of April of 2017, I already had clients. So this also gave me that added security of like, "I'm not just walking into this empty pit of like who knows what? Like I have work to do."

Chris Erwin:

Look, that's just like an amazing transition story, but a couple of things stand out. One it's like double entrepreneur household. A lot of couples that I talk to will say, one will start a new venture business that's risky while other has like W2 salaried income. But your husband had just bought a local retail shop in the neighborhood. You were launching Transmitter Media. So you were smart about mitigating risk of landing of clients in advance. Yeah, it's a lot to take on. And the second thing I heard that I think is really interesting is you felt that there was no path for you to stay in podcasting unless you started your own business. So it's either get out and do-

Gretta Cohn:

It felt that way.

Chris Erwin:

Yeah. Get out and do something totally different or commit and go deeper with this incredible network and skillset that you've built up for a decade and a half and start your own thing. You committed to it. And yeah, whether it was meager savings of $7,000, it was enough. And you had the confidence. And I think in the early days, confidence is everything that you need. Tell us about what is Transmitter Media or what was it at that point?

Gretta Cohn:

Transmitter Media was born as a full service creative podcast company, meaning primarily working for clients who needed podcasts production. And it's really 360 ideation. There's like a paragraph that explains what they want the podcast to be and then we figure it out from there. Like it's quite rare that someone comes in the door and they have like a fully fleshed out idea for a show that has all the episodes outlined and the guests and then this and then that. So it's really starting with a kernel of an idea, figuring out how to make it, what it needs, what's the format and executing it all the way up to launch and continued production. And I think that I saw what Pineapple Street was doing. I respect Jenna and Max from Pineapple Street so much.

Gretta Cohn:

And it felt like the right model, essentially doing what film production companies do or in a way kind of like what advertising agencies do. You have clients, your clients have a story that they want to tell and as a production company, you figure out how to tell it and how to tell it really well. And I think that for me, having a focus on craft was really important quality over quantity and taking the time to really figure out creatively, what does something need was how I stepped into it.

Chris Erwin:

Clearly as the industry is growing, in terms of more audio listenership, more brands wanting to figure out the space and still early, I think in 2019, the ad market for audio was like 750 million. So you started the company is like two to three years before that, when you look at the total advertising landscape, which is like over, I think, 600 billion globally. But brands are leaning in, they want to figure it out and you have a knack for audio storytelling, and then you commit. And so who are some of the early clients you work with? I think they were Walmart and Spotify. And what did those first early projects look like and had you had experience working with brands before? Or was it like, "All right, I have a skillset, but I kind of got to figure this out on the fly too."?

Gretta Cohn:

So it was Walmart, Spotify and TED I think were the three sort of major clients at the very beginning. I hadn't worked directly with brands. I understood working with other media institutions. I understood working with hosts. I also understood developing new shows because that's what my team did at Midroll, Stitcher, Earwolf. Before I left, an entire year of just coming up with ideas and piloting them and throwing them at the wall and kind of running them through PNLs and doing all of that. And so I understood all of that. So we have worked directly with brands, but with Walmart, it was running through an advertising agency full of really great creative people and so we were interfacing more with them. And I think that I learned through them a little bit more about how to work with a client like Walmart.

Gretta Cohn:

But I think also that everyone we were working with at that time was also trying to figure it out for themselves in a brand new way. So we've now been working with TED for over three and a half years, but at the time the show that we developed with them, WorkLife with Adam Grant, I think was their first sort of step into the sort of slate of podcasts that they have now. They had TED talks daily. It was sort of concurrently like I know what the steps to take and the people that I am making these podcasts for don't, they've never done it. And so I think I learned a lot in those first few projects about how to deliver, how to communicate what we're doing clearly. But it's not like I hadn't already done that before. Like I had the skills, it's just was like refining them and putting them into this really particular box.

Chris Erwin:

Yeah, just a little bit of a different application. Makes sense.

Gretta Cohn:

Yeah, exactly.

Chris Erwin:

When we were talking about having to build a development team at Midroll and Earwolf that you said that you had like a unique sense of how to identify good people. So then you start building your own team at Transmitter and it seems that you've built a pretty special team there. So what was your, like when you think about, if I need great people to make Transmitter a success, what type of people were you looking for and what has like your culture become at your company?

Gretta Cohn:

I love my team so much. I agree. I agree I think they're really special. I think independent thinkers, people who have a really unique creative spark, people who surprise me. Right. I think that what I learned in doing all this interviews at Midroll was like, I prepare a lot for interviews, kind of much like you prepared for this. I would do deep dives. I would listen to a lot of work from the people who were coming into... had applied for the roles. I also like over the years, there are certain producers who I'll just kind of keep in touch with, or follow their work and be excited by their work and hope that one day they might like to come work at Transmitter. And so I also am really keen on people who have a collaborative spirit. So an independent thinker who's down to collaborate, who doesn't necessarily need to put their fingerprints all over everything and it's like cool if their fingerprints kind of merge with other people's fingerprints and we've got this really sort of group dynamic where we're really, everyone is contributing towards something.

Gretta Cohn:

And people own projects, people own stories, people own episodes, but ultimately, I think that we have a very collaborative team environment. And we're also a group of people who like to celebrate our successes, even like the teeniest tiniest ones. And so we spend a lot of time like talking about the things that go well and I think that creates a lot of pride in work. And I'm interested in working with people who have that same sense of craft as I do. It's not necessarily about perfection, but it's about doing really good work, making something sound as good as it can possibly be. We have an episode that on Monday I got an email about, saying, "This is in its final edit. I'm not looking for any big edit changes. I'm only looking for a notes on music." And I listened to it and I was like, "Ah."

Chris Erwin:

Is this from a client?

Gretta Cohn:

"How did they get editorial note?"

Chris Erwin:

Yeah, was this a client email or internal?

Gretta Cohn:

No, it's internal. I have a big editorial note and here's why, and I know that you thought you were almost done, but it's going to be so much better because of this. And typically as a group, we come to that agreement very quickly that it's going to be better and our goal is to make work that sounds very, very good.

Chris Erwin:

I think that's how you build a great company and also become successful and are fulfilled in that. Like yesterday's win or yesterday's excellence is today's baseline and you just keep upping the threshold. My team calls me out for doing that all the time, but I always say, "Yeah, I hired you guys because men and women, you're incredible and I'm going to hold you big." And that makes for a fun work environment. And it's all in our mutual best interests. So I like hearing you say that Gretta and you just talked about celebrating wins often. What is like a recent win that you guys celebrated, big or small?

Gretta Cohn:

I mean, earlier today we recorded an interview where the host was in a studio in DC, our guests was in her home under a blanket fort in New Jersey. We had a little bit of a technical mishap before it started. One of the newer producers on our team was managing that. And I know that that could have been a situation where she got so stressed out that she could have been paralyzed by the overwhelming sort of urgency of overcoming this technical mishap, but she was calm and she kept us informed of what she was doing and she figured it out and the interview started late and it went long, but that was fine. And you got to give someone a thumbs up for that. Like that was hard and you figured it out.

Gretta Cohn:

And another recent win is we are about to launch season two of our podcast, Rebel Eaters Club and we have a promotions team working for us this time, we're making new artwork and we've got the episodes of the season in production. It's just exciting for me when all the pieces start to come together and we're like a month away from launch and it's not done and it will get done. But right now it's just this like ball of energy and that feels very exciting.

Chris Erwin:

This is your first owned and operated podcast where-

Gretta Cohn:

Yes.

Chris Erwin:

... your business has helped create audio stories for a variety of different brands and marketers and publishers and now you're investing in your own IP, which is really exciting. And so what is the general concept of Rebel Eaters Club for people who want to check it out?

Gretta Cohn:

Rebel Eaters Club is a podcast about breaking up with diet culture.

Chris Erwin:

Ooh.

Gretta Cohn:

Yeah. Our host is, her name is Virgie Tovar, and she's sort of one of the leading voices on breaking up with diet culture because it's extremely harmful. It is a huge industry. It's a debilitating thing that is, fat discrimination is something that's like not very often discussed, but such a huge sort of point of discrimination in our culture. And I have learned so much from this podcast, it's funny, it's a weird, there's a lot of eating of snacks. Our new season is in part a sort of cultural history of food, which speaks very much to my American studies heart. Like one episode is a little bit of like a social history of home economics, another talks about that sort of origins and evolutions of potato chips. So it's really like a celebration of body positivity. It's a celebration of enjoying food and enjoying what we eat and enjoying our bodies.

Gretta Cohn:

And I couldn't be more proud of our first original show being this show. Last year, I decided that the next push for Transmitter would be to really start to make original shows and to tip the balance of client work to originals. I think we'll always have client work and we love working with our clients, like right now, we were just working on a project with CNN and we're working with NBC and we continue to work with TED and love working on those projects. They often come with amazing hosts and incredible resources and access to really interesting places and people and stories. But for me, there's so much, I get a lot of joy and gratification out of the original shows where we control the narrative on everything. We need a new piece of artwork, I hire someone to make it and I sign off on it. Right. And it's really exciting. And so we have the goal for next year is to add several more original shows and we're sort of well on our way to that.

Chris Erwin:

I love that. You guys are bootstrapped, right? Starting with your $7,000 of savings, you have not raised any outside capital, but you funded the business by your agency work, what you guys like to do, it builds your brand, it also gets you paid and you learn from it. You're not investing in originals maybe as fast as like a Gimlet or a Ringer before their exits, but you and the team own a hundred percent of the company and you're building slowly and what could also last for a lifetime. I look at that approach as what we're doing also at RockWater as well, which is, yeah, we do a lot of client advisory. Haven't raised any outside money nor would it makes sense, but launching a podcast, launching newsletters, and it takes a lot of time and it goes slower than if you had a lot of funding, but you're building something special that has a different ownership stake, and it feels really good. So kudos to you.

Chris Erwin:

And I'll call this out. We're going to wrap up the Transmitter and move on to the rapid fire to close it up, before we do I give you kudos where in working with one of our clients, FilmNation, as they are building out their audio slate. I think I'd been connected to you a few years ago through Adam Sachs, a mutual friend and as we were talking to different podcast producers, we put you in touch with FilmNation and you created great work in doing hypothetical for them, for Luminary. And when you speak about just like your focus and emphasis on quality and always pushing the envelope, I think that very much came out in that format. And so kudos to you guys for doing such great work and making us look good.

Gretta Cohn:

Thank you. Yeah, we loved working with FilmNation. They're great.

Chris Erwin:

They're awesome. Milan and Alyssa and the whole team over there. They're just fantastic. The close out the Transmitter Media story, where's the audio industry headed and what role does Transmitter want to play in that? What are just like a couple of beats or points that stand out to you?

Gretta Cohn:

I think that we're going to see more well-produced audio fiction. I think that that's a space that's still in development and I think that there are a few really stand out examples of audio fiction that feels like watching a film. And I'm really interested in that direction, I'm really interested in seeing what people do and I'm very interested in participating in it. So that's one thing that I'm really looking forward to. I'm curious, I don't have like a prediction for this, but I'm really, really curious to see what all of these continuing sort of acquisitions and consolidations lead to. Right. Like I saw a tweet right before this about Amazon is seriously considering buying Wondery who had put themselves up for sale in a few weeks ago. So who knows what will happen by the time this podcast comes out? But I think it's just really interesting to sort of see the consolidation that's happening. I'm good friends with folks who have had their shops acquired over the last few years or are in joint ventures.

Gretta Cohn:

And I'm just interested to understand like, how do those relationships, how does that flow of money, how do those sort of desires that are set by the acquiring organizations, like what is that going to lead to? Like what are we going to see more of? What are we going to see less of? I'm just sort of have my eyes open about that.

Chris Erwin:

The amount of M&A activity has been wild, right? Like Spotify I think the biggest purchase recently was Megaphone, but having bought Gimlet and Parcast and Anchor before that, and then the purchase of The Ringer and then Entercom with Pineapple Street and Cadence13, I believe. So there's just like the amount of dollars that are flowing in. And even the bigger rights deals where it's Spotify and Joe Rogan and then not yet finalized, but Howard Stern's Sirius. So I agree with you curious to how it all shakes out and what it means for the smaller midsize players and those who are, maybe are not aggressively capitalized and what it means for the different types of content formats that will emerge in the future and how audio will start playing a role with also like the big streaming wars. We think about this a lot, like what is podcasting for Netflix and for promoting Paramount Plus and HBO Max.

Chris Erwin:

One thing that we've been writing about is the proliferation of smart speakers and at-home audio where a lot of radio and podcasting was made for commuting and people that are on the go outside their home, but now with COVID plus the proliferation of smart speakers where they're going to overtake wearables, I think they already did just this year, 640 million smart speakers forecast by 2024. What is smart speaker micro cast content going to look like? That's personalized, that's interactive and short form. Who knows? I think it's very exciting, right? So we are now down to the rapid fire and the end of the program. So the rules are simple, about six questions and you can answer in just a couple of words or a couple of short sentences, but they're meant to be quick and from the gut, are you ready?

Gretta Cohn:

Yeah.

Chris Erwin:

Proudest life moment?

Gretta Cohn:

This is hard. Proudest life moment? Oh my God.

Chris Erwin:

Or proudest Transmitter moment?

Gretta Cohn:

I can say that my proudest life moment thus far is probably what I've built with Transmitter. I could say, like I was thinking like, "Oh, this performance with Cursive or this big move that I made." But I think that making the decision to start Transmitter is probably my proudest life moment so far.

Chris Erwin:

What do you want to do less of in 2021?

Gretta Cohn:

In 2021 I want to look at Twitter less.

Chris Erwin:

Okay. What do you want to do more of in 2021?

Gretta Cohn:

Take more along walks in the woods with my dog and teach her tricks.

Chris Erwin:

I love that. I think walks are the absolute highlight of the day when you can get them in.

Gretta Cohn:

I agree.

Chris Erwin:

What one to two things drive your success?

Gretta Cohn:

I think I have a really strong work ethic that I got from my mom. She showed her work, like she was working... She worked a lot and she cared a lot and she sort of showed us what work ethic is. My interest and real desire to make beautiful things. I want to make work that's beautiful, that resonates with people, that they connect with.

Chris Erwin:

Got it.

Gretta Cohn:

And I care about the people I work with a lot. And I'm interested in exploring and have been exploring over the last three and a half years with the Transmitter what less hierarchical company structure and culture can be.

Chris Erwin:

Final rapid fire three questions, quick answers.

Gretta Cohn:

My answers are too long.

Chris Erwin:

It's okay. You'll make these short. Advice for media and audio execs going into 2021?

Gretta Cohn:

These are hard.

Chris Erwin:

Just whatever comes to mind. This doesn't have to be perfect. Like other people have said follow the money.

Gretta Cohn:

Don't follow the money.

Chris Erwin:

Don't follow the money. Any future startup ambitions other than Transmitter?

Gretta Cohn:

Nope, not right now.

Chris Erwin:

Here's an easy one. How can people get in contact with you Gretta?

Gretta Cohn:

Go to the Transmitter website, transmitter.fm. And we have an email address where anyone can reach out to us there.

Chris Erwin:

Awesome.

Gretta Cohn:

And you can follow me on Twitter where I don't post much, but I lurk a lot.

Chris Erwin:

Yeah, you are watching on Twitter for sure. Well, cool. Gretta, this has been a delight. Thank you for being on the podcast. This was fun.

Gretta Cohn:

Thank you. This was really fun.

Chris Erwin:

Talking to Gretta who is just so kind and warm hearted and just cares so much about her craft just yet again reminds me of these special people that the podcasting industry attracts and they are such a delight to be around. And I'm just really excited for the industry that they are going to build, which is just still so nascent. 

All right. Before wrapping up, just another quick reminder that we are hosting our livestream media and commerce conference that's coming up in the second quarter of this year and we're to have some great speakers, panels and keynotes. We're looking for more people to get involved. If you're interested just shoot us a note at [email protected]. All right, that's it, everybody. Thanks again for listening.

Chris Erwin:

The Come Up is written and hosted by me, Chris Erwin, and is a production of RockWater Industries. Please rate and review this show on Apple podcast and remember to subscribe wherever you listen to our show. And if you really dig us, feel free to forward The Come Up to a friend. 

You can sign up for our company newsletter at wearerockwater.com/newsletter. And you can follow us on Twitter @TCUpod. The Come Up is engineered by Daniel Tureck, music is by Devon Bryant, logo and branding is by Kevin Zazzali. And special thanks to Andrew Cohen and Sean Diep from the RockWater team.

Mike Gaston is the President of Stage TEN Studios, and a creative and social provocateur known for "programming between the lines". We discuss launching a profitable poetry press and soon after declaring personal banktuptcy, selling his first music video to MTV, founding viral digital studio Cut.com, and how he’ll shape the future of livestream media. 

Subscribe to our newsletter. We explore the intersection of media, technology, and commerce: sign-up link

Learn more about our market research and executive advisory: RockWater website

Follow The Come Up on Twitter: @TCUpod

Email us: [email protected]

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EPISODE TRANSCRIPT:

Chris Erwin:

Hi, I'm Chris Erwin. Welcome to The Come Up, a podcast that interviews entrepreneurs and leaders.

Mike Gaston:

This is going to sound insane. And I'm going to share this, but my thought was, is it possible to rob a bank and not go to jail? I'm like 19. Now when I'm thinking this way. And then I thought, yeah, I'll just take out a bunch of money on credit cards and then claim bankruptcy. And so like I took on all these credit cards and then I've just started traveling the world in a way that was just absurd.

Chris Erwin:

This week's episode features Mike Gaston, the President of Stage Ten Studios. Mike is a creative savant, who's known for programming between the lines. He had breakout success when he founded a viral digital studio, cut.com whose first video was about Grandmas Smoking Weed. You see, Mike is the ultimate provocateur, and he's been conducting social experiments since an early age. Like when just 20 years old, Mike launched a profitable poetry mag while apprenticing for an Irish poet. And then intentionally went into personal bankruptcy. Or when he created a music video for a friend's band, just for fun and ended up selling it to MTV. In Mike's current role at Stage Ten, he'll shape the future of live stream media. He talks about his recent work as well as some of his creative side projects at the end of our chat. All right, let's get into it. Mike, thank you for being on The Come Up podcast. So let's talk about where you grew up. What was your household like? What was your parental situation? Tell me.

Mike Gaston:

I grew up in West Seattle and my mom is an immigrant. She's from the Philippines. She didn't become a citizen until two years after I was born. And my whole family actually immigrated from the Philippines. So all my aunts, my uncles, my grandparents, my cousins, they're all here. And so had that very large Filipino side of the family around me. And then my dad, he's a white dude and he had a very small family that the only people I really got to know were my grandparents and then his brother and my cousin. But we weren't terribly close to them. And so the family was interesting. I had a bunch of essentially under five foot tall Filipinos about. So culturally, everything that I perceive was very much from a Filipino-American experience and not from the experience that my dad had. There wasn't a very strong kind of like a family philosophy or perspective from their side. But from my mom's side, my Filipino side, it was very strong. It pretty much informs everything that I think about today.

Chris Erwin:

When you mentioned that there was these the strong Filipino identity and cultural values, what were some of those that you remember growing up.

Mike Gaston:

Family is primary. It's also a very... It's a matriarchal culture. It's funny to say that because you look at authoritarians like Duterte, who actually is leading the country right now. And you're like, Oh, that seems very macho. And that's true. But it's really the women that do things like handle the finances.

Chris Erwin:

Interesting.

Mike Gaston:

And are really leading the family. And it's very common to never move out of the house, to live there forever and then your parents die and then you just take over the home. And so it's a very tight knit family structure, that's one. And then the second thing, which kind of I experienced growing up and then moved out of was this sort of mystical form of Catholicism. In Filipino culture, I felt like my grandmother practiced a magical form of Catholicism where it was like, everything was steeped in sort of miracles and possibility, right? I mean, this is a country where they crucify people, literally crucify people as part of holiday rituals in certain parts of the country. And so it's this sort of magical realism idea when it comes to religion. And that informed a lot of my early childhood.

Chris Erwin:

And when you say it informed a lot of your early childhood, because I'm also thinking to where you are today, which we'll get into, this like visionary in the media space and a point of view of the responsibility of creators. But what seeds was that planting in you at an early age?

Mike Gaston:

Honestly story. So I was fascinated by the stories that my grandparents would tell me and my mother would tell me. It was interesting because my dad converted to Catholicism as part of his wooing of my courtship of my mother. And he was never, I would call him a believer. I kind of think most Catholics are, it's very much like a more bureaucratic than it is like a belief to him. Whereas the Filipinos and my family is very strong believers in that kind of thing. And I remember as I was growing up, we would go to church every Sunday. And then right after church, we would go to the movies. And at some point, I want to say, when I was around eight or nine, I somehow convinced my parents that we should stop going to church and only go to the movies, which is probably why I make videos now. And I'm not a priest.

Mike Gaston:

But it's just something, there's some weird connection that was happening there between this religious communal experience that I was having in church. And then the kind that you have in a dark theater, staring at a screen with a bunch of people experiencing different states of emotional catharsis, right? Somehow I attached a more profound meaning to my experience with movies than I did with my experience in the church.

Chris Erwin:

And as you matured, maybe your sense of, Oh, I have to go to church to have the theater experience. And then you realize, and I think there's some parts of this story that will come out even more later, I don't need the church. I can just go right to the theater. And I think that comes up about you thinking about some of your coursework in school and saying, "Well, some of this coursework is great and some of it is not, I don't need it."

Mike Gaston:

Yeah. That just general sort of obnoxiousness definitely found its way into my schoolwork too.

Chris Erwin:

And so thinking also about your character as you kind of grew up and as a teenager and going to high school before you went off to college, reading some of your blog posts, you described yourself as a scared of everything extrovert. Tell me a little bit more about that.

Mike Gaston:

I've pretty much always been comfortable in social situations. I don't mind meeting new people, although it does have a tendency to impact me energy-wise. But any new scenario that I was in would instantly hit me with a kind of anxiety. There's just sort of a discomfort that comes with suddenly being presented into a new situation. Anytime I had to meet new people, initially, I would be kind of really timid about it. I was sort of in a corner, kind of a bit of a wallflower until I got acclimated to the temperature of the room. And then suddenly I was in the center in some way. And maybe it was certain aspects of my family life or in the early days we moved a bit around. There was so much attention from my mother's side of the family that I felt always like there's a spotlight on me.

Mike Gaston:

And so that made me kind of shrink into myself. So I would be freaked out a lot about different scenarios that I would be put into. But at the same time, once I got again, acclimated to the temperature, it wouldn't be tough for me to perform suddenly. But yeah, initially I would be freaked out by a lot of things, pretty often actually.

Chris Erwin:

Did you feel that people sought your attention or sought to interact with you? Because I look at you now and people seek you out for, they want to hear your point of view. They want to hear you speak, at conferences, at summits and for you to attend their events, but you don't always immediately engage. And so curious, going back, did you feel that social groups were like, "Hey, this is an interesting guy. We want to interact with him." Or did that attention not exist?

Mike Gaston:

So this is strange given it feels like a backdoor brag, but it's not intentional. I was friends growing up, I could be friends with literally anybody, with all the different kids. But I was popular among the popular kids, but I wasn't necessarily a popular kid because I didn't behave like a popular kid. I didn't behave in a way where I was seeing differentiation between me and other kids. So I was friends with a lot of kids. And then for some reason I would end up popular among the popular kids. I think maybe it's, I just knew from very early age, I would ask myself what I wanted. And then I would only just do the things that I wanted. And I think that that creates a gravity that people are attracted to because I think a lot of people don't ask themselves what they want or are uncertain about going after the things that they want. And so it's attractive when you see it in other people.

Chris Erwin:

So what did you want back then? Like in your teenage years.

Mike Gaston:

I wanted you to know why, why we did any of the things that we had to do. So I want to say when I was about 12, I became friends with this kid named Jorge Morales he was a really smart dude. The things that he would read was far beyond what everybody else was reading. He was a multi instrument kind of like musician. And he was unpretentious about all the things that he was really interested in, but he seemed so brilliant. And he was the one who introduced me to philosophical thinking in different types of philosophies. And so as a result of that, I instantly became, over the course of that year of seventh grade, I would say, I became really introspective, really reflective. And then what happens as a result of that is I was just suddenly in a question state where I was just trying to understand what are the things that I wanted?

Mike Gaston:

And I was trying to understand the why's behind the decisions that people were making, especially when you're a child, right? When you're a child, you're subject to what other people want of you, right. You have very little agency over the things that you want.

Chris Erwin:

Yes.

Mike Gaston:

And when you become a teenager is when most of that conflict starts to kind of arise. And it's because you're starting to feel your own agency, it's in a conflict with your parents' and their expectations. Well, that happened way earlier for me, that happened before high school. And that's largely because I was asking those questions all the time of what do I want, why do I need to do any of these things? And that became a lot more a macro sort of philosophical point of view for me going on. Before that, before I had discovered philosophy is more tactical, things would come to me and then I would just question it. I had a natural sort of questioning sort of personality. And again, I think there's a thing that happens with kids where you're told so often, your life is so prescribed to you that you're kind of go on a track. You do the things and you don't even know why you're doing any of the things. You're just doing it because that's the expectation. And I was never like that. I was always asking questions my whole life.

Chris Erwin:

This manifests in a story about your coursework in high school, you rejected one of your courses, tell me about that.

Mike Gaston:

Yeah. This was actually happened in seventh grade. This is actually before high school. But as I was asking those questions, I started thinking about... My mother again is Filipino and there's that cliché, the Asian tiger mom is not a cliche. That's just real to me. So she was very aggressive with my education, well, before I even got into kindergarten. So I was reading at three and I was writing full on essays before I got into kindergarten. And so by the time I was in kindergarten, everything was slow. Everything was crazy slow to me. Because for her, she was always trying to get me ahead. She wanted me to go to the best high schools, go to the best college, have the best job. And I remember around some of, when I was starting to have like a larger sense of myself and a larger sense of applying this questioning sort of personality but to my entire life.

Mike Gaston:

I started asking why I had to do any of these things, why do I have to get A's in all these classes? And so then I just started reshaping my world with experiments. And so I was like, "Okay, well, what if I just got A's in everything except this class that I don't really like." And that class was a religion class. Because I was going to private school. And I was like, I've been studying religion for eight years now. I'm in seventh grade. I had gone to Sunday school before I was even in kindergarten. This all feels really repetitive to me. How about this? I'm just going to do the tests. I got a D in that class. I do great on the test. And then I would just not do any work.

Chris Erwin:

How did that feel to get a D because you probably had excelled in school?

Mike Gaston:

Satisfying.

Chris Erwin:

Satisfying, okay.

Mike Gaston:

It felt liberating to get a D.

Chris Erwin:

Which probably frustrated your parents who were like, "Oh, you should be disappointed." And they're seeing you elated.

Mike Gaston:

Oh, yeah. My mom was very unhappy because she was like, "This is easy. Why are you going to getting a D?" This is the class that everyone gets an A in, why are you getting a D in this class? And I was like, "Well, if everyone gets an A and it's clear that I can get A's, why do I need to do that for this class? Well, what is the purpose of this?" And then she would say things like, "You're jeopardizing your chance again to a good high school." And I was like, "Well, then what happens after that?" If I get into a good high school, then it's about a good college and it's about a good job and then I die. I was literally, I would just go to the end of everything. What is the end effect of literally everything that is to that moment.

Mike Gaston:

And then I was like, "This doesn't seem like a track I want to be on." And my dad, again, because he was more transactional about his relationship with religion. I remember driving with him in the car and he was like, "Yeah. So you got a D." And I go, "Yeah." He's like... He just turned to me, he's like, "Whatever." He's like, "It's not a big deal." And I'm like, "Exactly." It was this moment where I was like, "It isn't a big deal." And so it became a thing where I had started to seek out moments of failure because I wanted to experience it. I wanted to experience what it was like to not meet my own expectations or meet my parents or meet anybody else's. But the way I started to approach it was different. In that instance, it was me not doing things that I knew I had to do in order to achieve something.

Mike Gaston:

And what it became was I started to seek out failure by doing things that were much harder and it felt impossible. And it was like, well, I'm just going to do this thing and then try and then get comfortable with that feeling.

Chris Erwin:

Yeah. It feels like you're a provocateur where there's the societal and cultural foundations. And you're like, if I poke at this crack, does that destabilize anything? And if so, does it actually change my life in a meaningful way or not, or change the end state in a meaningful way. And I think it's a very fast way to learn to provoke.

Mike Gaston:

It absolutely is. It was one of those things where I was just trying to find the boundaries to, everyone has a shape to their life. And it's one that they construct for themselves because we're all kind of editing our lives on our own. And I was like, what is the boundaries to this thing? What could it actually look like? What if I just started doing these things and stopped doing these things, or I start doing these things and stop doing these. Do any of these things matter? We invest meaning in so many, of the things that we're doing. And I was kind of in a constant state of questioning that. And just asking why.

Chris Erwin:

From there, there is a traditional path that does take place in the beginning of your career. You go to the University of Washington, and then from there, you end up at Boeing, a big company. So I'm curious to hear, just touching on University of Washington. What were the intentions there?

Mike Gaston:

Actually, out of high school, I didn't want to go to college at all. My plan was to go on a walkabout, but my mom was so disappointed with the idea that she had invested so much of her personal identity into my future success as an academic that I had to go to college, that I actually went to Seattle University for a year. And while I was at Seattle University, my grandfather, my white grandfather, my dad's father, he was in the midst of dying from diabetes and they had no help. So after school and before school, I would go to his house and I would help him. I would help my grandmother, I would help take him to the bathroom. I would help shower him, wipe his ass. He was literally... He couldn't walk, he couldn't... He was blind, had no feeling in the left side of his body.

Mike Gaston:

And he was literally falling apart. And I was the most depressed I'd ever been just like sort of a witnessing this and being a part of it. And I told him one day, I was like, "I got to leave, man. I can't be... I'm not happy in school. Because I don't want to be in school right now. And I can't do this." And he's like, "Yes, you need to leave." And I was like, "I'm just going to leave." So then I just started leaving the country and then I left the country for awhile and I didn't return for a couple of years. And then when I finally returned, that's when I went to UDaB.

Chris Erwin:

So when you were leaving the country, were you enrolled in any academic programs or no?

Mike Gaston:

No. I just left. So I would travel around Europe and I would meet up with friends in Mexico, in different countries. And then I found a mentor and apprenticed with him in Ireland, lived on his farm on the Southwest Peninsula and just study poetry. So I actually met him when I did a study abroad in Ireland. It was like a two week study abroad program. And he was a professor on that program and he was an Irish poet who had been born in Boston. So he had like dual citizenship. And then he would occasionally go and teach at Wesleyan University. And when I was traveling around, I ended up on his doorstep and I was like, "Hey, is it cool if I hang out here for a bit?" And then a bit turned into well over a year.

Chris Erwin:

So you lived on the farm?

Mike Gaston:

I lived on the farm and I was so broke. I would have to fish for food every day on the beach. And he was broke as hell too. Because he was... I mean, he's a poet. There's this thing about John? His name was John O'Leary. He was so broke. I remember when creditors would call him and they would demand he pay for bills. One of the last times I was there, he goes, his response to them was, "Now here's the thing. I'm going to tell you what I tell every creditor, I have a fishbowl and in the fishbowl are all my bills. Every month I put them in there. And then once a month I dip my hand into the fishbowl, I twirled it around and I pull out a bill and that is the bill that I pay for. Now, if you keep calling me, I'm going to put you out of the game." And then he just would hang up on them. He was a total character. He was a total character.

Mike Gaston:

He was such a wonderful weirdo. He looked a little bit like Walt Whitman's corpse on acid, incredibly skinny with crazy wild hair and that kind of thing. And and he was brilliant. He was the type of guy you could start reading from The Unabridged Shakespeare. And then he could just pick up without looking at it.

Chris Erwin:

It must have been, despite living in near poverty, having to fish for food every day, a very special experience, because I believe that you try to start your own poetry, newsletter or business, knowing you having experience of how difficult the business model is. And you did end up in bankruptcy, but you did it anyway. Because you're like this felt right.

Mike Gaston:

I don't know what happened like it. Part of my leaving the country a lot, initially when I was leaving the country a lot, I would do it in that sort of romantic nomadic kind of way that everyone who reads Jack Kerouac on the road kind of does where they go out and they're like, "Okay, I'm going to sleep with homeless people in the Gare de Lyon, and I'm going to eat nothing, but like baguettes because it's cheap and really cheap wine or whatever. And I'm going to try like hop on trades and then get off before anyone tries to get me to buy anything." And that gets real old, real fast. After the first many months of doing that, I kind of cracked, so this is getting to the bankruptcy, but what happened was I had a thought to myself and this is going to sound insane.

Mike Gaston:

And that I'm going to share this, but my thought was, is it possible to rob a bank and not go to jail? So this is, I'm like 19 now when I'm thinking this way. And then I thought, yeah, I'll just take out a bunch of money on credit cards and then claim bankruptcy. And so what I did, that's literally what I did. I took...

Chris Erwin:

Legal robbing, yes.

Mike Gaston:

That was legal robbing. And it was one of those things where I was just like, why not? And so I took out all these credit cards and then I just started traveling the world in a way that was just absurd. I didn't have luggage with me. I just had a Jansport backpack. And then if I needed clothes, I would buy it. I would stay at really nice hotels instead of the hostels that I was sort of surviving in. And then when people asked what I did, I would say things like, have you ever seen Doogie Howser? And they go, "Yeah." And I'm like, "I'm not saying the show is about me." And then I would just let it hang. And then I got to a point where I was broke and that's when I was living with the poet. And I was like, now I have to survive by fishing for food. And I had a little bit left over towards the end of my journey there with John.

Mike Gaston:

I was like, "I'm going to start a poetry press." And that's what I did. And I started this poetry press. And at first, it actually made money. It actually made money. And it's because I would find people like John who actually had a really great following and sell the books at these readings and I would set up tours. And I actually created kind of an independent bookstore distribution.

Chris Erwin:

Is this in the United States or is this in Europe?

Mike Gaston:

Both. Where I would do things in the United States and Europe.

Chris Erwin:

Wow.

Mike Gaston:

So the books would be in Shakespeare and Company in Paris and they would be in City Lights bookstores in San Francisco. And I would get it in all these places.

Chris Erwin:

How old were you?

Mike Gaston:

I was 20. It was kind of crazy because the more I would do things, the more people would buy into it. And so it came to a point where I had professors in all these different institutions hitting me up to publish their work because I was publishing really legit poetry by people that I had met in Europe and different things. And so suddenly they were like, "Well, this guy he's publishing stuff." And so it was very easy for me to find people whose work was actually meaningful within these circles. And I'm 20 and I don't know what the hell I'm doing. I'm just sort of doing it. And then I started going a little bit too crazy and started publishing people who literally didn't have any audience, but I just really appreciated their work. I want to say the first two books were profitable. The next two books broke even, last four books, it was negative dollars in a big way. And that's when I claimed bankruptcy.

Chris Erwin:

Thinking back to your earlier childhood stories where you wanted to poke the foundation and see what happens when things fail, did you are pushing this business, like how hard can I push this?

Mike Gaston:

Definitely moments where I was like, "Where are the boundaries again in this scenario? Can I continue to publish books and make money here?" So there was some of that, but largely the desire was I just really respected those writers. And I wanted to see that work get created. Even if I knew that the likelihood of making money was low.

Chris Erwin:

Another parallel from your early years is rejecting the certain institutions or coursework, but then going to university and then you start to go in different paths and try different things out and travel and go live on a farm and write poetry and start a poetry business. And then you go to Boeing, more like a traditional path again. So how did you end up there?

Mike Gaston:

Okay. So I claimed bankruptcy and then I decided to go to University of Washington and finish up school. It was one of those instances where I no longer felt like I had to go to school. It was this choice I was making and it was okay. As long as it was a choice I was making. And once I graduated from there, I got into grad school. I was going to go study Shakespeare at St. Andrews in Scotland. My wife now, who was my girlfriend then, got into Cambridge to get her Master's in Philosophy and History. And I was dead broke. I mean, I had claimed bankruptcy a few years before then. I had been paying my way through college. I had taken on two jobs at one point. I would go to UPS very early in the morning, take classes, then work at a sub shop late at night to pay for everything.

Mike Gaston:

And so I was totally broke and she goes, "One of us should probably have a job." Right. And I go, "Well, you got into the better school. You go to Cambridge and then I'll go get a job." And I applied to Boeing as a joke. Both my parents were working at Boeing at the time. And I had told myself my entire life, I would never work there. But they were hiring. And so I showed up and I was the only one, I remember that it was like this mass sort of they were doing tons of interviews and it's because for years, Boeing had been doing layoffs. And so there's this giant gap between where they had a bunch of people who are about to retire and they had no middle career people because they had laid them all off. And so then they were trying to like backfill with a bunch of young people. And I was the only one who kind of didn't want a job there. And the only one not dressed like they were applying to be on the apprentice. And then I got hired.

Chris Erwin:

It's like office space, like the less interested you are, the more appealing of a candidate you become.

Mike Gaston:

So one thing I'll say, here's a little bit of a story when I was offered the job, I was so stunned that they offered me the job because I'm an English major, right. And at the time, I have been told over and over again was that business people get business degrees. And so I didn't think this was going to be a thing. And I remember they called me and they go, "We'd like to hire you for this position. This is their HR department." It was like $42,500 a year to start or something. And this was back in 2004, I think. And that's a lot of money to a person who's been broke, literally his entire life. And so, but my instinct in that moment was to push it and kind of fuck with it. And I go, "Well, that's great. I really appreciate the offer. But I'll be honest with you. When I took the interview, I had a different number in mind."

Mike Gaston:

I'm literally making all this up off the top of my head because I was just stunned they even called me and they're like, "What are you thinking?" I was like, "Well, I was thinking more like 50,000." And then they came back at like 45 or something like that. And I was like, "Okay." And then I took the job, but it was one of those things where I was just sort of making it up as I went along. And then when I met with my boss for the first time I asked him, I was like, "Why did you hire me?" And he goes, "Your poetry press." I was like, "Really? You mean the thing that utterly failed?" And he goes, "Yeah, absolutely." And I go, "Why?"

Mike Gaston:

And he goes, "You actually understand something about business that the majority of your colleagues who are new here don't because you actually ran a business where you actually had to create contracts, negotiate that with artists. And also with universities, you had to create a distribution system for your books. You had to literally create tours for your authors. You created a budget for yourself." It was one of those things where it was a... And I was like, "Dang, you're right." I actually did learn a lot just doing that.

Chris Erwin:

You're at Boeing, but then fast forward, because I want to start setting up the story about you founding Cut and your entertainment drift. You do pull the rip cord at Boeing in a pretty interesting way, that includes pushing the quote unquote red button. Tell us about quitting day and pushing the red button.

Mike Gaston:

So I was at Boeing for a few years and it became a thing where I was just generally unhappy. There was enough novel problems at Boeing that I'd be interested for awhile. But what made me unhappy was that, this leads to me quitting was that I remember my boss came to me one day and he goes, "Mike, we're having some serious problems with this specific type of part that I was responsible for." Right? I was responsible for a contract that was worth millions of dollars. And there was a specific part that was constantly getting damaged in the factory. And that was impacting everything. And I was like, "Well, let me go investigate that." And I didn't know what I was doing. So my instinct was to then go and essentially create, what I learned later was a lean initiative where I would bring in all these different people who were a part of this whole flow, this process flow in the factory and to understand what was happening.

Mike Gaston:

And during that, we discovered that where the damage was occurring, why it was happening and how to fix it. And then we created a proposal for fixing it. I got promoted. I was saving the company lots of money. Fantastic. Three months later, my boss came to me and he's like, "Mike, we have this problem that's happening in the factory." And I was like, "Oh, really weird. So let me go investigate." I went investigated it. And I told him, I go, "Glenn, I literally solved this several months ago." Oh you did? I'm like, "Yeah, dude, you promoted me." And I go, "Here's the proposal." He's like, "Oh, fantastic. This is great." And then he left, I would continue to do different work. And then several months later he came to me. He was like, "Mike, we're having this thing. That's happening in the factory."

Mike Gaston:

I was like, "What is going..." And then when I research, I go, "Glenn, several times now I've solved this. This happened probably four times. And I've felt like I was going insane." Finally, my counterpart on the vendor side of it and I were talking and he had originally been at Boeing and now he was working at this supplier and he's been in this industry for like 30 years. And he goes, "Mike, Mike, Mike, here's the thing, buddy. This is a problem within this airplane since it's been created. And it's over a decade now that they've had this problem. And the thing that you came up with is exactly the solution that a handful of us came up with almost a decade ago." I'm like, "Why am I still solving it?" And he was like, "It's the machine. This is like the inertia of a large machine, like a company like this, where people are changing."

Mike Gaston:

There's a lot of heuristic stuff in a company like this. And it's very easy for things to kind of fall through and for stuff to get ignored and he was like what happens is, "Every now and then there'll be a new young guy like you who comes in, who discovers the problem, will fix the problem. And then it doesn't get fixed or it'll be fixed for a little period of time, then it'll get broken again." And that was so insane to me that I had been spending a good, over a year now solving the same problem over and over again and it not being fixed. That was like, I have to get out of here.

Chris Erwin:

Yeah.

Mike Gaston:

I have to. I feel like I'm in a time loop and I need to leave, but I felt bad. I felt bad because my whole life I've been told that I'm like a quixotic temperamental creative. And that part of me getting a job at Boeing was also sort of like a proof point to Jenny, who's my wife's now family that I wasn't just a crazy romantic artist. I could hold down an actual job that people have. And so I was like, is there a way to get fired? That would be interesting. So I actually tried to get fired, but I made rules for myself for getting fired. I was like one, I have to continue to do my work and I have to do it well, that's one. But two, I can't do anything that would be obvious to get fired. I'm not going to do drugs at work, I'm not going to bring a gun to work. I'm not suddenly going to become like abusive towards people and those types of things. Is it possible to get fired just through non-sequitors?

Mike Gaston:

Just by being strange. So I would do things, I remember again, the vast majority of the workers at the time were these older white men. And I would do this because I would enter into the restroom. I would apply lipstick on my lips just to see how they would respond. I would busk in the hallways, like with a guitar, I would stand on my desk and rock out to Andrew W.K. Don't Stop Living In The Red. Now, mind you, I'm doing my work at the time. I'm still doing it and I'm doing it well. I'm just being strange. I would do things like I would go to different offices and sit in conference rooms and wait. And then people would show up and then I would run the meeting without telling anyone who I was.

Mike Gaston:

So I'd be like, "Okay, let's begin the meeting." And I would go, "Let's go around the room. Everyone tell me who you are, how long you've been at Boeing, what your position is." And then I'd point to people. And then they would tell me, and then I'd write notes and I had to assign action items and then I had to leave and I never see them again.

Chris Erwin:

It seems that you wanted immediate reaction. Because everything you had done in your prior life that you talked about was you do something and there's an immediate result.

Mike Gaston:

Yeah.

Chris Erwin:

You hire writers that are not popular. And then you start bankrupting the company, right. You reject coursework, you get a reaction from your mother. So at Boeing is you solve this problem. You're expecting them to be like, "Okay, great recognition." But more of, okay, things are now going to change. That's not happening. So you're like, okay, at this culture, you have to find ways to actually provoke and get reaction. So did you get the reaction that you wanted?

Mike Gaston:

No, the thing is there would be no reaction. I would do these things and I would get weird stares or things like that. But mostly people were afraid of me or it felt like that. It felt like there was a weird intimidation. And I think part of it is that when you're working in a company like Boeing also, there's a lot of rules. There's rules for literally everything. There's a million rules in they're called PROS, PROS. And there is a PRO for literally every decision that you have to make. And it became a thing where I would say I wanted to get something done and someone would say a PRO about why it couldn't be done. And I became so frustrated by that because I wanted to see things get fixed and changed and I want to see things improve that I just started making a PROS.

Mike Gaston:

So I would say something in a meeting, I'm like, "This is something that we have to do." And then someone goes, "Well, according to PRO5236, we can't do that for these reasons. I'm like, "Well, actually PRO2348 supersedes PRO5236 because it says that we have to do that. And the thing is no one reads the PROS, man. So I could say these things and then people will be like, "Oh, I guess we have to do it." And then I would get shit done. And it was one of those things where I was like, I have to kind of work outside the system to get things done. The way I quit ultimately was where I was like, "Gosh, I seem to keep doing well at my job and I'm not happy here. I'm just going to leave."

Mike Gaston:

And at Boeing, their internal intranet and it's called... I think it's called toll access. I can't remember. But there was a big red button on the intranet and it was a self terminate button where you press that button, you were self terminating. And I wrote one day I just press the button. And then I instantly got a call and it was from HR and they go, "Is this Michael Gaston?" Yes, this is. Okay. Well this is Boeing's HR. And we noticed that, did you press the self terminate button? I go, yep. Oh, do you want to self terminate? And I'm like, "That's why I pressed the button." And then they go, "You do realize that once this goes through, it's very hard to turn this around." And I go, "I don't want to turn around. I want to self terminate."

Mike Gaston:

And then they try to make an argument for why you should stick around. And I just told them that I wasn't interested and this went on for a very long time. And then eventually they got the hand and that's how I fired myself. I literally pressed the eject. Yeah. Right after... So I got married about a year or two years and still working at Boeing. And I was hanging out with a friend of mine who was at my wedding and he used to be in a band called Minus the Bear. And I told him one day I was like, "I got an idea for a music video." And he goes, "Great, but you've never made a music video." And I go, "Well, I'm going to make a music video anyways. And I'm just going to make it. And if you like it, great. And if not, no biggie."

Mike Gaston:

They were touring at the time. So it didn't matter. And then I went, I created a treatment for it and I hooked up with a friend of mine who was in the New York film industry, but then had moved to Seattle. And then he hooked me up with a really great director of photography. And I brought him over and we made this music video and then I gave it to the band and they all dug it and the label dug it and they showed it to MTV and MTV loved it. And they were like, "Yeah."

Chris Erwin:

Was the band in the video? Or was it just the-

Mike Gaston:

No.

Chris Erwin:

-Music and... Okay.

Mike Gaston:

Yeah, no, it was for a song called Throwin' Shapes. And it actually starred my wife and one of my good friends and they play these two kind of opposing basketball players who aren't actually playing basketball. They're fake playing basketball on the street. And then they battle. And then the label like, "Yeah, we want to buy this." And so I sold it to them and then it was on MTV. And I was like, why don't I just do this? Why don't I just make videos? Because the first thing I made went on MTV.

Chris Erwin:

And you had never created any videos prior to this?

Mike Gaston:

No, I'd love movies. I'd love videos. I grew up in a time where it seemed impossible because equipment is expensive and I didn't go to film school and it felt like outside my reach. But in that instant, I was just like, well, whatever, I'm just going to go make one. And I remember talking to my friend who was in the New York film industry and he would tell me all the things I couldn't do. And I was like, "Well, I'm just going to do them anyways." Right. And then we got it done. And he was like, "How did you do that? How did you..." And I was like, "Well, nothing's really impossible, right? You can pretty much do anything." The hardest thing to do is to decide that you're going to do it. And then you just do it.

Chris Erwin:

You just fast forward to an end state that you want. And you don't worry about, what are all the different structures or the normal ways for how people would achieve this. You're like, "I'm going to find a way, I'm creative and I'm going to talk to people and I'm going to get it done." And you did. So this starts what I described as you hit the red exit button and you start the entertainment drift. And you're at a few different companies for pretty short stints of time, like one to three years, CBS, Rogue Scholar, Stripes39 and then SFST. And I think some of these companies are related. So during this period tell me... It seems that you're seeking something out or wanting to learn something. What was going on during those years?

Mike Gaston:

Once I made the decision that I was going to leave Boeing and do videos, the next thing that occurred to me was that I don't know how to do videos, right? I had made a thing and I had sold it, but that... I wasn't suddenly invested with a ton of confidence and about how to do any of these things. And when I was discovering at that moment was actually what my voice was. I'd always wanted to be a writer and tell stories, but I was circling in on the types of stories I wanted to tell and the reasons behind it. But what was still kind of opaque to me was the hows, how to actually get it done. So then my instinct was to just do as many things as possible. I started working for free on a ton of different projects, just to understand how other people ran sets and shoots and then taking jobs at different places.

Mike Gaston:

It was part of that same kind of instinct. I read every book, I would take jobs, I was taking in inputs to synthesize my own kind of perspective on how I wanted to make anything. Right.

Chris Erwin:

You always had an output focused mind. So at these companies were you also having an impact?

Mike Gaston:

To some degree, the thing is part of the reason why I would leave was because I wasn't satisfied necessarily with the impact that I was making. I was having an impact, but it always felt too slow to me in some of these places where... Like CBS, one of the places I worked at was at CBS Radio Seattle, where I worked for a show called the Bob Rivers Show, which was a National talk show. And my job as the video production manager. And there was only so much that you can get done as a video guy at a radio show. And so even though I was having an impact, it wasn't super satisfying. And so then once Bob was moving on from his contract with CBS Radio Seattle, it was clear to me that I had to move on too. And that's when I went and started a nonprofit focused on the digital humanities called Rogue Scholar.

Mike Gaston:

And I did that and much like my poetry press, that was a no-profit company, made a significantly negative profit. And after doing that for a little over a year, I needed to make money. Again, and I took a job at Stripes39. And this one was interesting because Stripes39 was a startup in internet marketing. And it was the first place that I worked at where suddenly people would listen to me. The CEO would listen to what I was saying. And it was jarring. It was jarring because I had been so used to being kind of like feeling frustrated because I would point out all the things that need to be fixed and how I would fix it. And no one would listen. And finally, there was a guy who I remember telling him, this isn't how I would run a creative side of your company at all.

Mike Gaston:

And then he was like, "Really?" I go, "Yeah." And then he took me into a room and then spent three hours whiteboarding with me about how I would do it. And then he basically was like, "Go and do that." I was stunned. I was suddenly in an environment where people would listen to me and that changed everything. Number one, it made me a lot more circumspect about the things that I was saying. Suddenly when people are paying attention, you can't get away with the feeling like, "Oh man, I have all these great ideas and no one's listening." Suddenly you have to really examine are these ideas great at all? Because they are listening.

Chris Erwin:

It's like, crutch to ready yourself for dismissal saying, "Oh, I can say all these big ideas, but no one's going to listen to me. So I'll just... Too bad for them. I'm just going to go on to the next thing and throw out some big ideas." And then all of a sudden they're saying, "No, Mike, this is great. Now do it." And so now this is a new muscle of execution responsibility. And you're getting what you wanted, be careful what you wish for.

Mike Gaston:

Absolutely, Boeing was formative because I learned a lot about how to create processes in a place and also to work within a large organization. And as much as I was a total brat, when it comes to things I was trying to get away with, I was still doing my job. I was still doing work. And I learned a lot there about project management and about moving things through something really bureaucratic. When I go to Stripes39, it's the exact opposite of Boeing, right? Boeing makes products that last for 40 plus years and that are heavily regulated. So they have nothing but red tape. Then you go to the internet and you're doing internet marketing. And these are for products that lasts for about 30 seconds, right. And then you have to make an entirely new thing. And then you're doing it in a startup where there's literally no process.

Mike Gaston:

And so one can be paralyzing because of the weight of the amount of buy in that you have to have. And the other one can be paralyzing because all there is, is opportunity with no checks and balances.

Chris Erwin:

It's chaos.

Mike Gaston:

And so it's like... It's chaos. And so there was an instance where I was like, "Whoa, people are paying attention." And then what happens is you level up way faster in a world like that because you have to. You suddenly have to be like, "Okay, the things I do have a real impact. So how do I make sure that I'm doing things that have a real impact and not just be the guy who's readying himself for, you said for dismissal, but the guy who knows, well, they're going to hold me to these things." So I actually have to execute on it.

Chris Erwin:

So you start executing against his vision and what happens?

Mike Gaston:

So the company ended up turning into a startup studio and they would incubate different business models and then invest in them and Salil, the president of the company early on, knew that he wanted to invest in video. And we got to talking and that's kind of where SFST came out of. He knew that you wanted to invest in video, but we didn't have a business model that we were committed to. So SFST was kind of essentially a creative studio. We were doing for other companies, what we had been doing up to that point for Stripes39, which is create content that would help those companies get to number one on Google. My task at the time was to create viral content for brands like InsuranceQuotes.org and Medical Billing and CodingCertification.net, which is like pushups. If you can make something go viral for a company like that, you can pretty much make it for anything.

Chris Erwin:

Say if the product or the company wasn't super appealing to you, did you enjoy the challenge of like, "I'm going to make you a really cool video."

Mike Gaston:

Always. To me, they were just interesting problems to solve. And again, this goes back to this belief that nothing is impossible. So it was fun. It was fun to think of these as exercises. Like, okay, well, how do I get this thing to go viral? How do I make this thing? And then every time we would make something, it would appear on like Gizmodo or some other large site. I feel like I'd won something.

Chris Erwin:

Yeah. But then it seems that you want to solve more things, but you need more time, more resources and focus to do that, which then seems to be a precursor to the co-founding of Cut.com. Tell me about that transition.

Mike Gaston:

So Cut was interesting. Because after a year of doing this sort of like creative work for other companies and in that first year we were profitable, but I was not happy. I wasn't happy having to do service work for other companies that I didn't feel really got it. And Salil wasn't happy because he wasn't interested in investing in a production or creative agency. When you're a startup studio, you're investing in products that you're hoping is going to scale to such a degree, that's going to become a billion dollar company. We were at an impasse about what we wanted to make. And I remember having a very specific conversation with him. He was friends with a guy named Matt Inman who created the Oatmeal. And then he created Exploding Kittens and has had massive success in translating his IP into actual products that people want to buy.

Mike Gaston:

And he would talk about Matt all the time. And I told Salil, I was like, "Listen, you would never invest in Matt, in reality. Matt could never do what he is doing now in your system because you have a very rigid perspective on how things get done." Salil is I think he's a very smart person. I think he's one of the most logical rational people that I met in this industry. And he has like a very specific framework for getting things done that make it difficult for, I think, outliers to exist in his world, which is funny for a guy who essentially creates companies that deal in vitality, right.

Chris Erwin:

Yeah.

Mike Gaston:

And I told him, you would never invest in a Matt, and I think that was a dare to him. Because he was like, "Well, what do you want to make?" I was like, "I think if we want to make a company that's focused on media, then it should be about making things that are premium because ultimately what's the point of doing videos, if you don't want them to be premium and actually have an impact on people." The way everyone is doing videos right now, does it make sense to me? And so I told him, I was like, "If you want predictable sources of revenue, don't make videos. Go be a plumber, go buy a bunch of funeral homes because people are always going to die." But for you doing videos, it doesn't make sense to try to eke out money for views through advertising. It's all diminishing returns.

Mike Gaston:

I'm like, "What you have to do is create content of such supreme intrinsic value to the audience that they end up paying for it or things related to it because it's part of their universe." And he was like, "Okay, go do that." You know, Salil he's a very much a prove it guy. So he was like, "Okay, prove it. I'll give you six months of runway." And at that time I was just like, I doubled down on that. I go, "If I can't make something that's going to go viral, that's going to speak to this editorial vision that I claim to have in a month, I don't need six months. I need a month to do it." Right. And he's like, "Okay." And then within a couple of weeks I made a video called Grandmas Smoking Weed for the first time. And then it seemed like every week after that, me and my co-founders Jason Hakala and Blaine Ludy, we would just keep making formats that would somehow hit the zeitgeists.

Mike Gaston:

And very quickly after that, we got a lot of interest from a bunch of different companies to invest in us or buy us. And then after that Salil largely trusted my vision for what I wanted to create and then gave me the runway for the rest of the year before I went out to go raise money from Comcast Ventures and Compounder and Sky.

Chris Erwin:

How did you feel with this success? Was it validating, was it exciting or was it also in a way, could it be interpreted as frustrating where it's like, Oh, maybe I didn't provoke or think bigger and maybe I got to change that. What was going through your head?

Mike Gaston:

It was validating, I had spent so much time sort of arguing for these things and then as we were doing it, it was like we were proving out exactly what I was saying. And then the attention was validating, but honestly, I wasn't worried about whether or not the vision was big enough. I was more concerned about how were we going to continue to keep executing against it. Right. I had created a model that was completely dependent on the idea that we could always create outliers.

Chris Erwin:

Yeah.

Mike Gaston:

And we were doing it and it was just a matter of like, okay, now how do I get to the next level? How do we scale this in some way? Another part of the model was this idea of use the internet as a place to kind of rapidly prototype formats, see if there's an audience and then find ways of leveraging that in some way. And that second part, the leveraging it, was a much harder thing to figure out than the first thing. I was kind of blown away at how our instinct for creating things that would spread was kind of on point, just about everything we were making was killing it. And then it was a question of like, Oh, shit, how do we actually exploit any of these things? Because everything that we're making is doing well, how do you prioritize how you want to then turn that into a revenue stream.

Chris Erwin:

Yeah.

Mike Gaston:

And that took a couple more years.

Chris Erwin:

And did you enjoy thinking through how do we scale this up and spending more time on that part of the business?

Mike Gaston:

At first, at first, yeah, because it's novel problems. The thing is it's really difficult to get bored in a startup because things are changing so fast, things are moving so quickly. And so every new thing was delightful until it stopped being delightful. When it stopped was when I took a step back and I started examining the things I was focused on and it occurred to me that for a couple of years now, I had stopped asking myself what I actually wanted. My whole life, I had been asking, what do I want, why am I doing this? Why is any of these things happening? I become a lot less reflective on that. And I, instead it was more like I was just solving problems. A problem would introduce itself to me and then I would figure it out and it would be novel and interesting. And then a new one would show up and then I would approach it like that.

Mike Gaston:

But then when I kind of like woke up for a minute and I looked at what I was doing and I thought is this even what I want anymore? And then I realized that it wasn't. And then I had been sort of distracting myself with the momentum that comes with a startup.

Chris Erwin:

A startup is all consuming. And then I think with the responsibilities of, I have a team, people that rely on me for employment, investors that are looking to me for return and premium of the capital they've given me, that responsibility you get lost in it. But it is clear that you have this ingrained code in you that is always asking what else or how can this be different? It's interesting to hear that you felt that, Hey, something's missing here. And it's the fact that you're not able to ask yourself these reflective questions. And I think it was when I first met you, I was reaching out to you on behalf of a client we were working with, I got to know you. I saw you at the YouTube summit. You came to some of our events.

Chris Erwin:

And I remember you said, "Chris, my role is changing. I was just a creative and now it's management and fundraising and I'm on this speaking tour." And I sensed that there was this inner turmoil where you weren't sure, you were like, "I guess this is like the path, I'm doing these new things because there's success here. But is this the success that I want? I'm not sure if this is for me."

Mike Gaston:

You're literally articulating exactly what was going on in my head, in terms of suddenly I had found myself on a track. Like the person that I thought I was, the person who was sort of like avoiding tracks, suddenly found himself on one.

Chris Erwin:

Yeah.

Mike Gaston:

And I'm like looking around being like, "Is this even what I want?" Everyone's telling me, this is what I should want. The company is successful. It's making money, it's profitable. We have all this traction. It seems like opportunity is everywhere. And at the same time, I'm like, "But is this even what I want?" And then I was like, "No, this isn't what I want. There's all these things that I don't like about this. And I don't want to perform this role anymore." It felt like I had solved something and it was no longer interesting to me to continue down the path because I could see where the end point was. There was like real existential crisis happening for more than a year before I eventually left the company.

Mike Gaston:

And people think all the time, they were like, "Well, you're the CEO of a company that you founded, shouldn't you be able to do whatever you want." I'm like, "No, that's not true. That's not true." When you're really the leader of a company, you're actually beholden to a whole lot of people. You're beholden to all the people that work for you, all the people that invest in you. And then all those tangential people who are around you also, who are kind of invested in your success. And so up to this point, my mom didn't know what I did, right. She did not understand anything. But she understands that there's a name of the company that I founded on a building. She understands that there's a lot of people who work there now for me, she understands that everything that I'm making is appearing on the news and various other things.

Mike Gaston:

And so it becomes a thing where everyone's so invested in this idea of success that you're creating. And you're like, "Ah, it's my job to prop this up. It's my job to continue to kind of keep this thing moving." And it felt like a trap.

Chris Erwin:

So I think I got a sense that you did start to act out a bit. Similarly to when you were at Boeing, I remember, I think I may have first met you in person at the YouTube summit in Venice and immediately thought you were a very smart guy, unique point of view, but you felt introverted. And I knew you were about to speak on stage. Wasn't sure if that energy was going to translate, but it definitely did.

Mike Gaston:

Thank you.

Chris Erwin:

And I think I remember you speaking, you approached the topic with a really unique point of view and everyone at the summit was talking about your talk after the fact. And then I think there was another talk that you gave at VidCon. I was not there for that. And I think you had been tasked with just talking about building a content business in the new digital economy. And I think the expectation was just talking about me, and I'm making it very tactical, but you commandeered the reins and you went in a very different direction talking about creator responsibility to the audience, to viewership.

Mike Gaston:

Yeah.

Chris Erwin:

And so it seems like, from these experiences that this inner turmoil was starting to come out of you, is that right? Do you agree with that?

Mike Gaston:

No. That's kind of right. I mean, I think there's a... I can't help it, honestly, I can't help. But yeah. I was telling this to Melinda Lee, who I work with at Stage TEN and I go, the difference between how she operates and how I operate is little, is different and neither is good nor bad. Although, maybe you could say that mine is flawed. Companies can be complicated, incredibly complicated and there could be tons of entanglements that make it difficult to get anything done. She is so effective because she knows how to create a path around and through entanglements to get to the thing that she is trying to get done. And I can do that. I can totally do it and I have done that, but I'm kind of like... It almost feels like a mental health issue.

Mike Gaston:

I can do that for a time, but when I hit a certain entanglement, my instinct isn't to try to find a way around it. My instinct is to literally untie the knots. It's to literally make them untangled. And that is, can be self-defeating, right. Because that's philosophical and foundational and is trying to really get everyone aligned in one way. And so when I would go and have these talks, I wasn't interested in doing the things that I knew, what are the best practices for a talk, right. Okay, I got to speak this quickly and I have to move around the stage and I have to you know, Gary V it up in some way, and I got to put it in very simple terms for people and it's got to be incredibly tactical and practical. And instead when I wanted to do was be more introspective and reflective around the why's and the wants that we all have when we're creating any of the things that we're creating.

Mike Gaston:

And try to give people some kind of framework for developing their own principles around it. That's really all... I was like, "I'm more interested in that." I'm not interested in optimizing this talk in a way that somehow gives me more credibility with this audience. All I'm interested in now is just articulating for them how I perceive things. And then maybe it strikes, or maybe it doesn't. I don't know.

Chris Erwin:

If you want to build a sustainable business model, instead of telling people, "Spend this much money on production, put out these types of videos that are optimized for X, that you can get programmatic and direct sales and also build out some DTC channels." What you're saying is that's just a bunch of tactical knots. And the way that we can really untangle this from the top is, here's how to have a creative vision. Here's the creativity that the world needs today. And if you focus on that, you will find success for yourself, for your team and for your audiences. So start bigger.

Mike Gaston:

Yeah. I literally walked them through the questions that I asked in order to then set out, making a company. Because the point is that if you give people a hundred best practices to deploy, then you actually haven't set them up for success. Because if everyone does those things, then all they're doing is competing with each other, which doesn't give you the traction you think it does, right? Like early days at Cut, I remember Salil who's the president Startup Studio. He wanted me to copy what Buzzfeed and Upworthy was doing. And I remember asking him why. And he goes, "Well, they have all the money. If they have all the money, that means they're hiring the data scientists and the technologists who are essentially creating the tools to help them to predict virality online. Our job is just to draft off their success because you're small and you can do that really quickly."

Mike Gaston:

And I said, "I don't know, in the history of anything where a smaller force has somehow defeated a larger force by copying the strategies and tactics of the larger force." It doesn't make any sense to do that. My point in some of those talks that I gave was to give people a path where they weren't actually competing with each other, they were competing to create relevance for the audience. Because that's the only thing that matters.

Chris Erwin:

I liked that because there's also a sentiment that all of you are special. All of you are very capable. Now find your own way and we can all win.

Mike Gaston:

No, it's absolutely is. I mean, again, this goes back to even raising money. I remember talking to Sam landman at Comcast Ventures. And initially he was like, "Mike, we're not investing in advertising plays." And I go, "This is great because why in God's name would I make a company that orbits something nobody likes." And he's like, "Well, I don't understand what are you making then." I go, "I'm going to make something of such intrinsic value that people are going to pay for it or things related to it." And I go, "I don't need to be Mark Zuckerberg. I don't need to consume the internet in a world where there are billions of people watching videos online every day, I need a million people giving me 10 bucks a month. Can I do that?"

Mike Gaston:

And that's the truth. If you're creating a media company, you don't need billions of views. You only need that, if you're making like 0.001 cent on every view. What you need is a cross section of people who are invested in your success because you are creating something of value for them. And so they were paying for it.

Chris Erwin:

You fire yourself, you write a blog post about it. And I want you to give us the summary. And then we're going to talk about what you're doing at Stage TEN. And we'll close with some rapid fire.

Mike Gaston:

At the end of last year, I became probably the most frustrated with my position. And there had been tension between the things I wanted to do and my board and mind you, my board is actually very... They're probably most flexible and adaptable board you can possibly think of. It's just the things I want to do were not the same as what they wanted. And so it came to a head where I was like, "Yeah, these are things that I need to happen or else maybe I should go." And then out of that, they're like, "Well, what if we did things like this? And could it look like that?" And I'm like, "Nah, I really can't. I got to go." And that was really tough because even though I had been wanting to leave for a while, for well over a year, once that became articulated and out in the world and manifested into an actual deadline for me leaving, I was maybe the most depressed I'd ever been in my entire life.

Mike Gaston:

I spent a good weekend sitting on the couch, staring off into space to the point where my wife goes, "Do I have to hospitalize you?" And it's because there's this tension. And the tension is between the things that you know that you want. And then all those expectations that had been building up over years around me, right? I had created something that existed and manifested itself out into the world and people confused it with me. People would see the company and it was me. And so it's like a weird sort of... It was like killing your ego. It's literally killing yourself to some degree where you're like, "I'm not going to divorce myself from this thing." And having to kind of like get that right in my head was a really difficult thing. As soon as it was announced to the rest of my team, as soon as I announced it to them, I felt more liberated than I ever have.

Chris Erwin:

Like cathartic. Yeah.

Mike Gaston:

Oh my God. Yeah. And it was funny because afterwards a bunch of them came up to me and they were like, "This was maybe the most Cut thing you could possibly do." The fact that you saw what was the end point of all this kind of thing? There is very much, like I was telling you before, there's this sort of archetype for an entrepreneur.

Chris Erwin:

Yeah.

Mike Gaston:

And it's all builds up into the sort of like a great man mythology and the fact that I had pulled the shoot on that and decided I'm not interested in pursuing those things. What was basically me living my brand that I created up to that point.

Chris Erwin:

It's a beautiful moment.

Mike Gaston:

Yeah. No, absolutely. And then I feel like my life changed after that in a really big way. Suddenly I could see opportunity again, in everything that I was doing. I no longer felt beholden to the stakeholders. There's so many things that I couldn't do as the CEO of the company either because there was an unwritten rule or because there was an actual rule in the agreement of taking on investment that prevented me from kind of stretching myself. I wasn't interested in optimizing the company I had created. I was more interested in kind of seeking out new experiences for myself.

Chris Erwin:

And I remember, I think we spoke like a month or two after you had left Cut. I think we did a Zoom call, wasn't in person. But I sensed, I was like, you feel lighter and you were talking about, I'm excited to... I want to try different things. And it seems like there was intent to play a bit more. I like that. Because I also think about one of the key brands that you created at Cut, which was HiHo and creating empathy through play for this kid's brand. And I was like, "Oh, Mike now gets to play a bit." You just visually and the way that you spoke, it was also very exciting for me to hear. Because I'm like, "I think he's going to go do a bunch of different stuff." And some of it's going to be maybe not so great, but some of it's going to be really incredible.

Chris Erwin:

And so I was closely tracking where's he going to go? And I find it interesting. So you chose to go to Stage TEN. I heard you say that there's very few people that you would bet on, but you would definitely bet on Dave Lazar. So tell me about the decision to join Stage TEN and why Dave is so special to you.

Mike Gaston:

So I met Dave at that YouTube publisher summit that you talk about and he was trying to sell live in a period where people were kind of over it. But he had been doing live and interactive as a thing for years before it was a fad with Facebook. And he's still doing it in a moment where suddenly people are realizing how important it is, right. And the reason why I bought into Dave is because he believes what he's talking about. Right? It's so often I'll meet with people who are very slick and very self produced. They have their story down, they've read what it means to be an entrepreneur. They know the jargon, they know how to make the thing.

Chris Erwin:

Yeah.

Mike Gaston:

It's rare that I meet people who are so incredibly passionate and believe so much in the vision of the thing that they want to do. And there's a lot of things that I could tell that they could use my help on, but it was one of those moments where I'm like, "He's a dark horse." There's potential here for radical success. And I don't mean that just in terms of money, because that's not that interesting to me. I meant that more in delivering on his vision. And I was like, "Man, I want to hang out with true believers. I want to hang out with people who are going to invest themselves completely in the thing that they're trying to make. And just because it's interesting for them and not because they think that they can just seek out a really easy exit." And that's the thing, that's the thing that ultimately drew me to doing it with him.

Mike Gaston:

And I told him all the things that I would need in order to work in a company like his and he gave it to me. And that included the freedom to work with other people and to create things on my own. And he understood that to continue to energize a creative, you have to give them space. You can't just like lock them in.

Chris Erwin:

Yeah. We're going to talk about, you're a man about town doing a few different things with American Public media and your imaginary beings, but quickly you are now the head of studios at Stage TEN. What does that mean? What do you work on? And then what is the bigger vision that you're building towards?

Mike Gaston:

Really the thing that I told Dave was he has this incredible platform that he's created for live and interactive content. The problem is that people in the industry have a low imagination. They can't do things unless they've been shown that it's going to be successful in some ways. So what's often happens is they adopt his technology in order to do the most pedestrian things possible. It's like, we're going to remake broadcasts, but it's going to be on the internet who cares about that? Right? That's not interesting at all, but they'll do it because it's a useful tool, it's convenient right now in COVID, right. So I was brought in to literally make the market show the kind of possibility there is in creating formats that are live and interactive for people and raise the imagination of the industry.

Mike Gaston:

So that means partnering with celebrities and brands and teaching them how to create really radical content that can have a huge impact on their fandom or their audiences. And some of the stuff I'm working on are pretty large. There's a project that I can't actually speak to right now because we're literally in the midst of it. But it's significant. It could be game-changing in terms of who we're trying to partner with and what we're trying to create. I'll share that with you as soon as it goes through. But like I said...

Chris Erwin:

Sorry, listeners, I'll try and bend Mike's arm after the interview see if we can get that out. But no, I'm excited to learn more.

Mike Gaston:

That's what I'm supposed to be doing.

Chris Erwin:

What were some of the projects that you've done to date? Were you part of John Krasinski and some good news? And I think you also did live with Cardi B.

Mike Gaston:

Sp I wasn't actually part of the John Krasinski one, that happened like right before I showed up. There's an incredibly talented director and producer at Stage TEN that as soon as I showed up, I was like, "Okay, you're not just a creative, you're the head of production." So she was the first person that I promoted at the company. And I've been working with her on a lot of the creative, I think she's brilliant. Her name is Sonia and Sonia, she's been integral in creating really incredible shows for Cardi B's launch of her WAP music video.

Chris Erwin:

Yeah.

Mike Gaston:

Or doing a live and interactive show with Jack Douglas on YouTube for YouTube Originals. I'll say that these are very successful people who everyone recognizes.

Chris Erwin:

I really like what you said about what are the formats that are going to happen in live stream media and commerce and that you Mike, you're going to make the market. It's so topical because this live stream media market is exploding. It's a place where my company is also spending more time writing more about, talking to more clients that want to build. And what we keep hearing is people are saying, "What is the IP that we can create and own that's going to win on." There's going to be like a proliferation of all these different livestream technology platforms outside of big tech incumbents. But if you have the good formats and IP and you partner with great celebrities, you could win everywhere. What does that look like? It's an interesting conversation because it's so wide open.

Chris Erwin:

It also makes it, for someone like me, who's not nearly as creative as you it's like, "Oh wait, where do I start?" Because I like looking for inspiration and frameworks, but for you that chaos and messiness, it just seems you have this incredible cauldron that you're going to drum up. So I just say this is, I'm very excited for what you're going to do and I will be tracking it closely and probably helping my clients better understand it.

Mike Gaston:

Oh dude, I'll send you some decks. I've been working on to kind of explain what I'm thinking internally at the company, because I'm not precious about any of that. I feel like it's a little bit like if you're going to open up a bar, you want to do it on a street with other bars. You don't want to do it in the middle of nowhere, right. I'm actually happy to talk about how we're thinking about it with everybody. Because the more people who are invested in live and interactive, the more potential it has to grow rapidly. So I'm happy to share that thinking after this.

Chris Erwin:

Well, I love that. And also as a great leader, it's that your process is special. So it's not like, Oh, you create one thing and then, Oh, I got to protect it. It's like, no, I'm going to create a bajillian different, amazing thing. So if I give you this, sure, I'm already onto the next.

Mike Gaston:

Yes. I mean, that's how I think all the time. I remember talking to Wolfgang Hammer, who's a friend of mine. He was the CEO of Super Deluxe. And now I think he's a head of movie development at Miramax and early days he was really trying to convince me to sell Cut to him or just to join him over at Super Deluxe. I remember asking him why. And he goes, "Well, Mike, everyone's copying your formats. And that means it's diminishing your brand because they're doing shitty jobs of it. And so you want to be..." And I was like, "Well, yeah, that would be a problem. If I thought the thing I give away for free was my product." And he was like, "What do you mean by that?" I go, the problem is in the digital media industry, people give away things for free and they think that's their product.

Chris Erwin:

Yeah.

Mike Gaston:

That's what they're good at. The thing is, this is just one thing. This is all just top of funnel marketing for me. The goal is to get an audience, to then buy into the thing that I'm going to charge them for. And that's going to be premium. And I'm like, "So all I have are endless ideas."

Chris Erwin:

Very well put. All right. So we'll close on this question before getting into rapid fire, we're actually going to move this rapid-fire question up. Typically, ask people any new startup ambitions are in front of you. You have the creative freedom to work on a few different things. And I think it includes also some work with Tom DiNapoli, who's a good mutual friend. And I think he's the reason why I first reached out to you. Tell me about some of the other projects you've got going on.

Mike Gaston:

After I left Cut my instinct was just to make all the things I wanted to make. There are games that I want to make, there are podcasts that I want to make, there are movies and videos and all that kind of stuff. And I was like, "I need a house for this stuff." And the more I thought about it, the more I'm like, "No, there is actually a company in here and it's one that's invested in innovation." Because I was like, in this moment, what's important is not to create, like you said, IP that you just fiercely defend all the time, because it's not possible in this moment. It's really about how do you create a process where you can innovate constantly. So I'm a big fan of this author named Jorge Luis Borges. And one of the things I'm really attracted to is one of the themes in his writing, which is the idea of artists and intellectuals essentially reshaping the world around them.

Mike Gaston:

He has this short story called Tlön, Uqbar, Orbis Tertius. And in it, he has a fictional version of self, discovers a reference to a country called Uqbar. And he's trying to understand where it's coming from. And more he learns that he discovers that Uqbar is a country on a planet called Tlön and that he learns that there is essentially a secret society of people who are essentially reshaping the world by referencing this fictional place in the world. And I thought there was something really beautiful about it. And another book he has is called Imaginary Beings. And in it, it's kind of like an encyclopedia of imaginary creatures. And I was like, I'm going to create a company called Imaginary Beings. And I'm going to invite all these really brilliant people that I know out in the world who are incredible creators and media professionals. And then we're going to do all the things that we're passionate about and believe in, without any of the anchors that weigh us down in this industry. And so that's the thing that I've been working on, on the side.

Chris Erwin:

It's interesting to hear how you answer these questions, because something... As I did some research, people were like get at what drives Mike's vision and purpose. And as you just always referenced like, Oh, well, this happened to me or read this. And so this now caused me to launch this. It just naturally comes out. And I think that you have so many different inputs and inspirations in everything that you do. It's like you're a polymath, someone who just has like poly interests all over the place. And can actually handle them and manage them and then kind of navigate them into some really interesting output. All right, let's get into the rapid fire. We'll close this out. In our rapid fire, can I have around six questions and short answers could just be one or two words or even just one to two sentences. You are empowered to be brief and concise.

Mike Gaston:

Okay. I'll try.

Chris Erwin:

I think constraints help you, proudest life moment.

Mike Gaston:

I'm not really a pride guy. I mean, it sounds not real, but I'm just not. I think the idea of finding a lot of deep pleasure and achievement is difficult for me because it's already over.

Chris Erwin:

What do you want to do less of in 2021?

Mike Gaston:

Doom scroll TikTok.

Chris Erwin:

Wait, what does doom scroll mean?

Mike Gaston:

It's where you're obsessed with sort of consuming all the negative news that's out there. You can't help it. And I just need to stop doom scrolling TikTok.

Chris Erwin:

Got it. What do you want to do more of in 2021?

Mike Gaston:

Write. And I don't mean long formal writing, which I've been doing, but my wife is very disciplined at journaling and I want to do that because I think it'll help me process this moment we're all living in a lot better.

Chris Erwin:

What would you do you say is one to two things that drive your success?

Mike Gaston:

Oh boy. Okay.

Chris Erwin:

Short answer.

Mike Gaston:

Nothing is impossible, right? So knowing that... One of the things I told my team early on was if Elon Musk who knew nothing about rockets could create a rocket company, then there's virtually nothing that's... Especially in videos, we can do whatever we want.

Chris Erwin:

Yeah.

Mike Gaston:

And so acknowledging that, realizing it, and then just pursuing things like that. That's one. And then the other one is saying yes to things. We're so interested in saying no, because it helps us optimize our world. But really it's just saying yes to things has created so much opportunity for me.

Chris Erwin:

Cool. Advice for media professionals going into 2021?

Mike Gaston:

Well one, no, the need state of your audience. I think that's a huge one. I think people ignore that all the time. All they think about are cool things they could do. But literally every media technology affords a new kind of participation from its audience and it transforms us in the process. Right? So print produces the reader. Then the bildungsroman then produces a reader who imagines their own life as an unfolding biography and the radio producer is the curator who deejays their life soundtrack. And cinema produces the captive audience, that television turns into the couch potato that the internet then optimizes in the binge-watcher. So what I would say to any media person is what kind of audience are you creating with the thing that you are trying to make happen?

Chris Erwin:

Got it. Lastly, how can people get in contact with you?

Mike Gaston:

On Instagram, hit me up at @antisocialtheory. On Twitter I am @beyoncefan206 and or just email me at [email protected].

Chris Erwin:

Awesome. Mike, what a great interview. Thank you for your time.

Mike Gaston:

Yeah, thank you, man. Appreciate it.

Chris Erwin:

Ever since I first met Mike, I've always believed that he was a very unique mind and that behind that was a very unique backstory. And on this interview, he totally delivered. I think Mike is a really special person. I learn a lot just from observing him and how his mind thinks. And it was a real delight having him on the show. 

All right. So real quick, a reminder that we have our upcoming live stream media and commerce conference, we're targeting March, but the dates are moving a little bit based on speaker avails. So it'll be a day of virtual programming and we're partnering up with a really great partner to make that day a bit more interactive than your typical Zoom webinar.

So we'll have panels that will talk about live sports, live stream e-commerce, panels from the creator and investor point of view and more. And then we're actually going to do a live demo showcase where there will be live live streams happening to the audience and where we also get a little bit of a behind the scenes on how they're going down. Should be a lot of fun and a great learning opportunity too. And then we'll do maybe just a couple of keynotes. RockWater will do a state of the industry and maybe one or two more. All right, that's it everybody. Thanks for listening.

Chris Erwin:

The Come Up is written and hosted by me, Chris Erwin, and is a production of RockWater Industries. Please rate and review this show on Apple podcasts and remember to subscribe wherever you listen to our show. And if you really dig us, feel free to forward The Come Up to a friend. You can sign up for our company newsletter at wearerockwater.com/newsletter. And you can follow us on Twitter @TCUpod. The Come Up is engineered by Daniel Tureck. Music is by Devon Bryant. Logo and branding is by Kevin Zazzali. And special thanks to Andrew Cohen and Sean Diep from the RockWater team.

Christian Baesler is the President of Complex Networks. Christian is a young media savant, who in his 20’s had more media experience than most executives have in a lifetime. We discuss his humble German childhood, how he launched Bauer Media's digital business at just 21 years old, being a touring DJ, and Complex's international growth plans for 2021.  

Subscribe to our newsletter. We explore the intersection of media, technology, and commerce: sign-up link

Learn more about our market research and executive advisory: RockWater website

Follow The Come Up on Twitter: @TCUpod

Email us: [email protected]

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EPISODE TRANSCRIPT:

Chris Erwin:

Hi, I'm Chris Erwin. Welcome to The Come Up, a podcast that interviews, entrepreneurs and leaders.

Christian Baesler:

I was there first as the student, still at my program. And I basically took the initiative to say, "Well, you say there is no opportunity here, why don't I just build a case study for you?" And so I programmed a website, plugged in the programmatic ads. And at first, I was also creating some of the content myself. There was, like, celebrity news on In Touch's websites.

Chris Erwin:

This week's episode features Christian Baesler, the president of Complex Networks. Christian is a young media savant who in his 20s had more media experience than most executives have in a lifetime. And he's a “get your hands dirty”-type builder. Like when he was tapped to be the head of digital at Bauer Media, right out of college and programmed the company's first website himself. And today Christian runs day to day operations of one of the world's largest digital companies, which includes hot sauces, a sneaker marketplace, live and virtual events, and so much more. And oh yeah, he even finds time to be a performing DJ throughout Europe. So yes, Christian is a rockstar, but as you'll quickly learn is also extremely humble. I'm pumped to tell you his story. All right, let's get into it. 

So Christian, let's jump back a few years. Let's start with where you grew up in Germany.

Christian Baesler:

Yeah. Where I grew up in Germany is, even for Germany I would say, not as popular place or as well regarded place, at least back then when I grew up there, it was heart of the GDR, the German democratic Republic or Eastern Germany, that only merged with Western Germany in 1990. And fun fact, I was actually born on the day that the German Wall fell. So November 9, '89. So my mother's always joking that's that one might have caused the other, I don't know which one caused what, but.

Chris Erwin:

Yeah, the whole like causality correlation thing.

Christian Baesler:

Probably the Wall falling was the cause for her giving birth that day. But I grew up in that area, that in terms of the economic environment had been very depressed. And for the next 10, 20 years after was integrating into Western Germany, but still there weren't that many of the same opportunities like there was in Western Germany. And in addition to that, I grew up most of the time of my childhood in small villages of like a few 100 people. I think the biggest place I lived in was like 1,000 people and everything was very rural. You had a lot of agriculture around and you would have to go 15, 20 minutes to the next nearest town at least, or to see other friends living out of town. So it felt very small and it wasn't the most progressive place, especially with the businesses that were there.

Chris Erwin:

And growing up, what was your household like? What did your parents do? Were they in a similar field that you are in now or totally different?

Christian Baesler:

Again, they grew up both in the GDR where it was mostly working class in general, in the GDR with the kind of jobs that people had especially living in villages. After the GDR became one Germany, my father, who was a plumber, started his own company doing plumbing. And so he was entrepreneurial, which previously in the GDR, you couldn't have your own business. There was no concept of privatizing where post he started his own local company. And so my mother was for the most part, a secretary in his company. Before that's in the GDR times, she was a waitress in restaurants. And I don't think I've said that in other podcasts or interviews before, my father passed away when I was 12 of cancer and so that was definitely a big moments of just unexpected big change and also something that was definitely a very difficult, but also important experience for me looking like now?

Chris Erwin:

Your memories of your father, is it that he was an entrepreneur and he ran his own plumbing business from what you recollect?

Christian Baesler:

Yes.

Chris Erwin:

Interesting. A lot of people think about entrepreneurship in the US or in the modern economy as go raise a bunch of money from Silicon Valley and have a big technology startup, but entrepreneurship takes many different forms; small businesses, blue collar businesses. Growing up in small communities of like a few 100 people, did that make you very curious of, "Hey, what else is out there? What else could I get into?" Or was there a level of comfort, which is, "This feels right. I could live like this with these type of people for the rest of my life." What was an early feeling, or if there's tension in your life?

Christian Baesler:

It was definitely, there must be more than this village life, which was comfortable and people knew each other around the village. So that was nice that sense of community, which I think is somewhat missing today in life in general, that it was more of a feeling of togetherness rather than everyone for themselves. So that was a plus, but I somewhat got lucky in terms of the time I was born on the exposure had early on in my childhood, because that was all pretty much at the development of the internet was just growing and computers were just growing, the personal computers were growing.

Christian Baesler:

That plus just overall TV getting bigger really gave me a window into what's out there in the world, which if you just live on the village and you read the local newspapers or some magazines, you have no idea what other lifestyles or what other cultures are outside of that bubble. And so I was quite early fascinated with computers in general, but then more importantly the internet, which was just a huge opportunity to learn about different things that otherwise I wouldn't have any exposure to. And that really showed me that there's more outside of this world I live in that I'd like to learn or immerse myself in.

Chris Erwin:

I understand that you began programming at a pretty early age, I think in your teens, early teens around 13. But your first exposure to the internet and computers, was it at home where your family purchased a computer for you or there was a shared computer or was it through local library or school? Because what I'm hearing from you is there were simple means growing up, like working class people in the community. So what was that first exposure to internet and technology?

Christian Baesler:

Yeah. My family as you mentioned, just in general by the nature of the environment and the jobs they had, they weren't wealthy by any means. So it was definitely not something that was readily available. We didn't have any computers at home, so that was not like an environment that I could benefit from, but I did have an uncle in my family that was very much into computers at the time. He assembled his own computers; buying all the parts and assembling all of them themselves. And so that was the first time I truly had an exposure to computers.

Christian Baesler:

And I was very fascinated by this concept of combining different things that if you plug them in, in the right way, it turns out to be this interactive device that then you can manipulate something on a screen with. That was very fascinating. And I would say the curiosity that I developed in this to begin with was probably within computer games. Just the idea that you can play on a device and again, influence what's happening on the screen was what sparked the initial interest and curiosity and computers then allowed me to create something myself that I can interact with manipulate like the games were previously.

Chris Erwin:

With the internet, what were you consuming? So games was a big part of that. And then did you start developing your own games as well?

Christian Baesler:

I started building games at the time, but what I was more fascinated with was programming languages around the internet itself. Early on, I think the first thing I started playing with, there was no big systems like Squarespace, back then you have to do a lot of the things manual yourself. And so early on, I remember being very interested in message boards, which was like this exchange platform for a lot of the communities and subcultures that might be on Reddit or other places today. But back then message boards were huge. And oftentimes message boards also got recorded by us for how to program. Like if you were stuck figuring out how to solve a specific programming problem, you could ask someone in the message board and this kind community would just take the time and help you.

Christian Baesler:

And so early on, for example, I discovered phpBB, I think it was called. It was like one of those WordPress like message board platforms that someone already built and you can create your own message board. But back then you had to host, you have to have your own hosting space and server and then you could style it. And so I took something that was existing like that and figure out how to do the hosting part and then started to manipulate it.

Christian Baesler:

And then over time it made me more and more curious to create websites on my own, which ultimately when I was probably 13, I started doing it. I made available as a service for companies and organizations in the local village at first, but then in the area. And so I developed websites for a fee for the local companies as probably the first big income source early on.

Chris Erwin:

When people think about the success formula, it's the power of curiosity and wonder coupled with serendipity and the right connections, and that you had this curiosity about you and then with your uncle who also had curiosity and access to the hardware and the software and interesting computers and intention to share that, what a powerful combination that puts you on a unique path.

Christian Baesler:

Absolutely.

Chris Erwin:

So then what is that transition where, okay, you're in high school, you're working these jobs and then I think there's a transition into interest in journalism before you go to university, tell me about like right before university some of the work that you were doing.

Christian Baesler:

Yeah. Some of the other work I did outside of the developing the website was I developed an interest in photography as well. And I bought myself, at least for that time, quite a good, I think it was called DLSR camera, which at the time was taking the best photos you could take. Maybe these days, all you need is an iPhone but back then, that's what you needed. So I was really interested in the idea of creating something in general, either websites or things for people to consume, which also could be images like photography and text. And so after playing around with the camera, I ended up also working for companies and for weddings as a photographer at first. And so some people trust-

Chris Erwin:

How old were you when you're doing wedding photography?

Christian Baesler:

Probably 15, 16, I would say. And so that made me interested in media, which is basically also creating something that people consume around photos and texts. And there was this local newspaper, which is basically one of those weekly things that you get delivered to your house often times for free and covered by ads, so they can monetize through advertising, but it was like the local newspaper and they had a freelance position at first to basically be a local reporter. I applied for it. And for whatever reason, I don't know why now looking back, my boss there eventually gave me a shot and trusted me to be this local reporter even though I was only 16 at the time.

Chris Erwin:

So the youngest reporter of the paper, probably?

Christian Baesler:

Probably, Yeah. I mean, I didn't see anyone else there in my age at the time and I wasn't paying too much attention to who the reporters are previous to me, but I would assume so. And basically with that job, I had to go around to different events and two different things happening in the region and interview people undocumented, both with texts, like articles that I wrote, but also with the photos because the budgets were so small, you basically had to do everything yourself as a local reporter.

Christian Baesler:

That was a hugely transformative experience for me because outside of just exposing them more to medium previously in my childhood and early teens, I was a very shy person. I wouldn't want to talk to people that I don't know. And it was very difficult for me to make conversations and this job required me. It was part of the job description to get information out of people. And ultimately this further, the desire to find out information with people.

Chris Erwin:

A theme that we'll get into later is this notion of subtle or soft power, which I believe that you embody. And so I was curious to where those roots are and hearing about your early age shyness, but clearly you wanted to express yourself, but maybe just differently relative to social norms. So that was the internet expressing yourself in gaming, and programming and building websites. And then as you said this desire to create and you're creating these stories and photography at the paper, a very interesting theme that takes you to where you are today, that we'll touch on a bit more. So you're creating and expressing in unique ways and then it's time to apply to college or university. And I believe that you ended up going to Nordakademie in Hamburg. When you went to university, what did you want to get out of it?

Christian Baesler:

Again, coming from a difficult economic environment where my family didn't have a lot of money even going to the government university wasn't as good of an option because they couldn't support me financially to like pay rent and to have the basic income to go through that school. And so there's one other interesting concepts which might be somewhat unique to Germany and it's called an integrated study where after high school, you apply at a company that is partnering with specific private universities and private for the reason that they basically create specific programs with these companies to give you a bachelor degree, you get a salary and you work half the time at the company. So it's a 10 weeks at the partner school, which in my case was Nordakademie. And then you had two to three months at the company where you're basically a trainee rotating them through different parts of the organization from marketing, to sales, to finance, they pay your tuition and pay your salary.

Christian Baesler:

And so that to me, as a concept integrated study in general was something that seemed like a solution. Like I could basically get an income and study at the same time. And so I was very focused on finding a place to get an integrated study. And originally I wasn't as singularly focused on media. I applied at Diamler, the car company. I applied at Lufthansa, actually the airline to become a pilot, which was something I was fascinated by early on. So it was different paths that could be going down.

Chris Erwin:

Wait, let me pause you right there. You said interest in being a pilot, had you flown, where did that interest come from?

Christian Baesler:

It was maybe another symbol of just going places and the freedom that had represented. And so I was always fascinated just by flying and pilots and airplanes in general. And again, growing up I played quite a lot of, I think it was Microsoft Flight Simulator, which I saw they just brought back as a new version the last month, but that was like one of my favorite games. And so I was fascinated by just the art of flying. And so I was seriously considering becoming an airline pilots at the time, applying at Lufthansa.

Chris Erwin:

It's Lufthansa and Daimler and you end up at Bauer in their integrated study program. And so how did it feel when you got Bauer? Were you excited?

Christian Baesler:

The Bauer one was one of the first that I got confirmation from. So the other ones weren't as quick in the process. And so it was the first option that was available, but then also in the moment thinking through what would it mean to go to the different companies that also felt like the most exciting, because it would allow me to do more of the things that I was already doing, meaning it was in the media industry, which again, as a local reporter had already worked in as a photographer and digital media was still nascent, but the concepts to build websites to then express the content on was something that they were very focused on at the time.

Christian Baesler:

So it felt like the best option based on my passion so far, but also they have like 100 magazines or so in Germany and some of them were my favorite from my childhood time. So I also had this excitement about now being at the company that makes the things that I consumed when I grew up.

Chris Erwin:

Got it. You were busy during your university years, you were at school and you were working a part-time job, but on a pretty serious rotation program. What else did you do in between then? We're going to get into your career trajectory very soon, which clearly you started early. What were other things that you were into?

Christian Baesler:

During that time, as you mentioned, it wasn't like a normal study where you have a three months summer break or few courses during the day and otherwise not much to do. So the three and a half years then was probably among the most intense time of my life. Maybe for the last few years career wise were more intense, but just up until then, it was the most intense time because it was classes from 9:00 until 6:00 and it was only a 10 week semester, which we had six big exams and there was no break, you had to then go to the company and work for three more months, different departments. And so there wasn't really that normal student life where you just travel the world or you just have this time to pursue other passion projects.

Christian Baesler:

But the one other passion project I developed quite early as well, going back to the idea of creating something is music, where I was really fascinated by how music is created and how if arrange sounds in a certain way, it could make people feel something just by nature of how it's arranged. And so pretty early on, I, again, thanks to the internet, found out what the tools are, which at the time already were software based. It wasn't that you had to have this big physical hardware environments. So I was quite early on playing around with different softwares for music creation and went deeper and deeper into that.

Chris Erwin:

And did you also perform as a DJ as well?

Christian Baesler:

Not in that time during my studies, but afterwards where I did both on the music production side, teach myself how to create my own music, but then I also learned how to be a DJ, which has different meanings. There's like the DJ that's basically just has a playlist of prearranged things like at weddings or other things. They have their purpose and that's definitely one component, but for me it was more the how do I create this experience that shows people music that they've never heard before and it sounds like a two hour long song or track rather than a clear difference actually three to five minutes? And so then I ended up performing multiple times in Germany, which I still did pre-COVID. So I'm still doing it now, if we wouldn't be in the current situation.

Chris Erwin:

Another unique form of expression. And I've never seen you perform and I know that your SoundCloud handle maybe as a current mystery, I wonder onstage when you perform, is it a more subdued presence and you let the music speak for itself or do you look at that? Is there a unique release there or maybe you enter a form that's unique to your professional leadership or character?

Christian Baesler:

It's definitely highly therapeutic I would say, because it's a different way of expression and also communication with the audience. And again, that the music I play is not like what you would hear in charts. It's for the most part electronic music, mostly techno music which for people that aren't familiar with, it might sound like jazz sounds. For people that don't understand or don't like jazz, it's just like this random sounds that are just being played. But for the audience that does appreciate it and know it, it's this very reflective experience.

Christian Baesler:

And for me, I get more instant gratification and joy out of doing this for 90 minutes and seeing the audience react to the music I'm making than doubling revenues or having some other usual measurement of success that feels more indirect. Like you see numbers in spreadsheets, but you don't really know what it means what's happening on the other side. And this is a much more direct feedback loop that is much more rewarding.

Chris Erwin:

And to be specific, your identity, your behavior on stage, would you say it's very different from your day-to-day life or is it similar?

Christian Baesler:

I would say it's similar. It's very reserved. With the techno music as a category, the DJ is in the backgrounds like the audience is not even meant to realize that there is a person there doing things, which is very different to when you go to festivals and they're all on big stages and have all these big lights. So that's kind of the opposite of what the electronic music culture or the underground electronic music culture would be about. So I'm basically the shaman in the background playing music for people to be in trance. That's kind of the goal of that experience.

Chris Erwin:

You're like that master of ceremonies pulling the puppet strings, little do they know that Christian or your DJ name is making that all happen? That's a cool thing.

Christian Baesler:

The best example would be just like it's a form of meditation where you can influence the behaviors of a big group of people just by playing certain sounds and everything happens in a synchronized way, which is incredibly fascinating that's possible with music as a human species, you can just align everyone through these quite simple ways.

Chris Erwin:

A unique form of leadership in a way. So let's transition now as you go from university and integrated study into full-time at Bauer. So I think this happens around 2008, there's some like various roles in the company. What's your transition into full-time? What does that look like?

Christian Baesler:

It was actually 2012 into full-time. So 2008, I started integrated study that went until 2012. And so that study started 2008. I was 18 turning 19. So right after high school, straight into this college integrated study program. And so when I finished in 2012, I was 22 turning 23. Normally you stay within that company for two years after. That's kind of part of the deal, which is great for the student because you have a guaranteed job. And it's great for the company because they get someone at an entry level rate, relatively speaking, that already knows the company for the last three years of having worked there. So it's a great mutual partnership. But usually you're supposed to stay in that location, which for me, was in Germany. I was in Hamburg, which is where the company is headquartered. And so there was kind of a role carved out for me in a certain team or division and everything is kind of pre-planned.

Christian Baesler:

As part of the integrated study, so during those first three, four years, there were two opportunities to go abroad. One was to study a semester abroad, which I ended up doing at Boston University. And then there was the opportunity to work abroad for one of those practical semesters. And I ended up going to the US office of Bauer Media, the company I was working with. And when I got there during the study part of the three, four years. First of all, I was very fascinated by the US studying at BU and the overall energy and culture and approach here seemed very different to everything I grew up.

Christian Baesler:

And so it felt very different in a positive way. And then working at the office in New York for Bauer right after, the energy in the office was also totally different. Everyone was much more focused, much more passionate to just do the best work. And more importantly, for my role there specifically, and again, I was still like a 20, 21 year old student at the time, the big opportunity I saw coming here was that there wasn't really a digital business yet that was already built out. There were print magazines and actually at the time, Bauer was the biggest magazine publisher selling at newsstands in the US. So like supermarket checkouts, at airports, all the usual places where you would buy a physical magazine. And so they were the biggest magazine publisher at the time with multiple magazines. The most well-known ones are probably In Touch Weekly, Life & Style Weekly, Woman's World and First for Women.

Christian Baesler:

And it wasn't like an oversight that they didn't have a digital strategy or the digital business yet, it was by the nature of their print business model. Traditionally, all the media companies in the US, the magazine media companies in the US are build on discounting subscriptions to lock you in for a period of time as an audience and then they monetize it through advertising. So it's basically getting scale in subscriptions, which often a loss leader to then make money through ads. So when all these other companies expanded to digital in the early 2000s, they followed the same model for the online business which is giving away content for free, which is basically giving away subscriptions or discounting subscriptions and then monetizing the reach through ads.

Christian Baesler:

And so Bauer made the majority of its revenues through actually selling a single magazine to the reader. They didn't discount any subscriptions. The ads was a small part of the business. And so that made them very profitable and very successful, but it didn't really lend itself to just be scaled online because people just weren't used to paying for that kind of content online.

Chris Erwin:

And a totally new muscle to flex in terms of trying to try a new business model, hire the right team against that new mandate, manage it. So enter Christian, right?

Christian Baesler:

Yeah. I got there, again, as a student at first in 2011, it was. And so again, that was kind of the context that were the successful print magazines that make most of their revenue through consumers. And there was no way to make revenue through consumers as easily online. And the usual business model is to get most audience possible and directly to a sales team, sell ads into it, which the company wasn't set up for to do both in terms of the people and the kind of focus that was there, but also it might've disrupted the print business more rapidly if we would have pursued a different approach online. And so the timing there, again, was very unique and very much in my favor, which are really like two things.

Christian Baesler:

One, there was not the emergence of more standardized technologies like WordPress for example, and other systems that were already pre-built were more readily available. You didn't have to completely invent everything from scratch. And the other big opportunity at the time that was developing was programmatic advertising, which means you don't need an expensive sales team to have human conversations with potential clients and convinced him that they should not spend this money with you which in our position at the time, we were one of the smallest in terms of online reach and probably not as differentiated to some of our competitors.

Christian Baesler:

So it was a lot of upfront risk to spend all this money on the team that might then sell something where with programmatic advertising, every page impression that we generates has a certain amount of ads on them. And they automatically monetize through Google or other partners without question. And so it became very predictable. If we have more traffic, we can make more money without having an upfront risk of hiring a team to sell that space.

Chris Erwin:

What I want to understand is when you come in, you rise to transform this company into digital and to lead an innovation of their business model. And you are tapped to do this at a pretty young age. So when you are tapped to lead this initiative, some interesting things happen. One, I believe that you probably to really diverged from your peers in a meaningful way that are the same age and two, you get your hands dirty and in the weeds more than I think, I've heard about a lot of other executives, you're building their digital websites and their tech stack yourself, not hiring another team yourself. So first talk about when you were tapped to lead this, what did that feel like? Were you excited? Were you scared? Was it like, "No, of course I'm going to do this." What was in your head?

Christian Baesler:

It sounded surreal at first. And just again, the context at the US company was what I described and so I was there first as a student still on my program and I basically took the initiative to say, "Well, you say there is no opportunity here, why don't I just build a case study for you?" And so I programmed a website, plugged in the programmatic ads. And at first, I was also creating some of the contents myself for the website to be published there.

Chris Erwin:

You were writing what type of content?

Christian Baesler:

There was celebrity news on In Touch's websites. After the first few ones, we ended up hiring some freelancers and relied on some additional support. But yes, in the beginning it was basically, let me show you that there's potential opportunity here while I was still a student there. And I was there for three months, and in that three months I could showcase that there's a probable business. We basically build the website and monetize it, and it was profitable just within that trial period of the time I was there as an assignment.

Christian Baesler:

At the end of that assignment, when I received the job offer to go back full-time to the US business and join at the time director of new media. And I was still like 21, 22-year-old student in university and I still had one more year to go, I still had to finish my school. And so that was hugely flattering and surprising to be getting that level of trust and also that kind of offer even before I graduated and it was actually frustrating and I still had to basically finish my school for another year before I could take that opportunity.

Christian Baesler:

So I did go back to Germany and finish the degree and ended up moving to the US in 2012 for this job. And at first I was very scared and concerned I would say, because there were two differences I would say that I was facing to anyone else coming into this role. One was just, I was highly inexperienced in a traditional sense because I never managed people before and I never had one singular boss before I rotated through the whole company but I wasn't part of a traditional team. So now, having to lead a department or in this case it was just me in the beginning but the agreement or the goal was to build it up. It felt very scary because I hadn't done it before and I didn't see it before.

Chris Erwin:

That's a lot of responsibility at a young age. You're already going through a lot of change when you graduate university, and now this is adding in... It's a lot of change that happens in your career in your 20s is now happening to you all at 21.

Christian Baesler:

Totally. And also in a different country. While I just had spent six months in the US to study semester here and to work for the company here, it was still now being in a different country with a different culture in a leadership position at relatively young age. And so that was definitely a period of me not feeling sure or confident if I'm ready for this, if I can accomplish the goals that are set or if I'm able to meet the expectations. But in terms of how I felt just about being given the opportunity, it was very, again, flattering.

Christian Baesler:

But also, just I was very positively surprised to receive that level of trust that someone took a chance on me so early on in my career, which I would say is a constant theme that goes back to people back then trusting me to build their websites, later to work for the local newspaper at a relatively early age. And so having people that trusted me, was probably the single most important way for me to progress with these opportunities.

Chris Erwin:

Well, and putting in the work to be rewarded with that trust. But also just again the serendipity, Bauer a traditional media business that could really be empowered by transforming to digital and with your background and skills it was like right place, right time.

Christian Baesler:

Also, it's right place, right time but also I think in general when I talk to other friends about it, it's making sure that you are available for opportunities. You put yourself out there and you put in the hard work, but then when they arise that you go for them. It was definitely a difficult decision for me to say, "Okay. I'm not going to move by myself to the US and take this role and go into this uncertainty." And actually at the time, Bauer in Germany was against me going to the US even though the US part of the company wanted to hire me because they said, "We're educating for the German market and we have this path set out for you here," which was a more traditional progression.

Christian Baesler:

It was like, "You're going to be this junior project manager on this thing over here." And so that was ultimately decided against, as in they didn't want me to go to the US. And so I basically advocated and lobbied and showed what the potential benefit is or the risks of me not going for a few months to ultimately convince them otherwise. If I would've given up at the time, I would probably not be here where I am today.

Chris Erwin:

As we like to say, you stood in your power. You had a point of view and you put your foot down and said, "There's a major opportunity in the US, it's where I want to be and I'm going to make this a mutual win." And I like how you said, availability for opportunities. When people talk about success, there's luck that comes into it but it's increasing the likelihood of luck. I'm reading a book called, The Psychology of Money by Morgan Housel. And he talks about setting up your life, your finances, your health, so that when that opportunity comes along you can pounce and you are in a situation where you very much could and could very much make the case. Look, there is a lot more that we could talk about with Bauer. I know we're probably going to rush through the next five to six years there but I want to make sure we have time to talk about Complex, because there's a lot there too.

Christian Baesler:

Of course.

Chris Erwin:

A big question that I have is, I look at your next years at Bauer; you're navigating profitability in unprofitable times and you look a lot of digital peers in the US. And I was part of this world, the MCNs and all the digital studios that emerge out of Google original channels program, a lot of companies that did not succeed. And then you end up running two businesses at once, a UK media business and a digital business. I'm curious, high level, how did your leadership evolve during that period of coming in as a newbie leader at 21, 22, to the type of leader you were at the end of this incredible experience? And we'll save another podcast again, to the details there.

Christian Baesler:

I would say it evolved from not being sure what it means to be a manager and how to lead people, let alone different culture. When I first started to having to figure out how to do a lot in the weeds with other people in the US part, to then hiring a more senior team that then I was working with on a much higher level being less in the weeds. So in the end of my US time, we actually separated out the digital business into its own company called Bauer Xcel Media with standalone content creation technology, everything you can imagine having in a traditional visual media company. And so we had C-level executives, we had vice presidents, senior presidents for different functions.

Christian Baesler:

And so I transitioned from being the person that creates the content or writes the website to managing senior people at all times really, were older than I was. And so figuring out how to motivate and mentor people in their day-to-day work with me having had less work experience, was definitely one challenge. And it was the startup nature I would say in the US, when I ended up going to the UK as well. Where Bauer is the largest magazine company and Europe's largest radio company, it was kind of the opposite situation. There were already hundreds of brands and hundreds of people across all those brands that worked on digital, and I joined to oversee the digital business. And so I inherited an existing business with existing practices and that was mostly I would say big learning on change management, how do I build partnerships throughout the organization of other functions that don't report into me? How do I get alignments as I think about restructuring and making large scale changes of how we work and who was in certain roles?

Chris Erwin:

This is interesting. So let me ask you specifically, mentoring people and hiring people that are older than you in senior roles that you're the ultimate leader, what worked well for you to be able to do that?

Christian Baesler:

There were two parts, there's making sure I convinced people to join the company I was with from other jobs that were companies maybe they were more established to what we're trying to build. And so at that part, I was worried about what was the vision and can I show enough confidence and enough support to make them feel like they can truly build something here. So that was really the big opportunity to co-create or co-build something, but then in turns out actually working with them is finding the right people and then letting them do their work without interfere. So I was seeing myself more as a mediator or almost like the role of a therapist, of making sure they have the tools to work towards achieving their goals without me necessarily telling them what to do in there functions.

Chris Erwin:

I like that a lot. One of the greatest lessons that I learned was from the old founder and CEO of Big Frame, Steve Raymond, who said, "Hire great people and get out of the way and empower them." Beautiful, simple words and it works.

Christian Baesler:

Absolutely. And I think that's also what makes people feel like they're trusted and they have the freedom to truly make an impact.

Chris Erwin:

So Christian, we just took a break. We were talking about change management at Bauer and one of your proudest moments, why don't you tell us about that moment there?

Christian Baesler:

So looking back throughout my career the proudest moment I had is, at first in the US we were able to separate the digital business that I was tasked with creating into its own division, into its own company. The overall company is called Bauer Media Group, it's one of the largest media companies in the world, a couple of billion in revenue and more than 10,000 staff and one in a thousand radio, TV and magazine brands. It actually might be the biggest magazine company globally in terms of circulation. And so it's a huge organization.

Christian Baesler:

And so in the US when I was busy, at first the only person doing a digital business in the end we were roughly 50 to 60 people just for the US digital business and spun it off into its own company. The inspiration for me for that was the innovator's dilemma book which is basically, why do big companies that are successful in one industry fail when they're not seeing kind of the innovations around the corner and where things are going? And I thought that in general with print media and specifically at Bauer that was on the horizon and really the only way to solve for it is to create a separate company that in the context of the new market is big relatively speaking, because at Bauer the problem was always printed, so profitable and it's so big, why do we care so much about the small digital dollars? We don't want to cannibalize ourselves.

Christian Baesler:

And realizing that it's inevitable that digital would be bigger than prints and if we don't cannibalize ourselves our competitors will cannibalize us. And so ultimately, I got them to spin off in a separate company in the US at first called Bauer Xcel Media, which I then became the president of. And because we have been profitable every year since the beginning and scaled other 50 people and we're still highly profitable, which as you mentioned at this time was unusual with a lot of venture-backed companies raising hundreds of millions. I ultimately convinced the ownership, it's a family owned company in the fourth generation, to roll out that model globally.

Chris Erwin:

How did you convince them? Was it you just call up the family owner, the patriarch, and say, "I want to do some change?" Was it scheduled big board meeting? What was that process?

Christian Baesler:

I only really learned about what board meetings are after joining Complex now, because back then in a family owned business the board is the owner and so in this case is one person that owns more than 90% of the company. And so we would have monthly or quarterly check-ins with her and some of the other management team she has, just talking about business progress. And at the time they were super fascinated that we were able to build such a profitable business with no investment upfront and relatively little resources. And so they were really curious how we did it and why we were succeeding. And the business grew even more and was even more profitable after we spun off to be a separate business. Ultimately, it led to a conversation of, why are we not doing this in every country?

Chris Erwin:

When you have management saying, "Why are we not doing more of this?" That's a great place for you to be.

Christian Baesler:

Exactly. And ultimately, they rolled out Bauer Xcel Media as a concept of separating the digital business from the traditional magazine or radio business in every other major markets. And ultimately, the goal was to have one global platform. So one content management system, one ad tech stack, all the things you would imagine having locally and that's what enabled me then to also take on the UK business operationally to basically do the same business expansion there.

Chris Erwin:

Last question on Bauer, Christian, did you say that you came up with the name Xcel Media, the digital unit?

Christian Baesler:

Yes.

Chris Erwin:

What was the inspiration for that? And was that a proud moment to say, "This is my name, my stamp on the company."

Christian Baesler:

It was definitely the proudest moment and I think they still even use it now, every company and every country now that does digital is still called Bauer Xcel Media. So it's kind of my legacy now within the company that they're still adopting my name and the logo we created and everything. The name, it's difficult to find a good name in general and it doesn't always have to be super prescriptive of what it is that you're making, best example the Apple that sells computers. The name I think is completely arbitrary just to make sure it's not something negative.

Christian Baesler:

Traditionally, any kind of digital team within the company was called 'New Media,' which was my title actually. Director of New Media, which what does that mean in the context of everything or 'Digital Media,' which eventually everything will be digital at some point. And so we wanted to find something that wasn't so limiting in what it could mean or it would be out of date a few years later. And Excel just as a name, like the spreadsheet software, just thinking of doing something better and that's more progressive than what we've done so far was the inspiration. I think we just decided to leave out the E like the software, it's spelled X-C-E-L just to make it sound a bit more fancy. But that was the goal to find something lasting that sounds more inspiring.

Chris Erwin:

Yet another creative fingerprint from Christian that touches audiences, people in society in a unique way. All right. So speaking of interesting names, we now transition to the Complex part of the story. So you're at Bauer for about 10 years, a decade, maybe you're on the path to be the CEO, but something causes you to rethink where you want to be. And I'm curious, were you seeking out change or did change come to you or a mix of both?

Christian Baesler:

Actually, the change I was seeking at the time after 10 years at Bauer was a break and time to reflect. My plan was to take at least a year off and do a world trip in a way that I think was only possible at that time and maybe still now, meaning I didn't want to plan anything upfront. If I wanted to stay a certain place I like it, I might stay longer or not. Where I feel like you can take a vacation or even a sabbatical you're still at work, you're still thinking about work, you're still checking emails.

Christian Baesler:

And so I truly wanted to be completely disconnected from everything and if I hate it, then I can stop after two months and if not I would go longer and so that was my goal. And after 10 years in Bauer and the end of it living between London and New York, which was fun but also very tiring as we would fly every week or every two weeks between the two cities; I slept like four hours a night, I felt like I needed a break. So I resigned actually my roles at Bauer for that reason. So I wasn't actually planning to work again right after this.

Chris Erwin:

How much time was there? Did you get a reprieve? Did you get a vacation? What was the gap before you went to Complex?

Christian Baesler:

Probably a month I would say.

Chris Erwin:

A month, okay.

Christian Baesler:

Not what I had hoped for.

Chris Erwin:

I was thinking about this notion of sabbatical or time off recently. And I think it is one of the healthiest things that you can do, but I also feel that young up and comers feel well, "I'm going to get out of my groove. I got relationships, people like my work," and they don't want to change that. But I actually think spaces' transformative. So what was the special moment? Was it a conversation with Rich that made you change this whole big plan that you had been formulating for a while?

Christian Baesler:

Exactly. So Rich and I reached the founder and CEO of Complex, we've known each other since I think 2014. We met at a Digiday conference that we were both speaking at and we stayed in touch, maybe every three months or so we would have breakfast or lunch just to talk about what's happening in industry and what we're seeing in our businesses. I've always enjoyed my conversations with Rich. I was always very impressed by what Complex was doing and how fast it was growing.

Christian Baesler:

And so I would just meet him on ongoing basis, including when I just had resigned my role at Bauer and basically mentioned to him that I left or I'm actually leaving. After a six months’ notice, I had to serve out which is a very European thing that even after you give notice you still have to work for at least three if not six more months, but I already had resigned but I was still there for six months. And I told him I planned to do a world trip and from that moment on he basically pitched me into join Complex instead. And so the one month was basically the compromise to still have some time off in between.

Chris Erwin:

So it's Rich's fault, he blew up this once in a lifetime chance for an amazing vacay. What did he tell you or show you that caused you to just totally change your thinking and come on board?

Christian Baesler:

Two things, the ability to focus on fewer brands and go deeper. At Bauer in the US we had 15 brands, in the UK when I was still in UK business it was more than 100 brands. So you never really focused on a brand in the role that I had there, it was always systems and processes and people and so it was very abstract, where this was truly a brand business.

Christian Baesler:

And then the second part which was the most exciting for me as well, it's just the diversity of the business in terms of the business models. Everything I had done previously was traditional digital media of building websites and optimizing the monetization of those websites for the most part, where at Complex it was also a huge TV, video business, a huge events business, a huge actual commerce business not just affiliate. So I also felt like I would learn a lot and get a lot of experience in areas of media and entertainment that I hadn't had exposure to previously.

Chris Erwin:

So Rich recruits you, what is your mandate on day one? "All right Christian, you like our vision, here's what we need you to do." What was that?

Christian Baesler:

I would say my main mandate was to optimize the operations of the company, that the company had been through a lot of growth previously and was acquired in 2016 by Verizon and by Hearst. And so I joined two years later. And so now it reached this point of maturity as an organization in terms of much bigger staff now and many more goals and so my role was created to help create focus and reorganize what we do and how we do it, but also to continue to scale it to the next stage of growth.

Chris Erwin:

I'm thinking back to your 21-year-old moment being tapped as the director of a department at Bauer. You were scared then. You were excited about the responsibility but natural anxiety. Now you're entering an exciting, well-lauded company in digital media and entertainment at a very senior level. What were your feelings at that point?

Christian Baesler:

I think at the beginning it was also a question of to some degree anxiety, because there were two unknowns or two uncertainties. One, at Bauer I was there for 10 years and even if I switched between countries or switched between roles I already had established myself, people internally knew me and I already had trust of the people around me. When I went to the UK, people already knew I did something successful in the US office so there was an established relationship or awareness, where here I felt like I was the new person coming in and I had to prove myself all over again.

Christian Baesler:

So that was definitely a big unknown or a big source of anxiety in the beginning of, can I do it again? Can I prove myself again? And then the second part was just around as I mentioned it, I was very excited about the opportunity because of the expansion to other areas of media entertainment that I hadn't done previously but now it was also my job to work in those areas not having had done them previously in such a way. And so there was also the question of, how quickly can I get up to speed to make sure we're doing better as a business as a whole, including those areas.

Chris Erwin:

How did you prove yourself? How did you gain trust with this new team right off the bat? What was your immediate approach?

Christian Baesler:

And with that it was very helpful to just have been at the UK part of Bauer which was established team, established company, everything was already there and I was brought on to optimize it in the UK. It was an incredible learning experience in my most recent role prior to apply here. And so the big learning was, to build trust first and to truly understand what's working and not working is to take the time.

Christian Baesler:

So the first three months of joining, I would not make any changes. I would not introduce anything new unless it was obvious or easy just so there's time to build relationships and to basically go on the listening tour and hear from everyone throughout the company what's working, what's not working and through basically creating a list of opportunities and issues I would get buy-in from each of the established people throughout the company to then collaborate on solving all the various issues or optimizing all the various opportunities.

Chris Erwin:

I love that. You're a big new executive, people might expect you're going to come in and mandate all this big change, new culture, the best leaders don't do that. There's an existing culture. There's a lot of smart, great people, listen to them, process that and then you start to add your flair to the business over time. So you joined Complex, this is back in 2018, this is two to three years ago?

Christian Baesler:

Right.

Chris Erwin:

Now, you know our team and I write about and I tweet about, why I think Complex is so special, that you guys have built this very impressive, diverse business across media, ads sales, commerce, E-learning events, virtual events, the gamut and which I'll let you talk about. I want to hear, why do you think Complex is so special? Talk about the business of what it is and why it is so unique to its peers and just in the overall media market place.

Christian Baesler:

I think the three reasons or answers why we are so successful or why we are different to some of our peers, the first one is just; which is the biggest one is, passion for the things that we're covering and creating. We don't cover certain contents or create certain content because it's popular in Google or Facebook right now and we think there's a revenue opportunity, if we were to cover it. All the things that we're creating which historically was mostly in the hip hop and sneakers and streetwear space, we've been pants off from the beginning when they were all still niches and subcultures early in 2001, 2002 when the company was started. And so it's that deep passion that leads to authenticity, like are people actually care about what we're creating which then resonates differently with the audience.

Christian Baesler:

And so we have benefited as a company from those content categories now being as big as they are with hip hop being the biggest music category and sneakers and streetwear is the biggest in fashion. And we expanded to other verticals since then, but it's really finding people that are truly passionate about the content that you're creating. From a business model perspective, I would say the second big difference is that we think about everything in a 360 connected way. We don't create a product that's a website and then separately we think, "There might be some revenue in events, let's create a completely different event just so we have an event." Everything is connected.

Christian Baesler:

And so one good comparison I could give is Marc Ecko, who's the co-founder of Complex together with Rich who was also a fashion designer, he compared it to us not trying to be like another print magazine at the time like The Source or XXL [inaudible 00:50:27] or from a TV perspective not like MTV but a youth cultured Disney. Disney, meaning like they think about each of their shows and movies as IP that then translates to all these different revenue streams across events and commerce rather than afterthought and that's really how we're approaching a lot of our businesses.

Christian Baesler:

And then the third one which I would say is helping us especially in these times today and I was very impressed by as well when I was talking to Rich before joining, it's just the responsibility from a financial perspective that the business has had and has been taken for for years now. We, as the company now, didn't raise a crazy amount of money like some of our peers did, which made us much more focused on running a sustainable business from the beginning. And so with that, we've been running a business that's been profitable for years now which allowed us to be much more dynamic and much more flexible in how we make decisions.

Chris Erwin:

I think to that last point because you probably won't say it yourself Christian due to your humility, but from personal experience in digital media and modern media there is a lot of founders that are great visionaries, have an idea of where they want to build to but don't know how to build sustainably towards that end. And you exhibited in your career from early days of wanting to build and create, having the lean resources that you had access to, it's like you had your uncle's computer hardware do what you can with that. Then going into Bauer and learning how to do that at a company, I feel like this was ingrained to you not only very early on in your childhood but also in your early career.

Chris Erwin:

And I think that you are a special leader that a lot of other companies lack that don't bring this discipline nor this focus. And it speaks to another sentiment which is at a lot of media companies studios, is usually a complimentary leadership, like a great business mind and a great visionary. And I think that you and Rich can serve as both, but you're optimizing the day-to-day being in the weeds with the team and also having incredible passion yourself for these brands and where you want this business to go. It feels like a very exciting setup for where Complex can go next. But I don't like to overly editorialize in these interviews, but I do want to call that out for the listeners because I think it's special and worth hearing.

Christian Baesler:

Totally. Thank you so much. I very much appreciate the kind words.

Chris Erwin:

Of course.

Christian Baesler:

I think the overall theme is definitely resourcefulness of just trying to figure out how to make things from very little, where in my case growing up that was just the environment I came from as I mentioned. But also as a company, I think if you have too much funding available it leads you down wrong decisions more easily and you don't realize that you made wrong decisions until you run out of money, so that's a very dangerous path. I do think there is still value in raising money if you have highly scalable business models, let's say if you have subscriptions with a proven cost per acquisition and other things. But for where media is today, it's not as beneficial as people thought it would be five or 10 years ago.

Chris Erwin:

So with all of those nice things being said, let's talk about something that you and I have chatted in coffee shops before and with Rich, that you feel a lack of industry recognition by your peers, by the press, Complex doesn't get the attention or the notoriety that it deserves. Why don't you expand on that a little bit.

Christian Baesler:

In general, there's still I would say in the traditional B2B world but also just in a general consumer perspective of people that might not be of our audience and non awareness of either who we are in general or how big we are and how diversified we are, all the things we're doing as a business. But just I think the most simple fact would just be that we, based on Comscore which is the standard measurement for digital media in the US, reached to most 18 to 34 year old males in the US more than any other media company and more than double to Vice and still most people know Vice or think of Vice as the biggest youth culture brand.

Christian Baesler:

And I give them a lot of credit for having done great marketing and they raised a lot of money for being able to do so over the years. But there's also another prejudice which is, the things that we do and the things that we cover like sneakers or hip hop both as a music as well as culture are niche. Meaning there are small, passion groups of small audiences. But actually, hip hop by far now is the biggest music category in the US and sneakers are a huge growing business, that's the fastest and biggest in fashion now.

Christian Baesler:

And so those industries are now mass and today's youth, meaning 13 to 40 probably, are incredibly passionate about them. So we're dealing with kind of a prejudice or to some degree ignorance about the markets with those things being perceived as niche, as well as our role in that overall market that we've been working through for the last few years of changing that awareness holistically.

Chris Erwin:

That sense about the prejudice of being niche focused and I think you've also talked about even the stigma around streetwear culture and hip hop can impact you. I never thought about that before, but it's interesting to think about. All right. So at Complex, you guys have a lot of different brands, a lot of different businesses. Let's talk about some of your favorite children, which I don't know if you often do but we've learned your passions in this interview. What do you kind of love the most working on there, some of the content that you have?

Christian Baesler:

I think the most obvious one to mention now that maybe most of the listeners know as well is Hot Ones; our interview show where celebrities eat chicken wings while they get interviewed and those chicken wings gets spicier and spicier. And so it's highly entertaining to watch but also to work with the team on and it's been an amazing experience to help them diversify their business beyond advertising into hot sauce, into a game show, into a board game. So that has been an incredible experience.

Christian Baesler:

But then we also have shows like sneaker shopping, where we have a host go into sneaker stores, interview celebrities in context of sneakers that we diversified into education programs, basically learning how to get into the sneaker industry as a student. But also, up and coming shows like Full Size Run which is a weekly show where we interview celebrities, talk to celebrities as a talk show talking about the sneakers of the week that were released. That's kind of the show that's on the next level coming up.

Chris Erwin:

And what's the name of that again, Christian?

Christian Baesler:

Full Size Run.

Chris Erwin:

Full Size Run. Got it.

Christian Baesler:

And so that's on the more entertainment side, we also have programming that's more investigative, more serious news journalism with our biggest show there called Complex World which looks at different issues throughout the country, especially in the upcoming election cycle. So it's a balance between the entertainment part of it that's more fun and more casual, to the more serious journalism as well.

Chris Erwin:

And what you talked about, which I want to make clear for the listeners is you talked about E-learning classes for how to launch streetwear products and businesses. And I think a very cool new theme that Complex has spearheaded in our industry is, we're not just hip hop, streetwear culture and news and reporting, we are expertise in understanding of this space. And that allows you to expand your business in many different ways and to sell that expertise to other businesses, advertiser clients or even youth who are in undergrad programs at Parsons or FIT for example, and to make them better entrepreneurs in your verticals, that is just an awesome thing.

Christian Baesler:

Absolutely.

Chris Erwin:

All that being said Christian, you love DJing music. So is it Pigeons and Planes? What's one of the brands that you do a lot but what for you that really resonates with your heart?

Christian Baesler:

I think Pigeons and Planes resonates because of my passion with music because the focus of Pigeons and Planes is to give emerging artists a platform before they are big enough to be covered by the more traditional music publications or even by Complex and that to me is the most important part of the ecosystem. Everyone that has great talent has the same struggle in the beginning which is, how do I get awareness for what I'm doing? And having a brand within our portfolio does just that, not just through social media and articles, but we do events where we bring emerging artists onto the stage in different cities, has been a big passion of mine for sure to work with.

Chris Erwin:

All right. So a couple more questions on Complex and then we're going to get into the rapid fire and we'll close this out, how's that sound good?

Christian Baesler:

It sounds good.

Chris Erwin:

I don't think I've fully exhausted Christian yet, but maybe getting close in this marathon. Where do you want complex to be in 2021 that you're not right now?

Christian Baesler:

The main goal that we still have ahead of us that got somehow paused this year is internationalization or globalization. Right now, we are the biggest youth culture company or collection of brands in the US. And what's quite unique right now is that the passion points and the topics that we are the experts on here, are also the biggest in many other markets internationally. So again, hip hop music as a culture and sneakers and streetwear, but there isn't a brand like us or a company like us that services that in the same way. And so that's something we've been looking at all of last year and this year as well, that we'll be focusing on next year.

Chris Erwin:

And does that expansion strategy include local partnerships or raising more capital and actually building out local infrastructure, a mix thereof, what are you thinking?

Christian Baesler:

The model that we've applied so far and we already have a great partner in Canada with Corus, one of the biggest TV companies there, is to find local partners that already have the infrastructure from content creation to sales, to potentially the events production capabilities to execute the 360 nature of our partnership rather than us trying to reinvent the wheel upfront. So we've been in various conversations in multiple countries to replicate that kind of model.

Chris Erwin:

And I know that ComplexLand is coming up in December. Tell our listeners a little bit about ComplexLand.

Christian Baesler:

ComplexLand maybe just as a quick context, we usually do an event once a year called ComplexCon where you have 60,000 people in usually Long Beach, California. Last year, we were also in Chicago for the first time. That's been two days inside of the convention center with 200 brands buying products, roughly $20 to $30 million worth of products they're buying in that weekend after already paying ticket fee to get in. And then there's also a music stage and a food festival and talk stage similar to Ted Talks. So it's like this 360 modern festival with a high degree of shopping. So this year, obviously that got canceled due to COVID.

Christian Baesler:

And in general irrespective of ComplexCon, we've always been wondering what would a digital expression look like of everything we do every day at Complex Networks throughout all of our brands. And we were very inspired by things like Fortnite and Travis Scott collaborating to create this music experience inside the game and some of the other trends that are happening with Animal Crossing and Roblox where you have much more of a social community inside a virtual world.

Christian Baesler:

And so we've been working on this virtual world, virtual experience where you are an avatar like in a game that you can walk around in and it's called ComplexLands where we are recreating our ideal worlds with different zones that integrates brands of advertisers as well as brands you can buy retail products from but also music performances. So it's our expression of what all of our content and brands would look like in a game like experience.

Chris Erwin:

Will your DJ identity be making an appearance at ComplexLand?

Christian Baesler:

I don't think so. I don't think that's a going to be merged, maybe next time.

Chris Erwin:

One last reflection point before we move on to rapid fire. Christian, looking back on your career, I think you've won by choosing well and leading well. Again, putting yourself in the space for opportunity and being able to take the plunge when ready. And what you haven't talked enough about that I just want to highlight again is, your ability as a leader to be a change maker for the companies that you join and it's why you've been able to succeed. I don't know if you want to call your age out on here, but I think you're like 30, 31. You're a very young man. I think this podcast will probably air around your birthday, but your leadership has changed your company, the people that you've led, the past companies you've been with. And dare I say, I think you're also inspiring a lot of our industry peers as well. So I give you a kudos and a thank you, you particular. And to Rich and the Complex team, keep on doing what you guys are doing it's absolutely awesome.

Christian Baesler:

Thank you so much. That's very kind to here. Thank you.

Chris Erwin:

All right. So rapid fire. So these are meant to be short responses, either a couple of words, a couple sentences is okay. So we'll fly through them. Do you understand the rules?

Christian Baesler:

Yes.

Chris Erwin:

Okay, great. Proudest life moment.

Christian Baesler:

Proudest life moment for me was starting Bauer Xcel Media at the US first as a separate entity and seeing that scaled globally in all the countries that Bauer's in, which were 20 or so.

Chris Erwin:

What do you want to do less of in 2021?

Christian Baesler:

Definitely less screen time. It's always concerning to see a report at the end of every week on my phone about how many hours per day per week I spend on my devices and more of would be personal time, of spending time with people in person once that's possible again, post pandemic.

Chris Erwin:

Advice for media professionals going into 2021?

Christian Baesler:

I think the main constant will always be in our industry, regardless of what happens that everything will change. So continuing to stay nimble and to continually iterate, I think are the most important things both in 2021 and beyond. Nothing stays as it is or at certain, even if things are getting better.

Chris Erwin:

In future looking, what are one to two things that you think will drive your future individual success?

Christian Baesler:

I think the parts that I still need to work on more, both in the professional life as well as on a personal basis is, I'm very matter of fact when I communicate with anyone especially at work and everything is very I wouldn't say task-based, I'm more on the operational side in terms of my mindset, I don't know if it is the right or left brain, but definitely more the logical side. Just more emotional intelligence of how to work with people to truly motivate or relate to work more with empathy than I think I did previously. That's definitely an area where I have the goal for myself to do better or open up more.

Chris Erwin:

How can people get in contact with you?

Christian Baesler:

Twitter would be cbaesler with B-A-E-S-L-E-R and then LinkedIn is probably the most direct way to make sure we stay in touch.

Chris Erwin:

Christian, that wraps our interview. Thank you so much for your time.

Christian Baesler:

Thank you for having me. It was amazing for being on here. Thank you.

Chris Erwin:

I look forward to part two. Wow. Like I said in the beginning, Christian's list of accomplishment is super impressive. As you guys can tell, he's very humble, comes from very humble beginnings and is very understated, I think these are very unique characteristics for him as a leader. And I think that he's just very much in beginning of his career. I'll have to catch up with him after ComplexLand, the virtual event that his company is hosting I think December 7th to 11th. That's going to be a really interesting benchmark for the industry and I want to hear how it went afterwards.

Chris Erwin:

All right. Quick update on RockWater is that, again we have our livestream media and commerce conference that's coming up March 3rd of 2021. I think we're going to call it a mini con, maybe like LMAC for short. And we'll probably have a keynote from RockWater and then a couple of fireside chats and maybe two or three panels, we have a great list of executives that we're already talking to. If you want to get involved, shoot us a note. You can reach out to us at [email protected]. But it'll be super fun. All right. That's it. Thanks everybody for listening.

Chris Erwin:

The Come Up is written and hosted by me, Chris Erwin, and is a production of RockWater Industries. Please rate and review this show on Apple Podcast. And remember to subscribe, wherever you listen to our show. And if you really dig us, feel free to forward The Come Up to a friend. You can sign up for our company newsletter at wearerockwater.com/newsletter. And you can follow us on Twitter @TCUpod. The Come Up is engineered by Daniel Tureck. Music is by Devon Bryant. Logo and branding is by Kevin Zazzali. And special thanks to Andrew Cohen and Sean Diep from the RockWater team.

Chas Lacaillade is the founder and CEO of Bottle Rocket Management. Chas took a big bet on the digital video revolution, and now builds businesses for some of the most exciting creative talent from New Hollywood. We discuss why he left a prestigious talent agency to sell water pumps, Louisiana roadtrips, and how he converted a $5,000 bank loan into a multi-million dollar business. Full episode transcript is below.  

Subscribe to our newsletter. We explore the intersection of media, technology, and commerce: sign-up link

Learn more about our market research and executive advisory: RockWater website

Follow The Come Up on Twitter: @TCUpod

Email us: [email protected]

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EPISODE TRANSCRIPT

Chris Erwin:

Hi, I'm Chris Erwin. Welcome to The Come Up, a podcast that interviews entrepreneurs and leaders.

Chas Lacaillade:

I had my Jerry Maguire moment where I called all my clients and said, "Am I your manager? Am I your manager? And if so, this is my new endeavor, I'm going out on my own." It was terrifying. I took out a $5,000 loan from Chase Bank to live, and there was no interest for the first 18 months.

Chris Erwin:

This week's episode features Chas Lacaillade. Chas took a big bet on the digital video revolution, and now he builds businesses for some of the most exciting creative talent from New Hollywood. Yet Chas's career has a lot of twists and turns, and includes a lot of early disillusionment to be honest, like when he left a prestigious Hollywood talent agency to sell water pumps. But Chas's ambition eventually pays off. A Louisiana road-trip inspires a new career and soon after he turns a $5,000 bank loan into a multi-million dollar business. So Chas is a close friend of mine, and he's known for telling you like it is. It makes for fun listening. All right, let's get into it.

Chris Erwin:

Quick heads up, that my interview with Chas was recorded back in December and prior to COVID. Chas, welcome to the podcast.

Chas Lacaillade:

Great being here.

Chris Erwin:

Before we go through your entire entertainment story which is an impressive one, let's talk about some of your early days. Where did you grow up?

Chas Lacaillade:

I grew up in Lincoln Park, a neighborhood in Chicago which is very picturesque, very walkable. I attended schools in the neighborhood. All my friends lived in the neighborhood and it was great. I just had a really magical childhood, to be honest. I walked through Lincoln Park to my school, on winter days I'd walk through this enchanting, snow-covered park back home from school, and I'd have lots of time to review what I'd experienced that day, and what was going on in my life, and what I wanted to do. And I think that meditative time was really helpful for me in getting in tune with my thoughts because your teenage years are so frantic, and there's so much insecurity. You know, it took me about 40 minutes to get home probably, or between 30 and 40 minutes to walk home from school, and so-

Chris Erwin:

"Up hill both ways-"

Chas Lacaillade:

Yeah.

Chris Erwin:

... as my father used to say. He was also from Chicago-

Chas Lacaillade:

Yeah.

Chris Erwin:

... which was considered a pretty flat neighborhood overall.

Chas Lacaillade:

Yeah, and dodging crossfire from enemy combatants. And so, just walking home gave me some contemplative time, it was very therapeutic, that probably a lot of kids don't get.

Chris Erwin:

So in these meditative moments, were you thinking about your future career and that you were planning to start something, or was it more of like the whimsical child fantasies and fun back in the day?

Chas Lacaillade:

Well, I was a big reader as a child, so I read a lot of fiction and nonfiction, and I consumed a lot of biographies from basically, the age I could start reading. And biographies on a really wide range of people. So I remember when I was 12, reading Muhammad Ali's biography, and then Ayatollah Khomeini's biography.

Chris Erwin:

Wow.

Chas Lacaillade:

Just a real span of people because I was interested in a lot of different points of view, and the more I became exposed to what was out there and the different ways to obtain leadership, and fame, and infamy, and repute, and accomplishment, the more I became fascinated with what was possible if you just created a path for yourself.

Chris Erwin:

Yeah.

Chas Lacaillade:

And so, a lot of my thoughts were dedicated just to reviewing what these people who really impressed me, how they got to where they did. And how I could chart a path for myself that would employ my personal interests, that could hopefully some day lead to me being successful and known.

Chris Erwin:

Through many of our conversations over the years, there's a strong sense that you are highly ambitious, and that you really strive to overcome challenge. And I know that you often share with me, different biographical stories from magazines, something that you're reading in Esquire or GQ, or we will compare notes about Shackleton's journey to the Arctic.

Chas Lacaillade:

Yeah. Yeah.

Chris Erwin:

And I think these stories really resonate with you. I see this as a precursor to starting Bottle Rocket dating back 15, 20 years. Was there entrepreneurs in your family, your mother and father, siblings?

Chas Lacaillade:

Touching on what you were saying about these people that I've always been very impressed by, fortunately my parents exposed me to a lot of different ways of life. And I remember visiting William Randolph Hearst's mansion and just being so blown away by the scope of what this guy built, and how he lived, and his lifestyle, and the indoor pool and the outdoor pool. And all the art and architecture that he had imported from around the world, and how he'd customized this lifestyle. And so, I was so thrilled by that ambiance and the glamor of it. You know, how could I not be curious about how he provided this, and how he made this possible for himself? And so that lead me to familiarize myself with his accomplishments. And so once you know who somebody is and how they did it, and in this case he was very entrepreneurial, right? He created a newspaper empire and there's little he wouldn't do in order to achieve success.

Chas Lacaillade:

And so exposure to things like his mansion, or The Breakers in Rhode Island, and Providence, Rhode Island. I would go tour the Vanderbilt's mansions with my family in Rhode Island too. So just, I got exposure to these really impressive families. And my parents, my mother and father, would tell me how Cornelius Vanderbilt made his fortune, how he created a shipping empire. Or how Randolph Hearst created a newspaper empire.

Chris Erwin:

It's essentially made these stories accessible to you.

Chas Lacaillade:

Yeah.

Chris Erwin:

They grounded them in saying, "These are normal people-"

Chas Lacaillade:

Right.

Chris Erwin:

... "just like you and I, and so this is attainable if you have the spirit, and the intent, and drive to make it happen."

Chas Lacaillade:

Right.

Chris Erwin:

Is that like what you're processing of these stories and exposure?

Chas Lacaillade:

That's how I internalized it. It was also just like, "This is a pretty fascinating place. It's basically a museum, it's also a house. And it's indicative of a lifestyle that is pretty much bygone." And different people are going to take that in differently, but the way I interpreted the whole experience on all those occasions was like, "This is what's out there. If they did it, you can do it."

Chris Erwin:

I like that. Instead of looking at it and saying, "Oh, I can never achieve that," and then there's pangs of jealousy and frustration, it's, "Wow, if I hold myself big, there's incredible opportunity in front of me."

Chas Lacaillade:

Yeah.

Chris Erwin:

So let's fast forward. You find yourself in LA in 2006, and you're starting as an agent trainee at ICM Partners. So, what lead to the decision to join entertainment, overseeing and representing talent? Did you perceive it as, "This is the way to pursue your big ambitions"? Or, "Hey, this is just a key building block in learning, and I have a structured trajectory that I'm planning"? What was that thought process?

Chas Lacaillade:

Well, I'd always been really enamored with the world of entertainment, and Hollywood, music, they are areas that have fascinated me from a very young age. Consumed movies, and television, and music at a very high volume ever since I could remember, because I had an older brother and sister who could turn me on to different artists, and actors, and directors, and writers. So I felt like that was the path for me, and so basically I started my career out in an advertising agency in New York. Basically, I felt like I was spending a lot of time and effort at making a distraction and an impediment to what people really wanted, which was the TV show or the movie. I didn't want to make the advertisement before the movie, or the advertisement between blocks in the television show, I wanted to make the show or the movie.

Chris Erwin:

And just clarify for the listener, did you say that you worked in an ad agency in New York prior to ICM in LA?

Chas Lacaillade:

Yes. So my first job was at an ad agency that was called Euro Rscg, it's now known as Havas. It's like a worldwide advertising conglomerate. Then I worked on the Volvo and Charles Schwab accounts. I produced Volvo's first Super Bowl commercial, featuring Richard Branson. And I took a DVD of that and I sent it to the mail room basically, at ICM, and I got an interview and it worked out.

Chris Erwin:

And so you were at this precursor to Havas, for under a year?

Chas Lacaillade:

I was there for two years.

Chris Erwin:

So then you go to ICM-

Chas Lacaillade:

Right.

Chris Erwin:

... likely stars in your eyes, saying, "I don't want to just be the advertisement or the media spot, I want to help actually create the content."

Chas Lacaillade:

Oh yeah. You know, at ICM they wrapped Woody Allen, and Dr. Seuss estate, all these really luminaries like Halle Berry, Samuel L. Jackson, Guillermo del Toro, really famous directors and screenwriters. And was I so impressed by the luminaries that were represented at ICM, and I thought, "This would be a great place for me to gain experience and learn the ropes of the entertainment business." And it was.

Chris Erwin:

So the experience was what you expected?

Chas Lacaillade:

Yeah. You know, obviously you get a dose of reality. When you're young you don't know how hard it's going to be, and all the humbling moments that lie in store for you, and you want success much more quickly than it's likely to happen. And impatience can sometimes just frustrate how you're enjoying and processing things because you want more money, or you want more respect, or you want to be acknowledged, and truthfully, you're just another assistant, or you're just another guy fetching coffee. And you want to be seen as more than that, but until you prove yourself, you're not more than that. You are a means to an end.

Chris Erwin:

Something that is interesting about the agencies is that they attract ego, and I think it's something that they want. They want people coming in with confidence, with great ambition, yet at the same time there's a clear culture of, when you're there, you're in training mode, you have an incredible amount to learn. So you have to put that ego aside and say, "It's time to be a sponge." It's time to absorb from all these people that have been working for a lot longer than you have, so that you can then learn to be like, start to paint your own way. It seems like there's a unique duality there.

Chas Lacaillade:

I had a lot of ego and a lot of ambition, and I was humbled very quickly and-

Chris Erwin:

What was one of those humbling moments that you remember?

Chas Lacaillade:

I remember I had this really tyrannical boss, and there's no way I would've been able to accomplish what I did, subsequent to working at ICM, without his mentorship, but he used to tell me, "I'm your mentor and I'm your tormentor."

Chris Erwin:

That's funny.

Chas Lacaillade:

And he definitely did not go easy on the tormenting part. He'd tell me to do many things simultaneously, to the point where it was untenable. Like, he'd tell me to call a list of people, while composing letters to different clients, while scheduling his next lunch or his next dinner, and all of this stuff he would command me to do at that moment. At that moment. Which is physically impossible, but he didn't have any patience for any other alternative. And he also expected me to "be his brain." So he would be in the middle of conversations, he'd often have lapses of memory and he would snap his finger right before he began a sentence, which he was unsure if he could finish because he didn't know if he could remember the information.

Chris Erwin:

So, snapping his fingers is like an audio cue [crosstalk 00:11:12]?

Chas Lacaillade:

He'd snap at me hundreds of times throughout the day.

Chris Erwin:

No.

Chas Lacaillade:

So there's your first example of being humbled. He'd be on the phone with a client or a buyer at some studio and he would be embarking on this story, and he would snap at me and I would have to know what the next word in the sentence would be.

Chris Erwin:

You're expected to anticipate?

Chas Lacaillade:

Yes. And so he taught me anticipation. He made it crystal clear that if I couldn't anticipate his needs, then there's really no place for me working for him or at the company. You know, really top-tier client services anticipating what the talent is going to need, how the situation's going to present itself, how to navigate really difficult landscapes. And so, yes, it was self-serving for him because I was basically there to make him look good, but at the end of the day if you're a talent representative, you are there to make your talent look good. And so it was great training for that.

Chris Erwin:

I've heard a lot of the trainees and agents, sometimes they come from a place of fear about assuming the worst, so you always have to prevent or be in defensive mode.

Chas Lacaillade:

Right.

Chris Erwin:

But I think the best agents, and this is also good business practice for anyone is, you can also assume the best, and be opportunistic and say, "What's around the corner? What are people not thinking about? What are people not wary of that can be incredibly exciting for my talent? Can be incredibly exciting for my business?" As well as, "What is a major threat? What is a risk?" And I think, again, having that duality's important versus those that just solely come at it from a place of fear.

Chas Lacaillade:

Right. Exactly. And those are the people that succeed and rise most quickly, are the people who don't adhere to just status quo, and there's very few of those people in any industry. I remember being at a meeting and somebody saying, "You know which client at William Morris generates the most revenue?" And everybody thought it was Quentin Tarantino or Bruce Willis, and the person who posed the question said, "Emeril Lagasse." And he said, "This chef was unknown to most of the world five years ago, become a complete juggernaut, and has got all these lines of revenue. And the person who discovered him from William Morris and who's been helping forge opportunities for him, they're booking more revenue for him than anybody else."

Chris Erwin:

Wow.

Chas Lacaillade:

And that was an eye-opening moment for me, and that's something I really took close note of. And I thought to myself, "How can I go outside the confines of what everybody else is doing, and forge a path that will allow me to ascend higher?" I only had scant knowledge of him until that moment, and then of course first thing I did after that meeting was look him up. And then, "Who is my Emeril Lagasse? What is the avenue that's being unexplored right now?" And of course you're in a peer group that's incredibly ambitious, and incredibly intent on being successful, and oftentimes not generous with their expertise of information because any information that you get that is valuable, that diminishes their position and their value. And you're as valuable as what you know in that business.

Chris Erwin:

When you are entering markets where there is massive awareness about the opportunity, or where everyone is talking about it, there is less head room to grow into.

Chas Lacaillade:

Right.

Chris Erwin:

I think there's less profit and revenue to be created. And so it's time to be contrarian. It's also time to say, "You know, what is maybe not popular?" Or, "What is a risky bet, but that I'm going to take with the right amount of risk profile and I'm going to go forth?" And I think it's people and leaders that have that mindset, they usually have the biggest winnings.

Chas Lacaillade:

Right. But then, a lot of Hollywood's very traditional. The irony is that it's where all this cutting-edge entertainment and expression is generated, but at the same time the leadership and the hierarchy doesn't always encourage asymmetric thinking. And so, in fact, most people are incredibly defensive and incredibly insecure, and are adverse to taking risks. So, the only way you're going to be successful is by taking risk, and the least likely way to be acknowledged is by being different, so it's a struggle.

Chris Erwin:

You were at ICM Partners for a few years and then you left, what was the reason for leaving ICM?

Chas Lacaillade:

You know, I basically got a point there where, the WGA strike of 2008 was really tough, and that stagnated wages and it slowed everything down in the entertainment industry, in terms of opportunity and promotions. And you get to a certain point where you're like, "What am I doing to do with my life? I don't want to be just another person walking the halls here, slowly inching my way forward." And the culture at that time, it was just like, "Everybody, do what they're told." You know, that's pervasive culture, regardless of where you are. After four years of grinding and playing by the rules that had been laid out, it felt like it was time to just explore a different way of life.

Chris Erwin:

So, explore a different way of life?

Chas Lacaillade:

Yeah.

Chris Erwin:

So that seems to capture maybe a lot of things that happened over the next few years?

Chas Lacaillade:

Yeah. Yeah. So I'd always been very environmentally conscious, and really interested in sustainability and renewable energy, and I thought, "Maybe I'm not attaining the success I had always envisioned for myself at this stage in my life."

Chris Erwin:

Going back to the earlier part of our conversations where you're visiting the Hearst Castle-

Chas Lacaillade:

Right.

Chris Erwin:

... and learning about the Vanderbilts, and saying, "Wow, there's all this potential."

Chas Lacaillade:

Right.

Chris Erwin:

So you take a moment after a few years into our career, and you realize, "I don't have the success that I want." How did that feel?

Chas Lacaillade:

At that time I was 30 years old and I feel like if you're sane, you start to question yourself. I'm still a confident person, I'm still a very driven person, but I was beginning to wonder if my confidence and my drive were going to necessarily yield an impressive outcome, or any sort of meaningful outcome. Like, maybe I was just going to be just another guy locked into a 9:00 to 5:00 subsistence life? And maybe I wasn't as impressive and driven as I thought I was?

Chris Erwin:

Did that scare you?

Chas Lacaillade:

Oh, yeah. Definitely. That's a very unique kind of terror because it's not fleeting. It's not momentary. It's ongoing, doesn't leave you even when you sleep. It's with you when you're awake. It's with you when you're asleep. It changes your demeanor. It changes your outlook. It changes how people see you because you're questioning your very essence. You don't know if you're capable or, at that point, I didn't know if I was capable of doing what I always thought I was capable of. And so basically, at the same time I wasn't going to stop. You know, the only way forward was to push on.

Chris Erwin:

I think what you're getting on that's interesting is that, your planned trajectory and your fast rise had become part of your identity, that's how you knew yourself. And all of a sudden you're saying, "There could almost be a paradigm shift in my life. And if this is not my identity, then who am I-"

Chas Lacaillade:

Right.

Chris Erwin:

... "what's my purpose?"

Chas Lacaillade:

You know, I was used to being identified as keen, and hardworking, and talented, and then I had to look at myself in the mirror and say, "Well, if I'm those things, then why am I 30 years old and have a few hundred bucks in the bank?" Because people with those characteristic generally have a little bit more to show for them. And so I figured, okay, I'm running into a bit of a wall here, in my life and in my career, I need to do something where I can hopefully apply my drive and get something more out of it. And so, basically I got a job at a renewable energy company-

Chris Erwin:

Change industry's entirely.

Chas Lacaillade:

Change industry's entirely. And all these friends and family who'd seen you really work hard at something, in my case was in Hollywood, they say, "Good. Great." You know, "Happy for you," but you detect a little bit of doubt in their voice and you can't help but be unsettled by that. And you're 30 years old, I was 30 and I was like, "Oh my god. I'm basically starting from the bottom."

Chris Erwin:

Yeah. And I think that could also be a downward spiral where you think that there's doubt in your peer's voice about you, or their thoughts about you, but is that reality or is that just your perception and you're whipping yourself?

Chas Lacaillade:

I think it was reality, I think people were skeptical. But I would also say that, as you get older you realize that everybody's insecure about themselves, and so that could also be their lack of belief that they could do it. And so when they hear that you're going to switch fields, and you're going to do something completely different, in some cases what they're thinking is, "Well, I can never do that, so how's he going to do it?" Or, "I don't know anybody who's done that, how's he going to do it?" And what you need to take faith in is that, look, if you're determined and you have a game plan, it doesn't matter if they don't know anybody who's done it or if they can't do it, you can do it. Everything is doable. If there's a problem, there's a solution, so that's the way I approach things.

Chas Lacaillade:

And I got a job at a renewable energy company based out of Orange County, it was in Costa Mesa, and I had to commute from West LA to Costa Mesa five days a week.

Chris Erwin:

Wow.

Chas Lacaillade:

I mean, my office was essentially a garage in Costa Mesa, I mean, it was dark.

Chris Erwin:

So you show up-

Chas Lacaillade:

Literally and figuratively. And my peers were nothing like ... I wasn't interacting with these entertainment luminaries who are ... Tom Cruise wasn't on the phone. It was just basically old guys who were selling water pumps to plumbing warehouses, so talk about a total shift in gears. And my job was head of national sales, so when I wasn't in the office I was meeting with different plumbing supply warehouses and distributors throughout the nation, and getting them to carry our product, which I did very well. I increased the distribution and footprint of the product dramatically, like over 10 times. And I drove sales for this company, and I established a reputation with a group of people that I never thought I would know.

Chas Lacaillade:

And I say that I could not of started Bottle Rocket without my time working at ICM for that really hard boss, and I also couldn't have started Bottle Rocket had I not been head of sales for this company selling a product. It's a lot easier to sell a glamorous movie star to a studio that already wants to work with her, than it is to sell another water pump to a plumbing warehouse that has to carry it on the shelf.

Chris Erwin:

Did you believe that you learned these sales skills from any of your peers or the leadership at this company, or did you just have to figure it out on the go?

Chas Lacaillade:

You have to be open to your environment. You have to pick up cues. You have to see what people respond to. You have to read and listen to people who are experts in the field. So, there's a lot of sales manuals I read, and techniques I tried to pick and employ.

Chris Erwin:

Any sales seminars, weekend seminars, courses?

Chas Lacaillade:

No, I didn't do those so much, but obviously YouTube videos. And sales is so much about people and your relationship to people, and luckily I had developed an ability to really relate to a broad array of people, and broad range of people. And if you lead with sincerity and humor, generally, then at least you can open up somebody's receptivity to whatever message you want to convey.

Chris Erwin:

And the fact that you were looking at YouTube videos back then, it's just interesting to think about where you then went next.

Chas Lacaillade:

Right, isn't that funny. Yeah.

Chris Erwin:

Because you ended up at Fullscreen, but did you go right to Fullscreen, a multi-channel network, after selling water pumps, or was there another stop in between?

Chas Lacaillade:

Basically, I'd been working at this restaurant in West Hollywood all the while, just to pick up extra revenue. So I was definitely hustling, hustling hard to made ends meet.

Chris Erwin:

So you're full-time and part-time work in this period?

Chas Lacaillade:

Yeah. I had an epiphany when I was on a sales trip to Louisiana, and I was driving around the Bayou of Louisiana with this manufacturer's rep who was my conduit in Louisiana, distributing the pumps, and he said, "What did you used to do before you were selling pumps?" And I told him about my career at ICM. And he said, "Hold on. You and I are driving around Louisiana in 95 degree heat, trying to sell friggen water pumps, and you used to talk to movie stars and screen writers? What the hell is your problem?" He's like, "I would give up everything to start at the company that you left." He's like, "If you can leave this and go back to that ... And if you don't love this, which nobody does ..."

Chas Lacaillade:

He's like, "This is a means to the end. I put food on the table for my family, myself. I've got a daughter and this is how I pay for my life. You don't have any of those commitments. You're not married. You're single. You're young enough to go back to it." He's like, "If you love it like it sounds like you do, go back." This guy's name was Dustin [Ubray 00:23:08], shout out to Dustin Ubray.

Chris Erwin:

Thanks, Dustin Ubray, for pointing Chas on his new path.

Chas Lacaillade:

Yeah, and-

Chris Erwin:

So you hear this-

Chas Lacaillade:

And I'm like-

Chris Erwin:

... and what goes through your head?

Chas Lacaillade:

And I'm realizing like, you know what? I'm always going to care a lot about the environment and sustainability, but the real truth is, this is not the life I envisioned or that I want. And I was open to it and I gave it a go, but I don't see this unfolding in a way that's going to make me happy. And it's always important to explore things and really give them a sincere look, but if it doesn't feel right, you cannot be reluctant to pull the ripcord. And a lot of people are scared of starting over, and so much of success boils down to your ability to start from scratch and just persist.

Chris Erwin:

So in that moment, did you feel any regret where you were like, "Oh my god, I made this big change in my career and it seems that it was off to the wayside, and now I've got to get back on track"? Or did you interpret it as, "Wow, this was a really special moment, I learned a lot, and now I'm going to go back into entertainment, find a new opportunity space, but I'm further energized to do it"?

Chas Lacaillade:

Yeah.

Chris Erwin:

What were you feeling?

Chas Lacaillade:

Well at that point, so now I'm 32, and I'm like, "Okay, the sand's going through the hourglass on me, and I'm going to do another pivot to I don't know where. I don't know who's going to hire me." And I've got some explaining to do next time I sit down at an interview because I've got some accomplishments under my belt, but they're two wildly different and divergent fields. So people are going to be curious, some people are going to be skeptical, and I'm going to have to prove myself in the room and I'm going to really have to prove myself ... if somebody gives me a chance, I'm going to really have to bust my arse for them to have faith that they made the right decision.

Chris Erwin:

But you had confidence that you were going to be able to do that?

Chas Lacaillade:

I had confidence I was going to be able to do it, but back to what we were discussing with people not wanting to take risks, HR departments are not known for being open-minded. They want to look at that resume and they want to see identifiable qualities that will give them insurance if they make a hire that doesn't work out. And so, I didn't have this, and so what I depended on was getting in the room. It was like, if I get in the room, I've got a strong chance at getting the job, but just getting in the room is tough.

Chris Erwin:

How did you get in the room for Fullscreen?

Chas Lacaillade:

I had a-

Chris Erwin:

Did you pick them or did they pick you?

Chas Lacaillade:

I had a really close friend from ICM who was best friends with the head of production at Fullscreen, and Fullscreen was a startup, and they had-

Chris Erwin:

Yeah, what was Fullscreen, for our audience?

Chas Lacaillade:

Fullscreen was a multi-channel network known as an MCN, which is basically, Fullscreen's raison d'etre was "we are going to collect a broad range of YouTube channels, and sell advertising against those YouTube channels." That's a really broad overview of what they did. And so the money that Fullscreen made was, the revenue source, was advertising on YouTube.

Chris Erwin:

Got it.

Chas Lacaillade:

That's how they made money. They had a few dozen employees. They had some venture capital investment from Peter [inaudible 00:25:59]. So yeah, a good friend of mine knew they had production there, had a production. Put my resume in the mix for a role, I went in to interview, they needed somebody just to work with these YouTuber's. I had a background in entertainment and I really, really emphasized that.

Chris Erwin:

Yeah.

Chas Lacaillade:

And my background was legitimate, and it was quality, and I had worked with a lot of people, and I had good references.

Chris Erwin:

So you had ICM on your resume-

Chas Lacaillade:

Yeah.

Chris Erwin:

... that's instant pedigree in entertainment.

Chas Lacaillade:

I had references, and if they wanted to call anybody, that a lot of people liked me or were fond of me, and my work ethic was there. So at that point, a lot of people from the traditional entertainment world didn't respect YouTube, and didn't see it as a viable commercial avenue.

Chris Erwin:

And why do you think that was?

Chas Lacaillade:

They basically regarded it as a distraction, as not a competitor to TV, and radio, and film. And just for very low cost entertainment that people didn't pay for.

Chris Erwin:

Yeah. One of the things that I heard myself, because I was also part of the multi-channel network eco system where I first started, big frame, a wish like Fullscreen had, venture capital backing, and then also had funding from a Google originals channel program, from Google itself, and then on to AwesomenessTV. And from a lot of traditional Hollywood they would say, "These digitally native creators, they're not used to hearing the word, no. They just had this unique moment in time where they started publishing videos on YouTube or a social channel, and then they got famous." And it felt very strongly that unless you were in the annals of these MCNs, or working with these next-gen talent, you don't understand the amount of hard work, the amount of time and the commitment to the audiences that they created for themself, and the brands that they created for themself. So, I hear you on that.

Chris Erwin:

Chas, you're at Fullscreen and this is the job that you had right before founding Bottle Rocket, and remind me what was your role while you were at Fullscreen?

Chas Lacaillade:

I was the head of talent sales.

Chris Erwin:

Was this a division that you actually founded at the company?

Chas Lacaillade:

Yes. So basically what happened at Fullscreen was, I was hired to be a "talent manager," and we had a sales department and division at Fullscreen. You know, I was talking to the talent, I was working with these YouTubers. This is early, this is 2013. They would get offers to promote products for 5,000 or 2,500 bucks, and the big YouTuber's case like $10,000, and I said, "You know, I've got experience in talent representation, let me secure and negotiate these opportunities for you." So I close a deal for a talent to promote a product, and sales caught wind of what I was doing, the sales department, and they said, "Listen, it's not your role to do any sort of sales activity here at Fullscreen. We are the division and the department that's dedicated to that. And the threshold for any deals that our talent participates in is $50,000. If it's not $50,000 or above, it's not worth Fullscreen's time. You know, if it's less than 50K, we pass on it."

Chris Erwin:

So, they're telling you to stay in your lane-

Chas Lacaillade:

Right.

Chris Erwin:

... and here's your lane by the way, what this looks like, and let us do our thing?

Chas Lacaillade:

And if it's less than 50K, decline. And I said, "Well, there's a lot of money between $1 and $50,000, we're leaving a lot of money on the table, and that's really important for our clients, that's how they pay their bills." And they said, "Listen, if it gets to 50K, hand it over to us and we'll take care of it." Kind of a pat on the head. And I found that incredibly shortsighted, and I was not deterred for a nanosecond. And I-

Chris Erwin:

Yeah, let's focus on that for a second. So, not deterred. So, other people might hear that feedback, get really frustrated, but then just say, "Okay, I've been told to stay in my lane, this is what I'm going to do." But you did not react like that. Was it potentially a catalyst for you?

Chas Lacaillade:

Yeah. No, it absolutely was. So I'm like, "I know how to do this. I see the opportunity here. These people are really creative, they have really large audiences. They've got a really special unique relationship with that audience, and this is something that nobody's doing, so I'm going to do it." And I went up to the business affairs office. I was on the second floor and I said, "Please make me a two-page template that I can repeat and just swap out names, and print out information." They made a two-page deal template for me, and I proceeded to create my own world basically, and owned a division, an army of one, where I would source a deal, secure and negotiate the deal, and close it, and invoice for it, and Fullscreen's 10% would just go to Fullscreen's accounting department. And the sale division didn't like that, but I was providing a service to all the talent that was in the network, that became undeniable.

Chris Erwin:

Now you're running around as a team of one-

Chas Lacaillade:

Right.

Chris Erwin:

... was this exciting for you, while also-

Chas Lacaillade:

Yeah, absolutely.

Chris Erwin:

I mean, it must have been awkward at the same time because then within the same walls of the building, there's people frustrated with your behavior, yet you're like, "Wow, I just found this goldmine and I'm going after them."

Chas Lacaillade:

Yeah, I didn't care about them. You know, they weren't my friends and I wasn't impressed by them professionally. I didn't think that they were good at their jobs. I didn't think they knew their product. To be an effective salesperson you have to know our product, and none of these people watched YouTube, none of them had relationships with the YouTubers that they were tasked with selling.

Chris Erwin:

Got it.

Chas Lacaillade:

To work in this space, you have to be able to pick up the phone and call the talent and say, "I've got this opportunity for you, is this exciting to you? How would you integrate this product into your content?" And you have to have a conversation with them. And if you don't any sort of rapport with that talent, then good luck. And so, I had developed a rapport with this talent. I knew how advertising worked. I could speak that language very fluidly, given my experience at the ad agency in Manhattan. I also knew how to deal with talent via my experience at ICM. I knew sales, via my experience at the renewable energy company.

Chris Erwin:

It's like all this is coming together.

Chas Lacaillade:

So all these three really separate experiences unified in this really elegant tapestry, that set me apart, made me unique from my peers at Fullscreen, and allowed me to really confidently stake out my claim, and so that's what I did. At this point I'm 32 years old. Had I been 25, I might've been a little bit more intimidated. But because I knew what I was doing, I had a very clear vision for the future and how I was going to use my skillset to drive value and create value for the company, I was able to rebuff all the feeble pleas and objections that were being posed by my peers who were threatened.

Chris Erwin:

Did this moment feel like a very unique inflection point where all my past career experience, my capabilities, my learnings, my mindset, it's like, "This is happening now in my early 30s." Going back to that identity of "the world is my oyster." Right?

Chas Lacaillade:

Mm-hmm (affirmative).

Chris Erwin:

It's like what you were thinking when you were in high school in your early days.

Chas Lacaillade:

Right.

Chris Erwin:

And did you feel like in this moment it's like, "This is it"?

Chas Lacaillade:

Yeah. So it did feel like that, and I felt like, "Look, the money's not big now, but everything has to start from somewhere." And also, I was synthesizing all of those biographies I'd read of Sam Walton starting out Walmart with just a Five and Dime store here, or then he built to three "Five and Dime stores in Arkansas and Memphis, and these outposts that were in these rinky-dink towns, but no one else was building there. And what I felt was, I'm building stores where no one else is, and I'm going to get customers that no one else is going to get. And by the time that everybody wakes up, I'm going to have more stores than anyone else. And so I moved very quickly and I thought, "Look, I don't know where this is going to go, but this is something that's valuable, and interesting, and engaging, and I'm developing a reputation internally as somebody who's got a clear point of view." And people are attracted to and drawn to someone with a point of view and an idea on how to create value.

Chris Erwin:

It's clear that you are no longer at Fullscreen.

Chas Lacaillade:

Right.

Chris Erwin:

You now are at a company that you founded, Bottle Rocket Management.

Chas Lacaillade:

Right.

Chris Erwin:

When did you found Bottle Rocket?

Chas Lacaillade:

So AT&T bought Fullscreen in 2015, and at that point Fullscreen was not intent on being in the talent representation business and I was. And I had my Jerry Maguire moment where I called all my clients and said, "Am I your manager? Am I your manager? And if so, this is my new endeavor, I'm going out on my own."

Chris Erwin:

Was that scary to do that?

Chas Lacaillade:

It was terrifying. I took out a $5,000 loan from Chase Bank, and there was no interest for the first 18 months.

Chris Erwin:

And what was that loan for?

Chas Lacaillade:

To live. So-

Chris Erwin:

Pay rent, food-

Chas Lacaillade:

Pay rent, my rent was $1,200 a month, so I figured I could get by for a quarter, three months-

Chris Erwin:

Wow.

Chas Lacaillade:

... if I just had one meal a day, didn't do anything on the weekend, no bars or entertainment, or movies. Basically, ate one meal a day, and paid my internet bill, and paid my rent, I could get by for three months.

Chris Erwin:

So this is extreme focus.

Chas Lacaillade:

Yep.

Chris Erwin:

Your job during these three months is, I got basic financing in place and now I'm going to build a company, and it's going to win. And you have your horse blinders on?

Chas Lacaillade:

Yeah.

Chris Erwin:

What happens over those three months?

Chas Lacaillade:

And so, I was able to pay the $5,000 back within 45 days-

Chris Erwin:

Wow.

Chas Lacaillade:

... and had no debt, and I'd closed enough deals that I knew I was going to make enough money to live in that year, in 2015. So, Bottle Rocket started March 1st, 2015 and all the clients I represented at Fullscreen formally, decided that they wanted to line up with me and I built a business. So from a one-bedroom apartment in Venice, I just sat there and called people all day.

Chris Erwin:

You knew 45 days in, you had something?

Chas Lacaillade:

Yes.

Chris Erwin:

You look at your business now, the business that you have from a revenue point of view, and volume point of view, is a lot larger than a lot of other next-gen management companies. What was that next inflection point where you're like, "Okay, I don't just have something here, I have something really special"?

Chas Lacaillade:

I think it's when I started needing to bring on staff. You know, I'd been doing everything by myself.

Chris Erwin:

And when was that?

Chas Lacaillade:

It was 2017, and now we've got a staff of five, including myself. You know, what I'm really thrilled about it how busy everybody is, and how the environment feels really entrepreneurial, really light. I feel like if you have a sense of lightness within the company, and joy, that people are going to put forth discretionary effort, they're going to give you that extra ... whether it's talent, or whether it's the buyer, or whether it's your own colleague, if they know that you're coming from a place of reason and you're a good person, you're just going to get more out of everything and everybody. Now, there's a lot of challenging encounters, there's times when points of view collide and you still have to be firm, and you have to have faith that your position is legitimate. And perhaps somebody wants something from you or from your client that is unreasonable, that's where the challenge is. How do I create customer delight and value for this person, whilst still maintaining my position?

Chris Erwin:

As you think about how you energize in your business, and you continually refine your leadership and your management philosophy, how do you do that? Is it through reading? Do you have like a mastermind's group? How do you come into your business every day and push yourself to be better for your clients?

Chas Lacaillade:

Personally for myself, you've got to nurse your mind with new points of view, and you've got to read, and you've got to stay current. Personally, I read the Wall Street Journal, which is not exactly cutting-edge technique.

Chris Erwin:

While on the bike at the Bay Club?

Chas Lacaillade:

Yep. Yep, I read the Wall Street Journal every day. One of my professors at USC Business School said, "If you want to be smarter, read The Wall Street Journal every day." Very simple piece of advice and I took it to heart, and I feel like it's very helpful. You know, basically I want to get information from places that aren't the internet. You're definitely a more well-rounded individual if you're not just sighting whatever was on Apple News that day. So I read the newspaper every day. I read fiction and nonfiction. You've got to keep your vocabulary relevant and sharp, and your mind dynamic, and reading different pieces of information and literature, it helps you do that. Because so much of being interesting to others, is being interested in what other people are doing and how the world's working. And so, if I'm interesting to my peers and people that I want to do business with, then that's already a head start in the right direction. And so, that's how I keep it fresh.

Chris Erwin:

You raise a good point because if you're just reading the same industry pubs that everyone's reading, which it's good to be current, but if you're just in Variety, and Hollywood Reporter, and Tubefilter all day, you're not giving your mind space to breathe. And so when you say, "Mind, body, spirits," so it's out of being an avid reader, how do you also energize your body and your spirit?

Chas Lacaillade:

You know, sometimes I surf, as you know. I play soccer at a rec sports league. I play basketball with some friends occasionally. I'm very active, it's just important to me to be out there moving. And the spirit and the body are very closely linked, so I feel like if I'm running or playing a sport, then my spirit is being nourished.

Chris Erwin:

I'm not sure if you're going to enjoy me sharing this story, but yes, Chas and I, we have skied together many times at Sundance and Park City. We've also surfed many times here in LA. And I will say, I think the last time that we went and surfed at Malibu at Second Point, Chas was really excited to get in the water, he hadn't been in in a bit. As we're walking to the beach, I just look at his surfboard and I'm like, "Okay, there's normally three fins on a surfboard, but I only see two on yours, Chas. What's going on?" You're like, "Yeah, it's immaterial, don't worry about it." I'm like, "Okay," thinking you need three fins, but all good. Then we get to the beach and Chas says, he's like, "This wetsuit is so uncomfortable, it's so tight in all these weird places. What's going on here?" I'm like, "Is this a new wetsuit? You've had it before, right?" He's like, "Yeah. No, it's the same one, but this is just weird."

Chris Erwin:

I thought to myself and I was like, "All right, I remember a similar conversation the last time we surfed." And then I look over at Chas, right before I say it, Chas says it, he goes, "I think this wetsuit's on backwards." And so the suit was on backwards, but what I loved was that instead of Chas being like, "Oh, I'm going to go walk back to the car and change it," or, "I have to go get another fin," you were just like, "I'm getting in the water. I'm fine. You know, I don't care what people think, let's go," and we went right into it. And I think that was a great reflection of how you approach life-

Chas Lacaillade:

Yeah.

Chris Erwin:

... and business, and friendships. You're just like, "I'm doing what I'm doing, and I'm happy with it-"

Chas Lacaillade:

The wetsuit-

Chris Erwin:

... "and I don't care what anyone else thinks."

Chas Lacaillade:

The wetsuit being on backwards is not going to change the waves.

Chris Erwin:

Yeah, exactly.

Chas Lacaillade:

The board's there, the wave's there, I'm here. All the necessary elements for me surfing are present, so ... I was in the water and some dude's like, "Your wetsuit's on backwards." I was like, "I'm clear on that. I know that." I think I spaced out in the moment, I think I was caught up in conversation. Hadn't had my caffeine dose and idiotically put my wetsuit on backwards, but then I was just like, "Ah, you know what?-"

Chris Erwin:

Maybe it's a reflection-

Chas Lacaillade:

... "It's not going to slow me down."

Chris Erwin:

You're so in the moment and you're so present, you didn't even know your wetsuit was on backwards. You know, so maybe that's a good thing, maybe more people need to have that happen to them. All right, so before we get into our rapid fire round, last question on Bottle Rocket. What are some of your 2020 goals for Bottle Rocket and the team? What do you look forward to?

Chas Lacaillade:

I want to develop relationships with new buyers that we haven't worked with previously, that's really important to me. You've got to keep exploring opportunity with the marketplace and developing new relationships. And then, definitely signing new talent that's exciting and dynamic, and that's going to raise and elevate the perception of Bottle Rocket. And hopefully growing the Bottle Rocket team, so that I continue to have peers that inspire me and feel energized to come to work.

Chris Erwin:

When we talk about new talent, because we were talking a bit before this, you're not just a digital talent management company, you're next-gen. To prove that point out, you've signed traditional talent, you've signed also writers, you've diversified across your entertainment roster. Which I think is great and it's interesting to see how when you have that diversity of talent, they can work and collaborate with one another-

Chas Lacaillade:

Right.

Chris Erwin:

... which really fuels your own internal business. But are there any certain types of talent that you are specifically seeking out in the new year?

Chas Lacaillade:

What I want to identify and what I'd love to represent, are people with really unique points of view and unique skillsets. YouTube, there's a lot of derivative content on YouTube, and herd mentality is pervasive in all forms and genres of entertainment and media. But when you really strike gold is when you've got that person who galvanizes an audience because of who they are and how they see the world, and how they interact with the world. The Will Smith's of the world, ELiza Koshy, Ellen DeGeneres, Oprah. And so you want to find that person or people who have a magnetism about them that's undeniable.

Chris Erwin:

Well, we wish you a very prosperous 2020.

Chas Lacaillade:

Thank you. Thank you.

Chris Erwin:

So, we'll go into the closing rapid fire questions, how's that sound?

Chas Lacaillade:

Great.

Chris Erwin:

All right. So these can be just quick, two to three sentence answers. If you want to be even more brief, we're open to that. Looking back on your career, what would you say your single proudest moment and accomplishment is to date?

Chas Lacaillade:

The day I started Bottle Rocket Management, March 1st, 2015.

Chris Erwin:

What do you want to do less and more of in 2020? Let's start with less.

Chas Lacaillade:

Worry. Worry, there's no form of progress when you're contemplating what's going to go wrong, or whatever may happen will adversely affect you. You've just got to believe.

Chris Erwin:

Rapid fire follow-up to that, what do you worry about the most?

Chas Lacaillade:

Delivering for my clients and my team.

Chris Erwin:

What do you want to do more of in 2020?

Chas Lacaillade:

Well, I definitely want my team to feel inspired and really excited to be at Bottle Rocket. And I want them to have personal wins, so that they feel like it's not just a company where they work for me, it's where they work for themselves and they're developing their own reputations.

Chris Erwin:

Entrepreneurial advice. What one to two personal characteristics do you think have primarily driven your success?

Chas Lacaillade:

Say, persistence. Persistence is definitely the main identifiable characteristic that's helped me. And humility, just accepting that you're going to have to prove yourself and people aren't going to hand you the biggest, juiciest opportunities off the bat. And so, you have to be humble and prove yourself.

Chris Erwin:

We talk about persistence a lot, where there's ebbs and flows in the business cycles and your own individual business, and with your team, but if you just are always showing up everyday, there are going to be these incredible moments for you to take advantage of. But if you're not showing up, it's not going to happen. Last few questions here. How do you best take advantage of things you can't control?

Chas Lacaillade:

I think you've just got to be clear. You've just got to figure out what your position is and how you see things. Articulate that to whomever is necessary, and be open-minded.

Chris Erwin:

Okay, last two. Quick shot advice for media professionals going into 2020?

Chas Lacaillade:

Try to schedule as many meetings with people that you're curious about, and want to meet and want to know, and sit down with them wherever they are, and make yourself available.

Chris Erwin:

Last question. How can people get in contact with you, Chas, the CEO and founder of Bottle Rocket Management?

Chas Lacaillade:

My email address is [email protected], spelled out.

Chris Erwin:

We'll also include that in the show notes.

Chas Lacaillade:

Excellent.

Chris Erwin:

Well, this has been a delight, Chas. Great to have you in today.

Chas Lacaillade:

Thank you.

Chris Erwin:

See you around at the next surf sess.

Chas Lacaillade:

Right on.

Chris Erwin:

Wow, I really enjoyed that conversation with Chas. Like I said in the beginning, he is a total straight shooter and tells you like it is, and that really came across. I don't know if you guys felt this, but when he started talking about founding Bottle Rocket and leaving Fullscreen, in the room you could see and you could feel his energy just ramping. It was exciting. I thought that was a pretty special moment in our conversation. The excitement of an entrepreneur. So a few quick things on your radar, our next podcast will feature Christian Baesler, the President of Complex Media. He is a young media savant, with a very impressive career track record. Fun facts about Christian, he was born east of the Berlin Wall, and in the same week that the week came down. Pretty incredible. And when he was right out of college at a big international media company, he was tasked with overseeing a digital division, and they needed a digital website network to be built, Christian just built it himself. Impressive stuff.

Chris Erwin:

Second thing on your radar, listeners, is that our company RockWater, will be hosting a live stream media and selling conference in 2021. Likely in the first quarter in March, we don't know exactly what it's going to look like yet, but we will bring together great speakers, good programming, and we're looking for people who want to get involved. So if you're interested, you can email us at [email protected]. Stay tuned for that. All right, that's it. Thanks all for listening.

Chris Erwin:

The Come Up is written and hosted by me, Chris Erwin, and is a production of RockWater Industries. Please rate and review this show on Apple Podcast. And remember to subscribe, wherever you listen to our show. And if you really dig us, feel free to forward The Come Up to a friend. You can sign up for our company newsletter at wearerockwater.com/newsletter. And you can follow us on Twitter @TCUpod. The Come Up is engineered by Daniel Tureck. Music is by Devon Bryant. Logo and branding is by Kevin Zazzali. And special thanks to Andrew Cohen and Sean Diep from the RockWater team.

Adam Sachs is the COO of Team Coco and a veteran podcast and digital media executive. Adam works with some of the biggest names in Hollywood like Conan O'Brien, and even Barack and Michelle Obama. We discuss his time as CEO of Midroll Media and its sale to E.W. Scripps, founding a group dating website that he sold to IAC, and the power of being foolishly confident. Full episode transcript is below.

Subscribe to our newsletter. We explore the intersection of media, technology, and commerce: sign-up link

Learn more about our market research and executive advisory: RockWater website

Follow The Come Up on Twitter: @TCUpod

Email us: [email protected]

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EPISODE TRANSCRIPT

Chris Erwin:

Hi, I'm Chris Erwin. Welcome to The Come Up. A podcast that interviews entrepreneurs and leaders.

Adam Sachs:

I think we were foolishly so confident. We just thought, "Oh, we have a great idea, so it's going to be successful. Let's just quit our jobs and start this business." And didn't really understand that so much has to go right in order for it to be successful. And not only does so much have to go right, but it takes so long.

Chris Erwin:

This week's episode features Adam Sachs. Adam is a true digital media OG. And today he works with some of the biggest names in Hollywood, like Conan O'Brien and even the Obamas. So we got a lot to talk about. We'll get into how he started a group dating website and then moved his family to India for it and sold that to Barry Diller. Then we'll talk about how Adam joined as the CEO of Midroll Media, and then orchestrated its sale to E.W. Scripps, one of the biggest deals in podcasting at the time.

Chris Erwin:

There's many other stories in between. Adam's a fantastic guy. This interview is a lot of fun. Let's get into it. Quick heads up that my interview with Adam was recorded back in January and prior to COVID. 

Where do you think your entertainment and comedy origins really starts?

Adam Sachs:

I don't know. I've always been obsessed with comedy from a very young age. I was obsessed with Adam Sandler and then Jerry Seinfeld, and Seinfeld the show was a really important part of my life. At one point, I think I could recite every word of every episode of Seinfeld. I would just watch the tapes over and over and over again. And the same for Adam Sandler movies before that. Yeah. I don't know.

Adam Sachs:

I just always loved it. And the idea of having a career in comedy, I didn't really know what that would be, but I always wanted to have a career in comedy. And at points I thought, "Well, maybe I'll be a comedian." I never really was I think, talented enough to do that.

Chris Erwin:

I always remember you as being kind of like a class clown and very funny and very witty and always, like you said, sightings really funny, like Seinfeld references and jokes for everything that we did. But it seemed like you started to take it more seriously when you're like, "Okay, I'm going to join the improv jam in Red Bank." When you started doing that, did that further solidify your like, "Yeah, there's going to be a future for me here." Or you're like, "Oh actually, maybe this is not for me. This is harder than I thought."

Adam Sachs:

I really enjoyed it. But I was also never one of those people who was super comfortable on stage. I think what I realized after I started doing these improv classes at the local internet cafe, but I did love it. And I thought that the people around me were really talented and I really enjoyed that. And so yeah, even going into college, I thought, "Oh, maybe being on stage isn't really for me, but maybe I'll be a comedy writer. Maybe I'll write TV shows like funny TV shows."

Adam Sachs:

And I did pursue that. I had a regular college education, and at one point thought maybe I'll end up going to law school and even studied for the LSAT. That was sort of like a hedge, I think, because in parallel I had like a writing partner who I went to college with, Ally Hord who still a good friend of mine and we would write comedy scripts together. And she was the more talented one. She went on to be successful.

Chris Erwin:

I think you guys are both incredibly talented with great success.

Adam Sachs:

No. She is really, really funny. And now she's a writer at Seth Meyers.

Chris Erwin:

I remember Ally Hord. I think I was working because Adam and I both share a Northwestern Wildcat blood. And I was working on a startup idea when I was in grad school there. And I think I had asked Ally who was at Funny Or Die at the time. I was like, "Oh, can you be a beta tester of my product?" And she was always very supportive, and she was like, "Oh yeah, we're using it. We're using it on set. It's super helpful."

Chris Erwin:

And I don't think they actually really did anything with it, but she was a great sport. All right. So you're at Northwestern, you decide that you're not going to go to law school. And so instead of doing that, you decide to teach English abroad as your first move right out of undergrad. And what was the reason for that?

Adam Sachs:

I had a friend Howie who's a year above me who he is now a lawyer, but he was also like not sure if he wanted to be a lawyer or what do you want it to do. And he went to Madrid and he and I were really close. We stayed in touch and it sounded really cool. And I didn't know what I wanted to do. I had taken the LSAT. I didn't know if I wanted to go to law school. In my gut felt like I didn't really want to go to law school, but I wasn't sure. And so I was just decided I'll just take a year and like go abroad and maybe I'll figure it out.

Chris Erwin:

It's almost like in a way a lot of kids now are taking a gap year before they go to school. But getting some free mental space to be like, what do I really want to do to reflect, be exposed to new experiences? And I think a lot of people should do that more often in their careers and more often in their life. And don't. And I remember that you were telling our group about that. I'm like, "Well, Adam has always such an ambitious focus person. Is he already falling off the wagon?"

Adam Sachs:

I felt like that, to be honest. First of all, going abroad is like, it was a huge privilege. I made a little money teaching English, but not everyone can do it. I don't think, but it was like, I look back on it and yeah, halfway through it, I was like, "My friends are already ... they already have jobs. I'm really falling behind. What's happening here? My college friends are like getting jobs at like JP Morgan or they're in law school or whatever it is."

Adam Sachs:

And I'm like, "What am I doing? I'm going to be so far behind all of my peers when I get back after this year." And that now looking back, like in retrospect, that was dumb. I shouldn't have been worrying about that because it was an enormously formative experience in my life because it was like I was able to see a lot of the world and meet a lot of people and just gain perspective that I wouldn't have gotten otherwise. And I still have really close friends from that period that live in Madrid or live in Prague.

Chris Erwin:

No. And that's interesting to hear that you had doubts during that period. But at the end of your year of teaching English as a second language, were you starting to feel comfortable like, "No, this was actually the right decision. I've learned a lot."

Adam Sachs:

Maybe. Now I feel like it was a right decision. At the end of that year, I don't know. I still felt like I got to get back. I have to get home and like start doing something so that I'm not the bum.

Chris Erwin:

Yeah. And that's a theme throughout your career narrative is that you've made decisions where I've looked at them early on, was like, "Oh, Adam's going and teaching abroad. That's kind of a weird move right out of undergrad." And then, "Adams he's starting a tech company and is applying to Techstars. What is that? Startups aren't cool yet." And it was always kind of like this contrarian approach where there was probably like doubt within you, but doubt within the peer group. But it's clear that all of these buts have really paid off. Kudos to that.

Adam Sachs:

Maybe. You're giving me a lot of credit. We'll see where all this goes.

Chris Erwin:

Okay. So after abroad, you decided to go to Sony. How did that come to be?

Adam Sachs:

I knew people at Sony from my internship, so I reached out to them and I got a very kind of entry level job in Sony Pictures Television in New York.

Chris Erwin:

And did you feel that when you were doing that because your career took a big turn when you started your first company soon after, or maybe concurrently while you were at Sony. Did you look at Sony as, "Hey, this is something I want to invest material time into," or is this, "This is just a stepping stone. And I want to get maybe that traditional validation of working at a big company."

Adam Sachs:

To be honest, I think at first I thought I'll get my foot in the door of this like really great company. Everyone that was a radio TV, film major at Northwestern, if they didn't go into being a writer or director or pursuing that path, if they went into TV, the hot thing was like to go into development. And I was like, "I think I want to go into development." I didn't even know what it meant really.

Adam Sachs:

I was just like, "But it sounds cool to be a development executive." And I think I applied for those jobs and I didn't get them or whatever. So I got like a different job in the ad sales department at Sony. But I think my thinking was, I'll get in the door there and then I'll figure out how to have a development career. And hopefully along the way, I'll figure out what development means. So, that was my thinking.

Chris Erwin:

I think I want a development career. I don't know what it is, but it's sound has cache.

Adam Sachs:

But it sounds cool. And people who do it think it's cool. So I honestly think that was my thinking at the time. And there was also always a New York, LA kind of conflict in my mind. This was in New York, but I did feel like LA was an inevitability at some point if I wanted to pursue that sort of career. But at the same time, my good college friend and I, Dan Osit, we started to talk about this startup idea that we got, that we've got really obsessed with.

Adam Sachs:

And it was the idea of, we were in our early mid 20s living in New York City and going out with our group of friends and going out and meeting other friends. And we started to think, "Man, isn't it crazy that there's no dating site that were like, you go out with your friends and meet other people. And wouldn't it more fun and less awkward and even safer to have an experience where you went out with your friends and met another group of friends."

Adam Sachs:

And the more we talked about that idea, he was also in his first or second year of working in a finance job out of college. The more we talked about that idea, the more we thought like, this is a really good idea. And we talked to friends who thought it was a good idea. And I think I was planning to move to LA and move in with Matt and Rob and some of our buddies and just figure out like how to get a development job basically.

Adam Sachs:

But then I became obsessed with this business idea and this idea of starting a startup. And the more we talked to our friends, the more we got excited about it. And then we quit our jobs and we started pursuing it.

Chris Erwin:

So how'd you guys think about how to start actually building the company? Today feels like there's millions of guides for like how to build a business. But 15 years ago, there was a lot less resources out there. So what did you guys turn to?

Adam Sachs:

Here's how different the landscape was then. We sent an email, Dan and I sent an email to like all of our friends, like a blast email being like, "Does anyone know anyone who has ever started a company because we don't know where to start?"

Chris Erwin:

I may have been on that email.

Adam Sachs:

I'm sure you were. And we got like one response or two responses, and we ended up meeting the guys who started meetup.com, which was a really good connection for us. But today, if you ask that question, everyone knows someone who has started a startup.

Chris Erwin:

The Lean Startup, Four Steps to the Epiphany, like all of these books.

Adam Sachs:

Exactly. And that stuff didn't really exist. Or if it did, we were unaware of it. It was like, there was a less of established path at that point because we didn't know what to do. We said, "Okay, we want to start this thing." But what if we had literally just had to try to start taking people out to coffee to understand how do you do this?

Chris Erwin:

Yeah. So what was the point where you guys made that decision, we're leaving our jobs, we're getting off this path to become development execs, whatever that is, or financiers? That is a big decision to make at an early age. Also considering like what your peers are doing, your parents probably not understanding the opportunities within the startup space. What was that catalyst point?

Adam Sachs:

I think we were, and to be honest, like foolishly so confident that we had a great idea. And I think because we knew so little about starting a business, didn't realize how important execution is. And we just thought, "Oh, we have a great idea. So it's going to be successful of course, because our idea is great. And we've asked our friends and they think it's great too. So let's just quit our jobs and start this business."

Adam Sachs:

And didn't really understand that so much has to go right in order for it to be successful. And not only do so much have to go right, but it takes so long and it's going to take a lot of endurance. But it was not easy. Like my friends all continued on in their jobs in New York City. I had to move home. I didn't really have a paying job for a long time. So I had to move in back in with my parents in New Jersey.

Chris Erwin:

Yeah. I really like how you described that you had to be foolishly confident. I think when you do the math, the odds are totally stacked against you in starting a company. So you have to be delusional in a way and saying like, "I can do this." And so whether that's just like in your blood or in your nature, or at your point, you just didn't even know any better.

Adam Sachs:

No, I just didn't know any better.

Chris Erwin:

That's an asset.

Adam Sachs:

Exactly. I think it was truly in my ignorance helped in that way, because I just didn't know any better.

Chris Erwin:

I think I remember. So you used to host at your father's house in Little Silver, used to host a lot of basketball games. You play a lot of like three on three or five on five, what have you. I think we were over there one day and I think I had heard rumors that you're like, "Adam's starting this company and now he's applied to Techstars and he's getting into this program."

Chris Erwin:

And I was like, "Adam, I don't understand what you're doing. I'm confused. What is this?" Startups we're in cool yet. But you had a mission, you had a plan. And so then you applied to Techstars. What was that application process like?

Adam Sachs:

We realized that we had to raise money in order to build this thing. And so we ended up meeting through friends of friends some early stage VCs. They were rightfully for the most part, like, "You guys are not really investible at this point. You don't really know what you're doing." And we hadn't really built much at that point. But one of the VCs who really, I think believed in us was this guy, Jason Mendelson, and his partner, Seth Levine at the Foundry Group in Boulder.

Adam Sachs:

And we got connected with them and they were also like, "You guys are onto something here, but you're in New York, we're in Boulder." But I think they really liked us and believed in us. And so they encouraged us to apply to Techstars. And we had never heard of Techstars before, but they're intimately involved in starting Techstars and supporting Techstars.

Adam Sachs:

It was not an obvious thing for us to do because I had never heard of it. I didn't know what a incubator or accelerator was at that point. Again, this is a different time where now there's a million accelerators.

Chris Erwin:

That's great. And this was literally 12 years ago. So it's not we're talking about 35 years ago. This was like within generally past decade.

Adam Sachs:

Not that long ago, but it was a different world. And so yeah, we applied and I think through the help of those guys, we ended up getting in. But even then I think, again, points to our kind of foolish ignorance, we were like, maybe we're a little too far along for this Techstars thing is what we thought. We were like, we have some users on in our Facebook app. That's how we started.

Chris Erwin:

Okay. It's just also funny to hear, like this speaks to the delusional part of actually we're pretty advanced, like we have users, so we actually really needed to be a part of this program. Maybe we should just skip this. That's what you guys wanted.

Adam Sachs:

Again, pretty dumb, but it was really, really valuable experience. It's a mentorship driven experience. We needed mentorship. I studied history and film in college. Dan, I think studied communication or something. We didn't really know what we know. And also there's really not a great curriculum probably even to this day for starting a company. In my opinion, you have to talk to people who have done it. Learn from people who have done it.

Adam Sachs:

I think it's not something that you graduate, even if you, I know very few schools have an entrepreneurship program, but I think even if you graduated with a degree in entrepreneurship, you still don't really know what you're doing until you get in there and start doing it.

Chris Erwin:

Yeah. So you're at Techstars, clearly it was a positive experience. You graduate.

Adam Sachs:

Yes.

Chris Erwin:

And then did you raise money immediately upon graduation at demo day?

Adam Sachs:

Yeah, immediately. We had a really good presentation actually. We were working with our mentors and again, these guys, Jason and Seth at Foundry Group became our mentors. And the second half really of Techstars is like for preparing, at least at this point. It might've changed. Again, this is 2008, so this is a long time ago. But at that point, the first half is a lot of mentorship. The second half is really like preparing for demo day.

Adam Sachs:

And I remember we put together a presentation, a draft representation. We brought it over to Jason in his office and sat down with him and walked him through it. And he was just like, "Yeah, it's pretty good. I don't know. It's fine. But it's missing you guys," is what he said. And I think he'd gotten to know us and know our personalities or whatever. And we went back and I remember we locked ourselves in a room with our small team of four of us for like a weekend and came back to him on Monday. And it was a funny presentation. It was like a comedy driven presentation and he was just like, "This is it, this is it."

Chris Erwin:

Actually I never thought about that. But thinking about your roots in comedy, entertainment, improv, and then writing with Ally at Northwestern, pitching to investor is about telling an incredible story of excitement, why we are the best team to do this, really peaking their interests. And I was like, you have like the formula for that. And I guess that's what this guy wanted. And then he didn't know what you had in you. And you're like, "No, let us show you."

Adam Sachs:

Yeah. So the presentation went great. And I think for a lot of people, did a lot of the VC side of it. There's 300 VCs in the audience or something like that. I think for a lot of them, it was the first time they saw like an actual funny VC pitch or whatever, like startup pitch. And I don't think it was necessarily like the humor that attracted ... Any smart VC is not going to be like, "I'm going to invest in the funniest entrepreneur."

Adam Sachs:

On the surface, it was funny. But when you got beneath it, it was like, "These guys actually know, they have a good handle on what their vision for the business is." So yeah, we did raise money immediately.

Chris Erwin:

An interesting highlight from that point though, is I think when investors see for an early stage company is okay, do they have a product? Have they built something? Are they solving a real problem? But it's so early. Even if they have a little bit of users is likely pre-revenue. So there's just an incredible amount of risk. So they're really betting on the founders, on the ability of the founders to attract future capital, tell a good story, recruit a team, and build a team and motivate people.

Chris Erwin:

And so what they could have seen in you is like, "Okay, there's this magnetism of this team that's going to be able to attract people to their team and get them excited about this ridiculous mission that they're on." So it seems like you have this asset of your storytelling, was actually like checking a major box for these investors. If you think about it that way.

Adam Sachs:

Yeah. Maybe. We also rushed the fundraising because this was like August, September of 2008, and the financial world was starting to just collapse around us. And so, once we saw that happening, we were pushing our investors to like, get your checks and get your checks. Because that we knew that very shortly after that, we could feel like the economy was collapsing.

Chris Erwin:

Got it. So money comes in the bank. And how much did you raised initially?

Adam Sachs:

So funny. Again, only 12 years ago, but we raised a series A and it was like a $1.2 million, which today is like a pre seed amount of money. But at that point, that was our series A.

Chris Erwin:

Okay. And that was on top of a little bit of family and friends money that you raised.

Adam Sachs:

Yeah.

Chris Erwin:

Got it. So you have the money, your team is feeling excited. You move to New York City. I remember that you had offices in Union Square. I don't know if you moved immediately there.

Adam Sachs:

Yeah, we did.

Chris Erwin:

I was part of a beta test for a group date in the lower Eastside.

Adam Sachs:

I think like a Max Fish or something.

Chris Erwin:

Yeah. There's like six or seven guys. Six or seven girls. We're all competing and say who's getting them like the most amount of face time with the other side. It was a really funny experience. There was also a launch party that was associated with it.

Adam Sachs:

Yeah. At Barna, which no longer is on Park Avenue South.

Chris Erwin:

So I remember I was like, okay, I don't know what Adam's doing, but if I get invited to cool parties and get to go on like group dates and maybe meet women, I'll be supportive. All right. So tangent. You're in New York City, you have the company, and now you're there for the next six years. What do you remember as a major inflection point after raising that money and saying, "Okay, now we're scaling this company." What were some of those key milestones?

Adam Sachs:

One of them, the biggest one for sure is we were out there hustling having parties. We would literally like throw a party at a bar in the East Village, bring our digital cameras because that's how you took pictures then and computers and buy people drinks to like sign them up in exchange for having them have a profile on our site. So we'd be like, "Hey, do you want to try our site? We'll buy you a drink."

Adam Sachs:

And so, we would then take their picture at the bar and make a profile for them. Because it was a grind to get people to sign up.

Chris Erwin:

Were most people amenable to that? Or were some people turned off?

Adam Sachs:

Half and half I think. We had like maybe dozens of people signing up every day in New York, but we'd go home at night and look at our Google analytics and be like, "Hundreds of people signed up today in India." Or like thousands of people signed up today in India at one point. And so that was sort of the inflection point, which is like, we're pushing too hard for something that maybe there's not as much of a demand for here as there is for other places.

Adam Sachs:

And so at that point it was like, let's understand this, what is going on here? We didn't understand India or some of the other markets where we were seeing this natural, organic demand, and India was one of them, for sure. Also like Singapore and Malaysia and Indonesia and other Asian countries. And at that point, it was like, that was a huge inflection point. And it was let's understand what's going on here so that we can decide, is this worth pursuing.

Chris Erwin:

We're back from a quick break and maybe unbeknownst to Adam, but I just actually we have a bunch of our high school friends on group text, and I just sent a crowdsource message of any questions that we should ask Adam on the podcast. So I might check this at the end when we get to the rapid fire, that has been seated within the group.

Adam Sachs:

Awesome.

Chris Erwin:

So we'll see what happens.

Adam Sachs:

Our friends are deviance. I don't want to see what their questions are.

Chris Erwin:

So we were just talking about you're now in New York City with funding, you're scaling Ignighter. You're hustling, you're grinding, you're going out to the bars, you're signing up people like on location. So then what you're just touching on, which is interesting is this theme of the unexpected. So you're building this business, you're looking at your metrics, and all of a sudden you're seeing user growth in India and in Singapore and these Asian countries, that's not what you're necessarily intending for, but it's happening.

Chris Erwin:

So as you start seeing this information, there's certain types of leaders and people that would say, "That's that's interesting, but we're not going to do something about it." What was the point where you're like, "This is meaningful. And now we're actually going to pursue this. This is opportunity." What was that decision making process?

Adam Sachs:

At first, it was like, this is interesting, but it's not our mission. So we ignored it. For I don't know how long, for maybe a few months. And then eventually it was like the discrepancy between how hard we were hustling and grinding to sign up users one at a time in New York versus literally I think at our peak, there were like 5,000 people a day signing up in India. And it was like, "What are we doing here? Let's figure this out. What is it that's making it click there?"

Adam Sachs:

And that's when we started to talk to people who knew the market way better than we did, talk to people who knew the culture better than we did.

Chris Erwin:

How do you do that? Who do you talk to? The same thing, like figuring out who do you talk to about Techstars? Did you call up your investors, did call friends?

Adam Sachs:

It was a little bit of both. Yeah. And we were able I think through our investors and through the Techstars network to meet people who are either entrepreneurs who were maybe of Indian descent and had family in India or who had family that were building companies in India. We actually shared an office with a company, coincidentally enough called exclusively.in. I don't know if they exist anymore, but they were a company that was building like fashion products in India.

Adam Sachs:

And they were really closely connected to the market. And so they started to like help us and connect us to angel investors in India and VCs in India. And those people help. Once we started to understand this, we went out and we raised more money from investors who were interested in that path in pursuing that in India story.

Chris Erwin:

Growth in Indian market.

Adam Sachs:

Yeah.

Chris Erwin:

Okay. And how much money did you raise at that point?

Adam Sachs:

I think maybe three or three and a half million, something like that.

Chris Erwin:

Okay. And at this point, are you feeling excited?

Adam Sachs:

Excited but scared too. We'd never even been there at that point. We still hadn't even been to India. It was hard enough I think building a company like in a market that we knew inside and out. And so the idea of building a company somewhere else felt like how's that going to work?

Chris Erwin:

I can understand the mix of emotions because maybe there was some frustration with the challenge in getting traction in the United States where you were focused. So this is in a way maybe a bit of a lifeline.

Adam Sachs:

It felt like a lifeline, but it also felt like we were riding blind a little bit too. Our first move was like, now that we know we have all the traction in India, let's put up a landing page so that only people in India see that shows people that look like they're in India and not people that look like they're in New York so that and you can kind of geo target in that way. But we didn't know the market well.

Adam Sachs:

So I remember our first landing page in India we're like, here, these are two beautiful looking Indian people. Let's put them on the landing page. And it turned out, we put a picture of like a bride, like a woman wearing a bride's outfit. And we were trying to be like the antithesis of like one of those like serious like marriage dating sites. And it was like literally a woman in bride garb.

Adam Sachs:

And then one of our investors who I guess knew the market was like, "What are you doing? That's not what you guys are."

Chris Erwin:

Not your brand.

Adam Sachs:

Yeah. That's so off brand. So it took us a while to figure it out.

Chris Erwin:

This all leads to a point where you end up moving to India.

Adam Sachs:

Yeah.

Chris Erwin:

And you moved there with your wife, Molly.

Adam Sachs:

Sort of. We had an apartment in New York where we lived and then I got a place in India and mostly it was me going over there. Molly did go. But it was mostly me going by myself.

Chris Erwin:

Is there one memorable moment of like you're in India and you're just in shock being like, "Wow, this is just feels so different."

Adam Sachs:

I think just in general, just the business norms were really hard. Like when we wanted to start processing payments, for example, I remember we had to get some kind of certification from like the Royal Bank of India or something like that. And then that took forever and we had to be compliant in a certain way that I didn't really understand. And at one point I was really an expert in all this stuff.

Adam Sachs:

And I've fortunately since forgotten, I think most of it. But it was like very hard. And then also people didn't really have credit cards or a lot of people didn't have credit cards. And so you have to figure out other ways to pay. And there were people that were paying with their mobile phone credits and it was very, very different and in that way, challenging.

Chris Erwin:

Got it. So then you eventually sale to Barry Diller's IAC. How did that come to be?

Adam Sachs:

Well, to be honest, and this is something that they don't really tell you when you start a dating site is that there's not that many buyers out there for dating sites. There's one universal behemoth in the dating world that wants to be the globally dominant business and that's IAC. So a typical sales process would have competitive nature attached to it where there's like a bunch of different companies bidding for your business.

Adam Sachs:

It was hard for us to drum up a competitive process when there's like really just one buyer out there.

Chris Erwin:

So you sell to IAC. And then at that point, I think that was a big milestone because you started a company, you ran it, build and scale the team, transitioned to an international market, and then you exited it. And I don't believe this was like a major liquidity event for you, but it was a sale. And that is a big stamp of approval. And so now it's kind of like you have this big entrepreneur stamp on your back.

Chris Erwin:

And so next, I think that you ended up going to Midroll Media, and this is another major inflection point in your career where you kind of lay the foundation for becoming this early and seasoned audio executive. And this now like fast growing industry. And what sold you on going into podcasts and audio and then moving to LA?

Adam Sachs:

First of all, all my time spent on planes going back and forth from New York to Mumbai and then being in Mumbai by myself, I had become obsessed with podcasts. I was listening to them all the time. They were my companion in India, basically. And as we have already established, always wanted a career in media. I've joked, like I've studied radio, TV, film. I never thought I would be doing something in the radio piece of it, or the RTVS, because that wasn't even really part of the curriculum.

Adam Sachs:

But I became obsessed with podcasts. I met a guy named Jeff Alrich who started Earwolf. And in fact, Ally Hord introduced us. And I met him when I was still at Ignighter or step out. And we just met us to like CEOs kind of commiserating as startup CEOs often do about like the various challenges. But I really loved his business. Even though it was still small at that point, it was bootstrapped.

Adam Sachs:

So he didn't have investors and it was profitable and it was growing and it was in an area of media that I loved and that I felt like was just kind of getting started. So yeah, we got to know each other. And then the timing worked out that after we sold to IAC, he reached out saying like, "I'm looking for someone to help me build this business, like a COO type. Do you have anyone in mind?"

Adam Sachs:

And I throw my hat in the ring. And then also the other piece of it was that we, at this point, had like a baby in New York City and we were feeling kind of done with New York. It was hard to have a kid in New York. I think the suburbs didn't really appeal to us. As I mentioned, LA always had some certain draw. We didn't necessarily know that we wanted to leave New York and go to LA, but this just felt like the right opportunity to try it.

Chris Erwin:

It's interesting. It feels like it's checking a few boxes for you. Because I know in talking to you at that time, I think you had a really great experience at Ignighter. You learned a lot, you've built a great investor network, but it was challenging. You had with investors, a lot of different stakeholders in your business, different points of view, weren't profitable and sustainable and a lot of the stage of the company.

Chris Erwin:

So Adam, you have a really exciting run at Midroll before you exit a couple of years later. You joined as COO and then in just nine months, you're promoted to CEO. So tell us about that journey. And what did you first focus on when you joined the team?

Adam Sachs:

It was a lot, we were building this new network called Midroll. The business started as Earwolf and that was continuing to grow, but the new-

Chris Erwin:

Earwolf was a network of comedy podcasts.

Adam Sachs:

Correct. Yeah. But the new thing that we were building, which we saw as our real growth opportunity was Midroll and Midroll is what connects podcasters to advertisers. They really hadn't been professionalized at that point in the industry. But as the industry was growing, it was like more and more podcasters wanted to make money, obviously.

Adam Sachs:

And advertisers were starting to realize that podcast listeners are passionate and they develop this intimate relationship with the podcaster. And so podcast ads could be very powerful in that way. And so that's where we saw a really big opportunity and started to invest a lot. It grew very quickly.

Chris Erwin:

It's interesting to hear the timing of that because it reminds me when I was at Big Frame, which was, we were creating short form, social content online and managing digitally native creators, people that were on ... YouTubers, people that were on Facebook, on Instagram, et cetera. And a big part of our growing business was connecting marketers and advertisers with our talent.

Chris Erwin:

And so that's a very similar dynamic to what was happening with you. Okay. So you're leaning into that. And then did you know that within like nine months that the CEO is in my orbit or it's going to happen or it was kind of just bestored upon you?

Adam Sachs:

No. That wasn't the case. We were growing quickly trying to add people quickly. The business started in a very ... it's credits Jeff, but in a very scrappy way adding more people and elevating the early people who had really done a great job. And I honestly think that the business got to a point where it was ready to go to a different level. There was a scrappy level.

Adam Sachs:

And I think once it was ready to go to that growth level, Jeff kind of felt like it was better handled if I were in the day to day of it all, and we didn't have a board, which was great. And another thing that really appealed to me and so like Jeff and I were the board, basically.

Chris Erwin:

Make fast decisions.

Adam Sachs:

We were able to make really fast decisions. And so, he was still involved in the business, but not really in the day to day.

Chris Erwin:

I just want to quickly pause here. I think there's a good takeaway for our listeners that explains your rapid rise at Midroll. So I've worked with you and known you for many years, and you've also developed an industry reputation with many others that you're very clear thinker and strategist, and that you have a point of view on market opportunity. You do a quick pros cons analysis, and then you make a swift decision to move forward.

Chris Erwin:

And then on top of that, you also have this great magnetism that allows you to build teams and rally smart people around you. I believe that this has caused success throughout your career and is really powering your growth now at Team Coco, which we'll get into in a little bit. So I just wanted to call that out quickly.

Adam Sachs:

I appreciate it.

Chris Erwin:

So now you're CEO and as we've talked about, because I was a COO at my last company and we used to joke that COO is like, you have a lot of responsibility. You're essentially running the company, running the team, but the buck doesn't stop with you. Like if there's a really tough decision to make like, that's the CEO or that's the founder. Like that's not me, that's them. So you get to be like everyone's best friend.

Adam Sachs:

Yeah. COO is secretly like the best job in the world.

Chris Erwin:

100%. So now that changes for you, now you're the CEO, the big decisions really fall on you. How did that transition feel?

Adam Sachs:

A little bit scary. And honestly, one of the reasons it was scary and I had experienced being a CEO because I was CEO of Ignighter. So I knew what it entailed, but one of the things that was a little bit scary about it was actually that we had so much momentum. We didn't make this transition because things weren't working and we needed to try something new, that wasn't really the impetus at all. It was really about growth and that almost put more pressure on me.

Adam Sachs:

It was like, don't fuck this up because we have a good thing going and we're growing quickly. So, that part felt scary. It was also challenging to be a part of the management team. If you think there's like the CEO and then below the CEO, there's like three or four C level executives. It was a little bit challenging at first or scary at first to be one of those three or four people on the management team who then became the CEO and had to manage the people who were my peers or on that same level as me.

Adam Sachs:

So that part is always intimidating at first. I think it certainly didn't come without any growing pains that would never happen, but it worked, it worked.

Chris Erwin:

That's a very interesting call out. When you started Ignighter and essentially it's nothing, so there's like nothing to lose. It's like you're at zero and there's all this upside potential and you're like, "All right, let's see where we can take it." But now, you go to this company that was founded by someone else that has some real momentum and traction and the rains are given over to you.

Chris Erwin:

That's a totally different responsibility set or feeling. Clearly great experience. So now you're the CEO and it's funny at this time, this is also people were calling this is Peak Podcast. This I think is around 2014. And so I think there's a chance for a liquidity event. There's a chance to sell the company. What was the impetus for that sale?

Adam Sachs:

It was a couple of things. It was the first thing that you said, which is like podcasting was having a moment. Serial came out and Gimlet launched and suddenly a bunch of media companies were saying like, "We have to figure out what's our podcast strategy?" And so we started to get a lot of inbound interest from both investors and potential acquirers and having, like you said, we've been so excited about not having investors and we were profitable and growing quickly.

Adam Sachs:

Personally, I didn't want to bring on investors. And I think that the team agreed. We didn't need it. So why bring in other people to just start having their own kind of agendas? But we did feel like if there was the right buyer, it should be something worth pursuing, at least having the conversations. It was like, because we were bootstrapped was owned by a few of us, the business.

Adam Sachs:

So, we could have a meaningful outcome potentially without the number having to be astronomical. And so, we thought who knows, maybe this is just the first wave and it goes away forever. And so, we didn't want to miss out on podcastings moment if something new came along. And then the other piece of it is that there was money flowing into the space competitively.

Adam Sachs:

And so it was like if we were determined to stay bootstrapped and we didn't want to raise money while people around us were raising money and what does that mean from a competitive landscape? So, that was like all the things we were thinking about at that time.

Chris Erwin:

It was a beautiful moment to sell. And I think the timing was great. And I remember when I was at Big Frame, this is just after we had sold the Awesomeness TV and I was in the offices at our offices at Burundian Olympic. I remember you calling me like late night, like six or 6:30 PM. And we spoke for like an hour, hour and a half of like the pros and cons of a sale. And how do you manage a sale process?

Chris Erwin:

Because there was a lot that you were thinking through and I could tell that this was a big decision you were taking very seriously and that you are excited, but also scared at the same time.

Adam Sachs:

That's totally true. I guess as they're six month process of going around and pitching the company.

Chris Erwin:

Yeah. Which can be brutal because the moments are, this is great. We're headed in a great direction, but this could also fall apart at any moment. There's an investor that's excited, but then in the middle of doing diligence, maybe it all goes away and we miss our moments.

Adam Sachs:

Yeah. Exactly.

Chris Erwin:

[crosstalk 00:37:11] on edge the whole time.

Adam Sachs:

For sure. And I think we were worried that if that were to happen, we did have such great business momentum, if that were to happen, would that kill our business momentum, would that kill everything? It felt a little risky at the time.

Chris Erwin:

Unique moment that happened where I think as you are talking to different prospective buyers, you had a conversation with Andy Redmond who was the president of Tornante and who we also knew who went through our high school year above us. And that there was a unique moment that happened at Spargo. Tell us that quick story.

Adam Sachs:

So Andy Redmond is the president of Tornante. Tornante is Michael Eisner, former Disney CEO, it's Michael Eisner's vehicle for investing and acquiring companies. And when I came out to LA, I reached out to Andy and we hadn't stayed in touch really. Our families kind of know each other. We knew each other a little bit growing up, but we hadn't really stayed in touch. But I just reached out to him because I thought he had such a cool job.

Adam Sachs:

Tornante acquires media companies and invest in media companies. They make content. They make really great stuff. They make BoJack Horseman, for example. They do that. And then they also like just bought a English premier league soccer team. So they do all this and, it all kind of rolls up to Andy. So I thought Andy had such a cool job. And so we met or we had lunch early on when I was out here and he immediately, I think, got interested in what we were doing, and we stayed in touch.

Adam Sachs:

And then during the sell process, we communicated and he started to get excited and brought us in for several meetings. And then one of them was a lunch at Spargo with Michael Eisner. I told you the story because it was one of my very just surreal, most surreal, I guess-

Chris Erwin:

LA, Hollywood.

Adam Sachs:

Exactly, where I was like at a table with Michael Eisner who by the way is from Red Bank. I don't know if you know that. His whole family's from there. So we had this whole conversation with Andy about we all grew up in the same area and-

Chris Erwin:

Improv jam.

Adam Sachs:

He was one of the funniest at improv jam. His guessing was incredible. And so we had this whole conversation and he was really excited about what we were doing. And at one point during the meal, Wolfgang puck came over and sat down with us at the table and started giving Michael Eisner a hard time in a playful way about building a house too big that it was obscuring his view and-

Chris Erwin:

You're just like, what is happening?

Adam Sachs:

Yeah. And then literally Sidney Poitier's at the next table. And that was all like catalyzed by Andy. It was a very funny thing because we grew up in this very small town that seemingly very disconnected from all things Hollywood and literally geographically, like on the other side of the country.

Chris Erwin:

There must be something in the water in Monmouth County. That's a really funny story. So you end up selling the company to E.W. Scripps. You end up going over there and helping the company transition for a bit over a year. At that point you had, we were talking about like you had the entrepreneurial stamp on your back from Ignighter, and now you have in the sale of Midroll to E.W. Scripps.

Chris Erwin:

You have a stamp on your back as you are a legitimate audio executive. Podcasting an audio, digital audio is a fast growing industry. And Adam is a leader that has incredible relationships, has built an incredible portfolio of audio content. While at Earwolf, you also were able to help build out the ad sales arm and build out this scalable profitable business with a successful sale and exit.

Chris Erwin:

So you have this brand as you're an audio executive. And I think that's really exciting. It's really great. I'm also curious to ask, I don't know if anyone has asked you this, is that the brain that you wanted one, and then two, do you feel that that could also pigeon hole you a bit where it's like, okay, I'm on this path, but maybe my career ambitions are a bit broader in entrepreneurship or in other areas of entertainment? What do you think about that?

Adam Sachs:

It's a good questions. I am sure I'm pigeonholed in some ways. I'm sure people look at me for better or worse as an audio guy. I think a couple of things. One is, I do think there are a lot of things I've learned in building companies. And certainly, probably more specifically in building Midroll Stitcher that are applicable outside of just audio here at Team Coco, we're building a digital media business. Audio is a really important part of it.

Adam Sachs:

But there are things I learned through that process that I think are applicable. But I still believe in audio in a way that I think if I were pigeonholed into something that I thought that I wasn't super bullish on or that I thought was kind of lame, then it might be more of a bummer. But I think audio is cool. It sounds dumb. But I don't mind that that's like my brand, if it is my brand.

Adam Sachs:

And I think it's allowed me to meet a lot of cool entrepreneurs and work with a lot of cool companies. And I still think that the industry is in its early days. And so, I don't mind that being like part of or all of my brand.

Chris Erwin:

When people look at your career story, just even if just listening to this podcast, that it's very multifaceted. And then in entertainment, I agree, audio is not pigeonholing you because audio is a medium to express yourself and to create story, to share ideas, and to create IP. And that can manifest in a variety of ways, whether it's a TV, film, or a theme park, or short form social content, and you look at all the others in the same.

Chris Erwin:

And so I think it's actually a really fun, medium to play in right now because it allows you to experiment in a very low cost and rapid yet efficient way. And then if you want to go premium as well, like Conan Needs a Friend, one of the best performing comedy podcasts on the planet right now, there's so much that you can do, but just one aspect of a business.

Adam Sachs:

Yeah. I agree. I love audio. So, I don't mind it.

Chris Erwin:

Adam Sachs tagline, I love audio. Awesome. You sell Midroll to E.W. Scripps and I believe the price point was somewhere in the range of if there was like an earn out maybe 55 to 65 million-ish in that range. Adam is nodding. So I think I'm in the right ballpark. So after the sale, Adam has a lot of options. It's after Midroll, you then go do a stint as an entrepreneur residence at Chernin, the Chernin Group.

Chris Erwin:

You work with some brilliant minds like Jason Bergman and Mike Hearns and the rest of the Austin team over there. Steve [Cosnio 00:43:18] and I'm going to blank on a bunch of other names. You even start advising higher ground audio, the production arm of Barack and Michelle Obama. There's a lot of different things that you can do. And I think some of the options include, you could start your own company, start another company.

Chris Erwin:

Or you could go work for a team, and you actually end up working for Conan and Team Coco and overseeing his entire digital business. In that moment, how do you decide what you're going to do?

Adam Sachs:

The way you describe it makes it sound like I had a lot of opportunity, and I did. It's true, but it wasn't obvious to me what to do which is part of the reason I went to Chernin and I was just like, I don't have a ton of conviction around a business that I want to start. I know what it takes to build a business from the ground up. And there's nothing that I'm obsessed over right now that I just know I have to go do this.

Adam Sachs:

The idea of joining something that was early and interesting appealed to me. So my thinking was like, let me just go where there's really, really, really smart people. And to your point, the Chernin Group, especially as it relates to media, has some of the smartest. And so spending a year with them, first of all, learning how to be an investor, which I had zero experience doing, really appealed to me because I wanted to just understand that world a little more.

Adam Sachs:

Meeting really smart both investors and entrepreneurs on the media side or in the media world was really appealing because I felt like it would help me just figure out what to do next. And with the Conan thing, and maybe it goes back to this theme of not overthinking it, but it was this opportunity of you can work with arguably the funniest person on the planet who has a reputation for also being a good guy and a team that really is filled with good people and that like each other, and that have been around here for many, many, many years as he explores.

Adam Sachs:

And they all explore launching something new, but with the added benefit of brand and this talent and this reach that's all here, it was kind of like, let me just see what happens. And as we've already established here, comedy's very important to me. And there was talk of maybe starting a podcast network and that was appealing to me for obvious reasons. So yeah, it literally just checked a lot of boxes.

Chris Erwin:

How were you first introduced to Conan and Team Coco?

Adam Sachs:

Through Chernin. It was like, there was a connection between some of the people that turned in and some of the people at Team Coco. And that's how I got to know them. And I did a little bit of consulting work to help think through this business plan, because what it is is Team Coco has existed since 2010, Will keep me honest, 2010. Yes. But it wasn't until a year and a half ago that there was this pivot into building it into a full on media business.

Adam Sachs:

It existed as a really successful marketing arm that marketed digitally the TV show, the linear show. And that became its own business in a way. The marketing of that, the distribution of those digital clips from the TV show and monetizing them across YouTube and social channels became a business. And then that ultimately became the foundation for what Team Coco is today.

Chris Erwin:

Just to be clear for the audience, the tent pole format that Conan has is his talk show with TBS.

Adam Sachs:

Correct.

Chris Erwin:

Got it. So you're like, okay, this is an amazing marketing arm, but you also had a point of view of like there's a lot more to do with this.

Adam Sachs:

Yeah. And a lot of that came from my experience at Midroll center, but the year I spent at Chernin, meeting a lot of what I thought were some of the best and most forward thinking media companies.

Chris Erwin:

And onboarding into Team Coco, it seems that one of your first early projects was getting Conan podcast network off the ground. Is that accurate?

Adam Sachs:

Yeah, that's true. They had tried a couple, maybe like pilots of a podcast. There was talk of doing a podcast. Conan was half interested, but pretty skeptical.

Chris Erwin:

On his podcast, Conan Needs a Friend sometimes he'll make references to you as the executive producer. He's like, "Yeah. I don't know what this podcast thing is. Is this even real? Supposedly we have downloads. I still don't know if there's money coming from it. I don't see it."

Adam Sachs:

Yeah. I think now he finally gets it, but yeah, for a while even after it launched and was successful, he was still like, is this thing real? I don't know. Am I sitting alone in this room talking into a microphone and no one's hearing it? But what's happened is now he gets stopped everywhere he goes, and people tell him, "I love the podcast." So he knows it's real. Or it's like some massive Truman Show scam where everyone is just faking it and coming up to him. But yeah, no, he knows it's real at this point, which is good.

Chris Erwin:

He has one of the best performing shows. That's probably important. I want to just jump back for a quick sec. Was it hard to get the teams buying or when you were getting recruited, was it like, "Look, this is what I want to do here. I want to build out a podcast network." And so when they brought you on, it was like, "All right, we know what Adam's plan is. So if we actually bring him on a COO, we're going to get things done." Or was it like an uphill battle?

Adam Sachs:

We put together a business plan that included a variety of verticals, audio being one of them. It was like the digital distribution business, which is the core business. It was live events, it was podcasts. It was stand up specials. And that was part of the whole business plan that I helped put together. And there was buying on the business plan holistically for sure.

Adam Sachs:

I think what we've seen over the past year is that audio has become a major investment area for us. And it helps that Conan's podcast has done so well.

Chris Erwin:

Yeah. Maybe you can also reference this like, look, if Obama is leaning into this, there's something.

Adam Sachs:

Exactly. Now that Conan is one of many A-listers or a plus listers, like the Obamas who are understanding this is a huge opportunity.

Chris Erwin:

So now you launched Conan Needs a Friend and there's a few other formats as well that you guys have launched. Remind me.

Adam Sachs:

Yeah, we have several podcasts. We have Conan O'Brien Needs a Friend. We have the three questions with Andy Richter, Inside Conan, and Important Hollywood Podcast are all unscripted podcasts that we've launched. We've launched two scripted series so far as well, one called Frontier Tween and one called Smarter. And those are scripted narrative, audio podcasts.

Chris Erwin:

And are those exclusively on the Luminary platforms?

Adam Sachs:

Those are exclusively on Luminary. Exactly.

Chris Erwin:

Got it. Thinking about 2020, how do you want to build out the audio initiative for Team Coco? Where do you guys see as more opportunity?

Adam Sachs:

We want to continue doing both scripted and non-scripted. So far, all of our unscripted podcasts have been hosted by people literally within this building, Conan and Andy Richter and Mike Sweeney and Jessie Gaskell who are both writers on the Conan Show. And so for us, and this is like a broader theme just for us to be successful as a business, we have to expand our talent network, both in podcasts and in the digital video that we develop and in the live shows.

Adam Sachs:

Everything, it can't rely as much as you have a huge competitive advantage when you have Conan being the center of a podcast. Because not only is he so famous, but he's so talented, but there's only so much scale you can get out of that. There's only so much you can squeeze out before he just like collapses or revolts.

Chris Erwin:

If he's listening to this, just like, "Adam's going to like squeeze more energy and time."

Adam Sachs:

He and I talk about it a lot. He talks about it a lot. He knows that we push him really far and it has an incredible amount of endurance more than most people. He does more than most people at that level, but there's only so far he can go. And so in order to be successful, we have to do more with other people. That's a big theme for us.

Chris Erwin:

Well, it's interesting to hear about the endurance. Because I think I was listening to a podcast with him and Jimmy Kimmel, where he was just talking about how hard they work. They're taping a show every day, their talk show. And then just all the other content that they're creating a short form format for socials, for marketing, for their podcast. It's just a lot of work.

Chris Erwin:

So it's not like nine to five, Monday through Friday. It's like they're on all weekend working and prepping and writing and all of that.

Adam Sachs:

Yeah. He works really hard.

Chris Erwin:

Along with a great team behind him that works really hard too. Okay. Last question on Team Coco before we get into the rapid fire round and then also maybe do some crowdsource questions from our high school friends, TBD. Does any other things about Team Coco that you're excited about in 2020?

Adam Sachs:

I think building upon the things we've already started is important for us, like doing more live events, building on our podcast network, doing specials. We're making comedy specials for HBO Max, and hopefully we'll be making more content for other platforms. All that is I think exciting. We also are doing a podcast exclusively on Stitcher premium podcast called The Best of Conan Standup.

Adam Sachs:

Where we're taking five standup sets from every year dating back to the first year that Conan was on TV each year and highlighting those. So you can listen to ... it's hosted by Laurie Kilmartin also here within our walls. She's a writer on Conan and a great standup herself. That show is every episode is a different season of stand ups from Conan. Think there's like opportunity for us in gaming potentially. I don't know. We're trying to expand.

Chris Erwin:

Awesome. I think you guys have an incredible path forward. We are massive supporters of your business as you know.

Adam Sachs:

You guys are really helpful.

Chris Erwin:

To close out the Team Coco narrative. I think one of the things that Adam brought up in the first part of the conversation was just what attracted him to Conan was his sensibility that he's some amazing talented comedy writer who's silly and funny and smart. But it also like Conan is a good person. He's got good values and he's built out a team that he really looks out for, that he really respects.

Chris Erwin:

And he's really set the tone at the organization. And I can say, I was fortunate enough to get invited to the Team Coco and Conan holiday party at Yamashiro in Hollywood. And it's funny as I spoke to Adam and then as I spoke to some of his peers, like Willy Nevara, I don't know if I'm pronouncing that right. Steve Breslow and some of your other business affairs executives, they all said, "Conan sets us really special tone from the top."

Adam Sachs:

He does.

Chris Erwin:

I was there with a friend of mine, Maya, and we felt that in the room, it just like we've gone to a lot of Hollywood parties and I don't get excited by most of them, but this one was like, it felt different. Everyone was so open and it was a really good vibe. And I think that really leads to a really compelling and special creative environment working environment.

Chris Erwin:

And what I also heard from talking to one of the final executives there was that Adam is also a big part of setting that tone with the leadership. She made it very clear that that tone comes down from Conan, but it is also very much embodied in Adam and how he runs the Team Coco organization.

Adam Sachs:

That's nice. It's Conan and Jeff Ross, for sure. They really take care of their people.

Chris Erwin:

All right. Before we get into the rapid fire, I'm just going to check the text thread. Joe Venti asks, is this the rebirth of Ask Adam? Ask him to rewrite what dreams may come?

Adam Sachs:

The Ask Adam was my column in the Tower Tribune in the high school.

Chris Erwin:

Got it. Okay. I think that's the one that we'll take away from this. We need to go into the other ones. All right. So rapid fire, Adam, these are questions that you could answer very quickly in a few amount of words, one or two sentences or less. Here we go. Proudest moment slash accomplishment of your career.

Adam Sachs:

Conan's Podcast. I'm really proud of it's reached so many people, it's brought joy to a lot of people. It's brought a lot of joy to Conan who says that he feels really fulfilled by it and it's become, I think, an important part of his, I don't want to speak for him, but I think he said stuff like this. When he looks back on what he's accomplished in his career, I know that this will be one of the more important, special things that he's done.

Adam Sachs:

And I think it's really good quality. I think it's a really great show and it's because of Conan and Sona and Matt and I'm proud of it.

Chris Erwin:

Awesome. What do you want to do less and more of in 2020?

Adam Sachs:

I am always pushing myself to think bigger and to do more bigger thinking and to do less in the weeds of micromanaging. I think I just have like a tendency to do that a little bit and it's not a great quality. And so, I think getting more balanced in that sense I think is something that's important.

Chris Erwin:

Entrepreneurial advice. What one to two personal characteristics primarily drive your success?

Adam Sachs:

I think getting shit done. I think a lot of entrepreneurs sit around saying that they want to do something or that they should do something. And I think that the ones who see success are determined to just get something done and also stick around. I think it takes a long time for a company to find success. And it's not always fun, but I think hanging in there is important.

Chris Erwin:

And a quick side anecdote, we talked about this yesterday, but also you are not petty. You're not political. And even you were telling a story about your wife, who's like, "Adam, I hear that you're taking a meeting with this man or woman. Don't you remember a few months ago that you had like a really bad encounter?" You're like, "I don't remember that."

Adam Sachs:

I think I have a bad memory. I think maybe it benefits me sometimes, but I'm not good at holding grudges because I literally forget if somebody wronged me. And Molly who was my biggest defender is always does like stick up for me and look out for me. And she's like, "What are you doing? We hate that person. Remember?" And I'm like, "Oh yeah. Oh yeah, that's right. I forgot. We hate that person."

Chris Erwin:

Last three, advice for media professionals going into 2020. Quick words of wisdom.

Adam Sachs:

Follow the money is one of them. I think a lot of media companies in the digital space have come and gone because deficit financing, digital video in a way that isn't really sustainable anymore today. I think there's a lot of paywalls popping up, which I think is like in some ways a good thing, but in some ways a bad thing. Really understand what you're asking people to pay for, because I think media consumers are willing to pay, but only for certain things. If you're going to build a company in media, try to latch on to the best talent or the best content.

Chris Erwin:

Smart advice. All right. Last couple. Any future startup ambitions? See yourself starting another company in the near future?

Adam Sachs:

Probably not. I don't know. Maybe. A lot of it comes back to conviction. Again also I feel like I'm building a company right now and so that it's hard to even have the mind to even find the mind share or bandwidth to be like, "Well, what else do I want to build?" I do a little bit of advising and angel investing. And that helps me to scratch that itch certainly in not the same way, because being on the outside is not nearly the same. But if I got excited enough about something, maybe.

Chris Erwin:

All right. And lastly, people are going to listen to this and they're going to want to get in contact with you. What's the best way for them to reach out, develop a relationship?

Adam Sachs:

They can find me on Twitter @ARSachs. Yeah. Find me on Twitter.

Chris Erwin:

Find Adam On Twitter. All right, Adam. Thank you very much. This has been-

Adam Sachs:

Thank you. This is great.

Chris Erwin:

... absolutely [crosstalk 00:57:43].

Adam Sachs:

You're a natural. You're a good podcast.

Chris Erwin:

Thank you.

Adam Sachs:

I'm not surprised though.

Chris Erwin:

Thank you very. Much more to come. I look forward to our next conversation.

Adam Sachs:

Me too. Thanks Chris.

Chris Erwin:

The Come Up is written and hosted by me, Chris Erwin, and is a production of RockWater Industries. Please rate and review this show on Apple Podcasts and remember to subscribe wherever you listen to our show. And if you really dig us, feel free to forward The Come Up to a friend. You can sign up for our company newsletter at wearerockwater.com/newsletter. And you can follow us on Twitter @TCUpod. 

The Come Up is engineered by Daniel Tureck. Music is by Devon Bryant. Logo and branding is by Kevin Zazzali. And special thanks to Andrew Cohen and Sean Diep from the RockWater team.

Nicole Staple is the co-founder and CEO of Brideside. Nicole and her team reinvented the bridal shopping experience, and have raised more venture capital than any other female-led business out of Chicago. We discuss investor bias towards women, managing through rapid growth during her husband's cancer battle, and what rap lyrics have to do with ending meetings. Full episode transcript is below.

Subscribe to our newsletter. We explore the intersection of media, technology, and commerce: sign-up link

Learn more about our market research and executive advisory: RockWater website

Follow The Come Up on Twitter: @TCUpod

Email us: [email protected]

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EPISODE TRANSCRIPT

Chris Erwin:

Hi. I'm Chris Erwin. Welcome to The Come Up, a podcast that interviews entrepreneurs and leaders.

Nicole Staple:

I don't think they knew Sonali was pregnant and we never mention it. She was eight months pregnant. She was big. He came, he left and they told us they were passing because we were located in Chicago. You have to ask yourself is that really why they passed on the deal?

Chris Erwin:

This week's episode features my dear friend, Nicole Staple, the co-founder and CEO of Brideside. Brideside reinvented the bridal shopping experience, creating what they describe as an all-channel concierge service. And they've raised more venture capital than any other female-led business out of Chicago. That's super impressive. Yet Nicole, who I've known for nearly a decade, remains humble and is still very cautiously optimistic about her business. And just like when I knew her in business school, Nicole continues to work tirelessly to build Brideside.

Chris Erwin:

In our interview, you'll hear how Nicole always finds a way to overcome pretty big challenges like how she had to deal with investor bias towards women when first raising funding or leading Brideside through rapid growth during her husband's cancer battle. Despite all this, Nicole also knows how to add some fun into the mix like how her and her co-founder end meetings with rap lyrics. So I'm thrilled to bring you Nicole's story. It's such a good one. You'll hear wild stories and all along the way Nichole just exhibits such incredible courage and resolve. I have learned so much from her and she's a major inspiration for me. So this interview was an absolute delight. All right let's get into it.

Chris Erwin:

Quick heads up that my interview with Nicole was recorded back in February and prior to COVID. Yet her points about direct-to-consumer in 2020 are quite prescient, and Nicole's come-up story definitely stands the test of time. 

So Nicole, why don't we start out where'd you grow up, by the way. Remind me.

Nicole Staple:

That's a good question.

Chris Erwin:

I know you've told me, but I forget.

Nicole Staple:

A lot of different places. I was born in London. So my dad is British. My mom had moved to London and my dad followed her to get her PhD in economics from the London School of Economics. I was born there and my parents were also married there. Then my family moved to North Carolina to a small farm town outside of Durham and I lived there for the first 12 years of my life and then we moved to Princeton, New Jersey, which you know-

Chris Erwin:

Garden State.

Nicole Staple:

... because you're also from New Jersey.

Chris Erwin:

Much pride.

Nicole Staple:

And I went to middle school and high school in New Jersey and then my parents moved back to North Carolina. So now I'm sort of from nowhere. No one really lives in North Carolina anymore. My parents split. My family lives sort of all over. So I call Jackson Hole home now where my parents have a ski house and a place that I love.

Chris Erwin:

You have a pretty awesome geographical footprint in my opinion between Jackson Hole and Victor, Idaho and then Palm Springs where we went hiking a couple months ago. And then you also have an HQ in Chicago, and now you're based in New York City. You're all over and then I think you also-

Nicole Staple:

I'm a nomad.

Chris Erwin:

... spend time in North Carolina as well. So that's awesome.

Nicole Staple:

It's always feels a little freeing to be from nowhere, but it also can feel a little detached. I seriously don't know really where I would even call home now. So it's always been interesting to me.

Chris Erwin:

So I'm curious. Right now you are the co-founder and CEO of Brideside and we're going to help tell your story of how you got to where you are today. I'm curious, growing up, being born in London and then growing up in jersey and then you went to Lawrenceville and then to Wellesley College. What was your focus when you were at Wellesley. Why did you choose that school and what you focused on there?

Nicole Staple:

Wellesley was not a popular choice. It's an all-women's college outside of Boston. And no one in my class wanted to go there because it was all women. However, I had a lot of friends and school whose mothers had gone to Wellesley because it was maybe a bit more popular for that generation and I was particularly inspired by that actually and my mom and my grandmother are like amazing women and I really looked up to them and I thought like this was an opportunity to actually do something a little bit different. I actually think wanting to be different is something that's been a theme for me.

Chris Erwin:

Wanting to be different?

Nicole Staple:

Yes.

Chris Erwin:

Okay.

Nicole Staple:

I have this like fear of just living an ordinary life and blending in with everyone else and so I felt that it would be a unique experience, but I wasn't so sure I wanted to do it. Then I played lacrosse in college and so I was looking at schools where I could play sports and I knew I wanted to play division three. I got into some better lacrosse schools and then my dad told me he wouldn't pay for anywhere else that had a lower caliber of academics in Wellesley, and so the decision was sort of made.

Chris Erwin:

You said you have a fear of living an ordinary life. Where does that come from?

Nicole Staple:

So I think it's part of my DNA. I think it's like wanting things to feel exciting is very much a part of I think things I can't control and that's something I've learned over the years. But I grew up and my mom worked in public health internationally a lot and I had the great privilege of traveling with her to a lot of really interesting places. And my dad is a total adventure junkie and took us very rugged sort of backpacking and ski experiences growing up and I just think that really stuck with me. I actually believe it builds a lot of confidence to do that sort of stuff when you're younger and I think I've always sort of wanted to hold on to that because I think it was part of what like gave me confidence that I could do some of those things that other kids my age hadn't done or couldn't do.

Chris Erwin:

It's definitely a unique upbringing that you had between the adventures with your father and your mother in public health. So as you probably compared and contrasted your stories relative to peers of school, by just feeling of like, "Oh, mine's a bit different. Let's go with this. We got some momentum, and this feels right." Okay. So then you go to Wellesley where I think as you describe there's a lot of powerful women who had entrepreneurial ambitions or creating unique careers for themselves that, that really excited you and felt like that was part of this path and this vision that you had for your life. So while you're there, were there any entrepreneurial itches that you were scratching or was it, "Hey, I'm focused on a life on Wall Street," which we'll get into a little bit. What were you thinking there?

Nicole Staple:

No. I didn't really know. I was an economics major. I think part of that was again like what my parents did, but I think part of it was that, that made the world make sense to me I felt like when I was in my Econ 101 class, there was like an aha moment like, "Oh, okay. Got it. This is how the world worked and that just became my orientation." But certainly, there were things that were entrepreneurial in ways, but mostly like social justice oriented.

Nicole Staple:

Even when I was younger, I was really focused on the environment and conservation. So I would start little stupid organizations like sell baked goods at the farmers market to raise money for some conservation organization. Just little things.

Chris Erwin:

Yeah. Do what you can. Start local.

Nicole Staple:

Right, exactly. I was involved in some global health stuff in college in the same vein and worked with women in developing countries who were trying to get out of poverty. So that was sort of like where I was mostly focused and then investment banking became my path because that seemed to be what most econ majors did and it felt like a way to get training out of school and to make money, stand on my own two feet which both of those things, as you know, because you had a similar path, you can do when you do investment banking. But there was a very pivotal moment for me during my investment banking interviews where I met a very prolific entrepreneur and that very much changed my perspective of what I might want to do in the future.

Chris Erwin:

Oh, wow. Who was this prolific entrepreneur that you met?

Nicole Staple:

His name is Jeff Pulver he was the founder of Vonage. So he was the original inventor of voice over IP who ultimately became Skype.

Chris Erwin:

It's a pretty big industry.

Nicole Staple:

And as you know much more than that. So my girlfriend, actually a girl I didn't even know, but ultimately became a girlfriend at Wellesley and I were sitting next to each other on the Delta shuttle flight from Boston to New York for our investment banking interviews, and this guy sat next to us and asked us literally, "If you could do anything with your life, what would you do?" And we thought he was a little bit creepy. But we decided to entertain it.

Chris Erwin:

A little bit creepy.

Nicole Staple:

Then we ended up chatting with him and it was Jeff Pulver. As a result, both me and the woman sitting next to me actually talked about wanting to start companies one day and didn't really want to do investment banking, but we felt like we had to. We had a long conversation with him on the flight and ultimately we befriended each other and he ended up being in our lives actually for a good amount of time. Her and I ended up becoming pretty good friends and started working on some ideas at Wellesley together and that seed was sort of planted and ultimately led to me exploring that path later on.

Chris Erwin:

That is very interesting. I did not know that story at all. What did Jeff say on the plane that was like a catalyst or got you excited about entrepreneurship? And then my second question is clearly there was something inside you already and he was this spark that seemed to make it come to life. But what did he share that kind of got you thinking differently?

Nicole Staple:

I think it was more the questions he asked because when you're that age... And I don't know. I think it's different now. Starting companies is more of a thing. This was 2004, 2005. So it felt like something that was very isolated to Silicon Valley and I didn't even really know what Silicon Valley was. My dad was an entrepreneur and had started a few companies, but on the East Coast and it was a very different sort of situation.

Chris Erwin:

Not like today where there's HBO shows like literally called Silicon Valley.

Nicole Staple:

Exactly.

Chris Erwin:

And it's part of the media zeitgeist of everything.

Nicole Staple:

Yeah, I was totally clueless. So I think it was more really asking young people. Most young people I don't necessarily think get asked like what would you want to do if money were of no consequence, right?

Chris Erwin:

Yeah.

Nicole Staple:

You're really just thinking about how you get on your feet when you're that age. And so it was actually interesting to explore that. H was just very encouraging. He was very encouraging and positive about anything and ultimately this became like a longer-term relationship, but things that we would tell him he was just very enthusiastic about. I think when you are trying to put yourself out there just someone being encouraging of you can go a long way.

Chris Erwin:

I mean, this is me asserting some ideas, but maybe in your youth, when you're 2003, 2004 haven't even graduated college yet and someone is asking you questions and essentially they're thinking big. It seems like that was the impression that you got that Jeff was asking you some big questions, which is the assumption you're capable of a lot of things. And hearing that as a youth and then also as a woman probably at that time was maybe surprising. You weren't used to being thought of like that, particularly around your biggest ideas that maybe stray off the path.

Nicole Staple:

I mean, absolutely. And coming from Wellesley, our motto around campus is women who will. There were literally flags all across campus with the phrase women who will, women who will achieve, women who will change the world, women who will give back all over. We were very focused there on finding a path for ourselves and I think a lot of that looked like Hillary Clinton at the time, which was wearing a power suit and being in politics or finance.

Chris Erwin:

That was like kind of like the one image or female power definition that you had.

Nicole Staple:

Yes.

Chris Erwin:

Now, that's clearly changing a lot of ways and I think that you are helping to define what new vision is going forward.

Nicole Staple:

Yes. I've told myself if I am wearing a power suit in the future as I'm sitting here in like knee-high socks and a dress that I have done something wrong. So I think it looks different now.

Chris Erwin:

Yeah, I agree. Okay. So you're inspired from this conversation with Jeff. You want to understand how the world works, so that's why you like economics. Economically to investment banking and you commit to that path. So I think you did an internship at Goldman Sachs over summer and then afterwards you went to UBS. Was UBS the experience that you had hoped for. Was it what you expected?

Nicole Staple:

It was nothing like I expected. It was a wild ride. I ended up moving from equity research at Goldman to wanting to do investment banking and healthcare. UBS was a hot healthcare group at the time run by this sort of notorious banker who led a very interesting and intense culture.

Chris Erwin:

A lot is caught up in that definition. Interesting.

Nicole Staple:

Would not have flown in the era of MeToo. But at the end of the day when you have a coach that is incredibly difficult and works you into the ground, you tend to bond with the players around you and I think my experience in banking was like that. I think I learned a lot of really important skills that have helped me start a company. I made more money those two years than I have any years since. So it's only been downhill from there on the financial front.

Chris Erwin:

You're building lots of equity value right now, right?

Nicole Staple:

And I made really, really good friends. It turns out when you're trying to balance a balance sheet at four in the morning, you and your other like 22-year-old friends have a lot to talk about.

Chris Erwin:

Through trauma there is incredible camaraderie and companionship. It is true on the battlefield. I know that through my twin brother in the military.

Nicole Staple:

And I would never compare investment banking and financial modeling, just to be clear, to a battlefield.

Chris Erwin:

I hear you. I mean I was a banker when my brother was in combat abroad in Afghanistan and Iraq. Surprisingly there are some very interesting studies that were done that the highest stress level that a human can have is when you feel that you don't have control over your schedule and that there's incredible uncertainty. And in banking, there's incredible uncertainty because it's 9:00 pm. You think you're done for the night and then a managing director drops like a whole pitch you have to prepare by the next day on your desk. And that that level of stress... This is crazy. It's just what the article says is that that can be higher than those that are in combat and conflict.

Chris Erwin:

Okay. So you're at UBS. You meet this incredible group of people, this incredible network, which you've actually brought up with me in the past. You do that for I think a year or two and then you transition to SVB. What was SVB?

Nicole Staple:

So I did that for two years and then I became really interested actually through working healthcare, in earlier stage healthcare technologies and biotech, and I was deciding between going to work for a biotech company or going to Palo Alto to actually think about learning more about venture capital and made a last-minute decision to do that with Silicon Valley Bank that is deeply ingrained in the startup ecosystem as many of your listeners might know. So I went to work for SVB Capital which is the direct investment fund, essentially the venture capital fund of SVB, small team and that was my first introduction to startups.

Chris Erwin:

So your first introduction to startups, learning about startups and working with early stage founders, what was your initial reaction to that?

Nicole Staple:

My first reaction was there's a lot of people asking for money. I should have known better, but a lot of companies, a lot of ideas, a lot of brilliant people, things I could not understand, I could not for the life of me figure out what the cloud meant.

Chris Erwin:

So there's lots of "cloud conversations".

Nicole Staple:

And this was again, I'm dating myself, new terminology in that day. But I mean really, really inspiring and what I think was interesting is that you were taken seriously whether you were 22 or 52. I think it was really interesting for me, and this is a little bit nuanced but to learn about the life cycle of a company and how things can rise and how things can fall. By doing a lot of cap table analysis, I could actually start to understand like what it meant to own a company, who owned that company, how it all worked and how that evolved as the company grew.

Chris Erwin:

Yeah, that's actually really interesting because probably growing up watching the news media then going to Wellesley and then at UBS, you saw, "Hey, a lot of the founders of companies are our banking clients. They're older, right? They've gone through their careers. Now, they're more established. All of a sudden, you're at SVB. You have people that are maybe right out of college or haven't even gone to college pitching with these really big ideas. And then being empowered to do so, sometimes the bank would write checks.

Chris Erwin:

That's got to feel really exciting to you where, one, you're probably rooting for some of these people that are pitching, have these ideas but also thinking about, "Well, if they can do it, then I could also do that, right?"

Nicole Staple:

Yeah, a little bit. I mean, I felt that for sure. Everyone was smarter than I was, so maybe a little bit more inferiority complex than anything but I think that's something we all battle. That's actually been like I think you hear this a lot, but that's certainly been a big theme as well throughout all of this. I think being in awe of the just raw brain power out in the valley was it was pretty amazing and I could also start to explore like if this world is interesting to me and I do think I want to make an impact somewhere, what's something that I might orient myself towards that I could feel passionate about and understand and be good at.

Chris Erwin:

Interesting. So you do SVB for a couple years and then after that, you have a transition to business school, the Kellogg School of Management at Northwestern and Chicago. I think you did a couple pre-MBA internships in Chicago, but what sparked that transition? What caused you to leave SVB?

Nicole Staple:

I was really interested in potentially starting my own company. And again, much more socially oriented actually, I was really intrigued by social entrepreneurship again. I've had a sort of a theme around being interested in how women move up in sort of society economically. I was interested in that and I was thinking of doing a few different internships prior to business school but ultimately chose year up, which is an amazing national nonprofit that prepares really talented youth for college or really fortune 500 companies through this amazing training program. I thought that I would go to business school to start a social enterprise.

Chris Erwin:

So you thought you would go to business school to start a social enterprise. You'd do this pre-MBA internship at Europe and that further validated your interest in the space like yes, this is definitely what I want to do?

Nicole Staple:

Yes. Although, the one thing I noticed in the nonprofit world because this was a non-profit, but they have an interesting business model where Fortune 500 companies actually essentially fund the model they're not constantly fundraising for grants. But I think most non-profits, you're still particularly as the executive director or the CEO, a lot of your job is asking for money. So there was something that I was noticing there around personal wealth as well, and that was also starting to form in my mind what is the optionality I can build into myself if I think about something that could have financial upside in the near term whether it's starting my own thing or going to a startup or going to another type of job where I could continue to build maybe my own financial footholds, could that lead to more flexibility later on for the type of like social justice work I might want to do?

Chris Erwin:

Interesting. So it's hey, there's a chance you're looking at these early stage companies, founders with these big ideas, raise capital, work really hard, potentially have a liquidity event and exit. And then they are freed up both in time and money to give back and pursue altruistic initiatives. So that seemed like an interesting path for you to take.

Nicole Staple:

You're saying it probably much more eloquently than I would have thought at the time, but I think that's probably along the lines of where my head was at the time.

Chris Erwin:

Okay, interesting. Again, there's clearly a few different ways to do that. It's like you could go into investment banking or consulting, grind that out for 10, 20 years, and also give back. But you were leaning towards the entrepreneurial side. So you go to Kellogg. So that is your focus while you're at school? Are you on that path?

Nicole Staple:

Yeah. I was. I did a lot of work in social investing, social enterprise work and it was a tough industry at the time. It was hard to understand how to build either a fund or companies that were sustainable, double bottom line, sort of initiative. It was complicated. It was more complicated than I thought.

Chris Erwin:

I've never heard of double bottom line actually.

Nicole Staple:

Social return and economic and financial return.

Chris Erwin:

Yeah, I like that.

Nicole Staple:

So how do you balance the two and make them optimized for both. It can be challenging. It was around that time that I met my co-founder. She was doing something completely different, but I was ultimately intrigued by what she was working on as well.

Chris Erwin:

Tell us about that moment. So it seems like that you are working on a few different things at school, double bottom line companies and ideas, but as we know now, Brideside is what took off, but what were the origin days? This was not the first idea that you were working on.

Nicole Staple:

No. Well, this company wasn't the first idea. Well, it wasn't my idea, to put that out there. I was just along for the ride, but it was not the first. My brother and I actually pitched some ideas at Kellogg. We won a little pitch competition around our media idea, around bringing local music into... It was sort of like a pitchfork but more location based where you would merge like content and shows that were happening and content that musicians were putting out by major cities. We had some different ideas there. I had-

Chris Erwin:

So this is your brother, Justin. You're pitching ideas at Kellogg. How much younger is your brother? He wasn't in school with us?

Nicole Staple:

He was in college.

Chris Erwin:

He was in college.

Nicole Staple:

He was at University of Chicago, so just down the south side.

Chris Erwin:

Oh, he was nearby.

Nicole Staple:

Mm-hmm (affirmative).

Chris Erwin:

I did not realize that.

Nicole Staple:

Yep. So you were pitching ideas together and thinking that maybe that could be the thing doubling down on family.

Chris Erwin:

I just try to find people who are smarter than I am and attach myself to them and then pitch their ideas. It was a very smart strategy. It's worked very well for many people. Okay. So you were doing that with your brother and then was any of those ideas seemed like they were going to have legs?

Nicole Staple:

Yeah. I mean, he ended up being very successful in his own right, but Sonali, my co-founder and I were in the same business school section. So we met really day one of school and were friends first. She had been planning her wedding while applying to business school and had thought that the wedding industry was really, to not sound overly trite, ripe for disruption. I knew that she was working on this, but I didn't know much about it. We were in a class together and she said, "Do you want to join my business plan writing team?" I had a few friends on the team, so I thought, "Cool, this looks fun."

Chris Erwin:

Little did you know in that moment when she asked that question that it would literally transform the next nine years of your life.

Nicole Staple:

My entire life.

Chris Erwin:

And potentially many more.

Nicole Staple:

I think there's definitely a power in saying yes to a lot of things and just trying them out. I think I was unsure about whether the wedding industry was interesting to me at all, but I think I was open-minded enough to try to understand the opportunity in a really like detached sort of more like academic way. I immediately thought that it was an awesome opportunity and I could very quickly see where the growth scenario was. And I saw this really like terrible customer experience for women, shopping for bridesmaid dresses and bridal gowns.

Nicole Staple:

I was like, "Oh, yeah. David's Bridal seems like super outdated. Good point." And how these large groups of women were shopping and planning together. It was a huge social thing. I hadn't really been through it much myself, but ultimately would have become a bridesmaid like several times after starting to work on this idea, and I could just see like this is something that feels given where consumer tech is going, given how we're using the internet, how we're looking for inspiration, this just feels like an industry that has not caught up yet. So as we started working on the idea together, I became more and more excited about it.

Chris Erwin:

Wow. Did you feel that you and Sonali really clicked from the beginning? Was there like a special vibe between you?

Nicole Staple:

I did and I never would have started the company if it weren't for that. While we were both MBAs and I think that can sometimes be looked down upon. I felt that we were very different in so many ways, which was a good thing. She was incredibly creative and smart. She had a really interesting orientation towards systems and science. Again, finding people smarter than you are. I was sort of like more of a strategic thinker. I liked big ideas. I could put stories together. I understood again the life cycle of a startup.

Nicole Staple:

I felt that I could really add some direction and structure to some of the ideas that she was talking about with our original co-founder, Emily who's no longer with the company. So I felt we worked really well together. She also was like a self-proclaimed fashion junkie, I was not. I liked more the business side of things and she had a great passion for how to build relationships with designers. She had a great eye for the product. So I just felt that we really vibed.

Chris Erwin:

This might have been a bit premature, but did that complementary relationship also gets you excited where it's like, "Hey, this is a really good idea. And if this were to go somewhere, just sort of become a thing, this could be someone that I could actually work with. Not only just like I like her, but no, we actually work well together. We enhance one another." Was that flashing through your mind?

Nicole Staple:

For sure. And those early days, it's like dating for the first time, meeting someone you really like when you're in those like early days.

Chris Erwin:

Nicole just did a little like shoulder shimming that was part of that. I wish you guys could see it.

Nicole Staple:

Yeah. It's like all romantic and fun like pillow talk until three in the morning. You just you know the ideas are flowing. You're starting to realize, "Oh my god, there is definitely some chemistry here. Some founder chemistry." And those days are really exciting because the whole world is literally at your fingertips when you feel that way.

Chris Erwin:

Yeah. It's a really, really exciting moment. I mean, this is like ridiculous about MBAs, when you start talking through a new idea with someone, you're like, "Could this be the rest of my life? Is this my billion dollar exit?" We probably ask ourselves that question too often while in school. But it is a really exciting moment. That's the fun of it.

Nicole Staple:

Yeah. Our spring break, second year, we hiked Patagonia with some friends and we spent hours on the trail like beautiful landscape. So special to be able to do that and do that together and just talked about what the rest of our lives would sort of look like. Could we do this? Could we take the leap? I often think business-minded people and ambitious people over index for risk. I think a lot of MBAs do that. They think things are more risky than they actually are and that can create a lot of fear or inhibit you from exploring new opportunities like this.

Nicole Staple:

I was like really glad that she had decided to do this sort of irregardless of whether I was on board or not and I think that provided a lot of inspiration for me and comfort knowing that she was in, and we could be buddies in that and I could just take the leap. At the end of the day, we'd be in it together. If it failed, I'm sure we were employable. It was not going to be that big a risk.

Chris Erwin:

All right. So let's fast forward a little bit. So you guys commit. You want to do Brideside. This is what you're going to do after you graduate from Kellogg. Okay. So school is over. What does the team look like and what are you working on? Do you have financing?

Nicole Staple:

The team was our friend, Emily, Sonali and myself. We quickly got sort of a technology UX/UI co-founder. That summer after we graduated, we started the Monday after graduation working full-time at 1871, which now is a massive incubator and co-working space in Chicago. We are one of their first tenants and we just used the Kellogg room and started working on...

Chris Erwin:

There's a designated Kellogg room.

Nicole Staple:

There is a Kellogg room and there were only like us... Basically, it was just us using it at the time. This is again, startups weren't as sexy as they are now and we did a photo shoot. We were designing a homepage. I remember that we were coming up with the name. All really important things and we were applying to incubators. That's my memory. I was sleeping on Sonali's couch, me, her husband, all in her apartment for that summer and applying to an incubator became like the primary milestone because that's how we felt we could properly organize, incorporate launch, potentially get some early stage funding.

Chris Erwin:

Okay. Did you eventually join an incubator?

Nicole Staple:

We did. It was called Dream Adventures out of Philadelphia. One of the founders of David's Bridal was involved in the incubator and that was why we chose that one and he became our mentor during those three and a half months.

Chris Erwin:

Interesting. Okay. So you get into Dream Adventures. Helpful experience?

Nicole Staple:

It was really helpful. I think we realized the value more and more once we left. It created a discipline that I think can be hard to create yourself if you're a first-time founder, which is being held accountable to KPIs every single week even when you don't really have a business. It caused us to do things very, very quickly. It removed us from our friends and family. We were in the same apartments and pens campus. And I think it allowed us to focus-

Chris Erwin:

So you were down in Philadelphia.

Nicole Staple:

We were down in Philadelphia. It allowed us to focus.

Chris Erwin:

Okay.

Nicole Staple:

And we ultimately raised some capital after it, which was obviously pivotal to being able to launch the business.

Chris Erwin:

So was there a demo day at the end?

Nicole Staple:

There was.

Chris Erwin:

And you raised some money from that demo day?

Nicole Staple:

We raised around 250,000 I think out of the gates and I believe that year, we raised another 250. So maybe 500 came out of that initial demo day.

Chris Erwin:

Wow. So this is exciting. You meet Sonali in your MBA program. You have the idea. You commit to it after graduation. You're working on it. You get into the incubator like check, then you raise some seed capital check. So you guys must be feeling like, "All right. Here we go. We're on this path. Things are looking up." Is that what you were feeling at the time?

Nicole Staple:

I feel like we felt desperate all the time. A lot of things were happening though. Sonali found out she was pregnant the day our incubator started. The day we launched our first pop-up shop which was like our coming out party of the whole thing was the day she had her baby.

Chris Erwin:

Wow. Okay.

Nicole Staple:

So April 5th, 2013 was the day we essentially early sort of beta launched Brideside the day she had the baby. So nothing in our history has ever been smooth. In fact, our first investment that was actually going to truly allow us to pay ourselves like a little bit of money which we ultimately weren't able to do for a while was through a large angel group in Philadelphia and we thought we had the investment. One of the managing partners from the group was doing a final meet and greet in Chicago, flew in to meet us. I don't think they knew Sonali was pregnant and we never mention it. She was eight months pregnant. She was big. He came, he left and they told us they were passing because we were located in Chicago. You have to ask yourself is that really why they passed on the deal? It was very tough for both of us.

Chris Erwin:

Yeah. You thought that you had that investment like in the bag. It was all sorted. And then that just changes. That's interesting. So I mean, one, looking from outside, people think like wow, this is a team that's really checking the boxes. They're growing. They've raised money. Through the incubator, they're learning. They have a beta test. But on the inside, you guys felt like, "Oh, we're just like every day, we're struggling through this." Just barely getting through these milestones. It's exciting but there's just so much more to do. No guarantees of success.

Nicole Staple:

Yeah. When you're feeling broke, you have tons of student loans. You are trying to get something off the ground and nothing feels like it's working. I think it became very obvious at that moment that we were also women in this industry.

Chris Erwin:

Explain that.

Nicole Staple:

Well, Sonali being pregnant I think was the reason that we lost that investment. I think that was very obvious to us at the time. So the reality of how we were perceived by this investment community and by the startup community actually became like very real at that point and I think you know Sonali got a lot of questions, "How can you be a mom and a startup founder?" I think there was a lot of bias at the time there and that was just becoming very clear to us that that was a factor.

Chris Erwin:

You're being punished for who you are and your identity which is probably an accelerant to your business because you intimately understand the bridesmaid's journey and that investors are punishing you for that. That's got to be so frustrating.

Nicole Staple:

Yeah. I think, look. I think there's just biases that are out there and I think you can feel sometimes like you're being held to a different standard, but ultimately that came and went and that was a reality. There was like a triple whammy as we scaled our business that year around fundraising. It was very tough for us. One was, I think being women founders but having a women focused consumer business. A lot of early stage investors are investing based on passion or just something that they personally care about, which is understandable. It's usually their personal money of their high net worth. When men generally control 90 to 95% of that capital, they just don't orient towards a woman's consumer product. They don't understand. So that was one.

Chris Erwin:

I can't relate to it.

Nicole Staple:

I think the biases of being a new mom, having a co-founder, that new mom or being young women founders, there's probably unconscious bias there being in the Midwest, less than 5% of capital at the time was going towards Midwest companies. Being in weddings and being in consumer generally less than 5% of VC goes to consumer goods businesses. So I think there was just a lot working against us that I didn't even realize at the time. So you put a lot of pressure on yourself. I spent a lot of years just thinking that everything that didn't go our way was like directly my fault and I think now I have a little bit more perspective for just how hard it is for everyone.

Chris Erwin:

Yeah. But as you start to reflect on that, did that make you think like, "Hey, the odds are against us. This might just not be possible."

Nicole Staple:

There have been many moments in the business where we were unsure whether we would be able to move forward and some of that uncertainty was... A lot of times, it was capital related. Sometimes there were moments operationally where we were like is this growing as fast as it should? Is this working? Is it not working? But there was one of those moments that I think was fundraising related where Sonali and I were at a restaurant down the street from our co-working space and we were having the conversation, "Do we keep going?"

Chris Erwin:

Oh, wow.

Nicole Staple:

I was started getting really emotional and crying at the table.

Chris Erwin:

What year was this?

Nicole Staple:

This conversation was probably 2015 at that point. And we were eating Shishito peppers as an appetizer.

Chris Erwin:

Okay. Good memory.

Nicole Staple:

And the waitress came over and said, "Is everything okay over here?" Because I was visibly upset and I told her I got one of the really spicy ones. I just remember that so well because it was really funny in the moment and I sort of pulled it together. One thing Sonali and I have always been really proud of is that in those moments, we've always stayed true to some of the key metrics in our business that allowed us to make the decision. So while it definitely is our baby and our passion project on some level, I think we've always had a very practical approach to the business.

Nicole Staple:

That's important because you're managing investors money and you're also managing people who are relying on you for a job. I think it's very important to be clear headed in these decisions on whether how fast you scale up or down or whether you go on or not and we always had some very key metrics around how likely a customer was to buy from us if she had heard about us and signed up for the site and how much she was spending with us. That became sort of our tried and true barometer and we ultimately were always very strong on that and also actually Net Promoter Score customer satisfaction like how much people liked our product. We were, say, very, very close to those numbers from literally day one in the business and that allowed us to navigate those decisions. And if we felt that those numbers were exceptionally good, we would keep going.

Chris Erwin:

When did you feel that after that conversation, there was an inflection point where like, "Okay, we really have something here and you're like the investor interest is, it's really starting to gel and manifest. Real money is flowing our way." What was that next moment?

Nicole Staple:

I think when we moved to a real office that became a moment for us. We moved to this really cool refurbished warehouse in the west loop where we still have our headquarters. At the time, it was 4,200 square feet. And I say at the time, because we've now taken over like the whole building. And 4,200 square feet seemed like massive to us and we decided... We had experimented in our co-working space with showrooming having women come in and try on dresses in person and it was astonishing to us that groups of women would buzz up to an office and try on dresses in a 200 square foot space literally running around in their bras and underwears in the hallway to try on dresses with us when we were literally less than 10 minutes away from some of the nicest bridal salons in the city.

Chris Erwin:

Wow, yeah.

Nicole Staple:

So we decided something there was working. So we got this new office and we decided the front part was going to be this cool lofty showroom experience and the back part was going to be our office, but it felt massive. So we said, "Okay, we'll lease it out to other companies. We'll try to recoup some of our rent expense." Within a few weeks, we felt like we were already busting out of the seams on that space."

Chris Erwin:

Oh, wow. Exciting.

Nicole Staple:

So that really felt like exciting. I was so proud to show people our real office and the showroom experience, we outfitted it for like $3,000 and within a year, it was like doing over a million bucks with people coming to try on dresses there.

Chris Erwin:

What year is this?

Nicole Staple:

This was in 2016.

Chris Erwin:

Okay, wow.

Nicole Staple:

And so we felt that we were really tapping into something with the showrooming experience. That was also giving us more insight into the customer experience more generally, which was helping inform our technology experience and our digital styling as well, which has become a huge differentiator for Brideside. We never took our eye off the prize on delivering an exceptional customer experience and we continued to invest in that, and that's very much what we're known for today. So we felt that we were really carving out something different. And then the next summer I think in 2017, we had one of our largest wholesale partners, brands, designers, went bankrupt essentially overnight.

Chris Erwin:

Wow.

Nicole Staple:

That was a huge moment for us because a lot of things happened then. We could have totally lost our shirts as a business, but we made a lot of really good decisions at that moment that ultimately led to us creating a growth strategy that would involve us becoming more direct to consumer manufacturing our own product, expanding the showroom experience while continuing to expand the technology experience. And I think that gave us a really defensible business model for mass scale.

Chris Erwin:

So this is an interesting moment to pause on because I know from having known Nicole now from early days of business school, in her business journey that in the beginning challenging and raising capital. And there was other companies that had actually raised... Doing something similar to what you were doing direct to consumer in the wedding industry and in retail that raising multiples of what you had raised. I know that that was really challenging and frustrating for you. But something we always talked about was like Nicole, you guys are super sharp operators. You have good KPIs in place. You have something here. Stay lean and stay resilient, and you did. Then at this point. I think around 2017, 2018, there are some of these competitors that started to fall by the wayside, were no longer around. Tell us about that moment.

Nicole Staple:

When the competitive landscape started to really shift both big players and smaller players and venture back players were, as you sort of put it, falling to the wayside or going out of business or the businesses were being acquired, we definitely felt that there was an opportunity opening up for us and we wanted to very much go at it full force. I mentioned I think the opportunity was really this completely integrated model where we were manufacturing our own products, so higher margin structure. We were able to deliver product faster and a more competitive price point to our customers. We had more control over product design.

Nicole Staple:

We now knew how to do showrooms. We had done a partnership with Hudson's bay company and some Lord and Taylor stores to experiment with that. So we were sort of ready to scale that. We were still really well known for our service experience and just this like concierge stylist experience. We had seen what we believed were cracks in other business models out there, some of our competitors and we felt that, "Hey, we're still growing." We've been really lean from a capital perspective. We were always really disciplined about customer acquisition. We've always been profitable on customer acquisition and we felt that some of our competitors for whatever reason, probably a lot of venture capital pressure had maybe been forced to grow more quickly than the business could sustain.

Nicole Staple:

So we felt that it was really our time. We had to wait for the dust to settle a little bit because it was a very unfriendly environment for us to raise capital at that point because there had been so much negative press around the wed tech space, the wedding technology.

Chris Erwin:

Wed tech?

Nicole Staple:

Wed tech. That's what it was called at the time. So we waited it out a little bit and when we were ready to really scale actually our private label, we had actually already started to scale our private label. That's when we went out for a larger round.

Chris Erwin:

And when was this?

Nicole Staple:

That would have been the end of 2018.

Chris Erwin:

End of 2018?

Nicole Staple:

Yeah. So we had raised 6.2 million up until that point and we wanted to raise a 7 million series A.

Chris Erwin:

On top of that 6 million?

Nicole Staple:

Mm-hmm (affirmative).

Chris Erwin:

And did you feel at this point when your competitors are, as I said falling by the wayside, did this feel validating to you? Did it get you excited or was there another feeling that you had?

Nicole Staple:

I think on some level it was validating and that it's hard for everyone. I think there's a lot of FOMO or inferiority stuff going on in your head in this world particularly if you read like TechCrunch every day. You always feel like everyone's doing better than you are. But what I realized is that we were actually doing pretty well. We had generated quite a good amount of sales volume on a relatively small amount of capital. We had proven a lot out. We were acquiring customers profitably and we felt that we had a lot ahead of us.

Nicole Staple:

So in that sense I think it felt validating, but for me if anything, it's a constant reminder around being prudent operators and really responsible stewards of capital. I think you are always rooting for any other founder around you. I mean, you look up to them. You want to learn from people who are starting companies and scaling companies around you and you never want to see a company fail even if it is a competitor. I guess there's some pleasure in that, but at the end of the day you have to look at yourself in the mirror and say like, "Gosh, I better make sure that that's not me tomorrow."

Chris Erwin:

It's really interesting how you put that. I mean, essentially you're describing how you look at the world as positive some, because if this is all hard all around and if another entrepreneur is succeeding, then there's chance for me as well versus... I know being realistic and many of us will go on LinkedIn and we scroll through like look at them, they've raised all this money or they've gotten this new job promotion and it's hard not to be jealous.

Chris Erwin:

Now, we're talking about broader issues with comparison culture and social media. I think it's really thoughtful Nicole how you described it. This is hard for everybody and we all want to win. There is space for all of us to rise up together.

Nicole Staple:

Right, right. Absolutely.

Chris Erwin:

Just a little anecdote from this before we get on to the next area. With my consulting firm, I was actually advising one of the wed tech companies that was in Nicole's fear. I think I remember telling Nicole that I was going to... I was giving her a preview. I was going to take on this assignment. And I just know during this moment that you're probably thinking through a lot of things through the future of your business. How did it feel when I asked you about that? This might be an interesting reflection of the head space of an entrepreneur.

Nicole Staple:

Well, you asked me if it was okay and I said no.

Chris Erwin:

There's a little bit more nuances of the conversation. But okay, you didn't want me to take on the assignment.

Nicole Staple:

I didn't.

Chris Erwin:

And why was that?

Nicole Staple:

Well, everything felt personal.

Chris Erwin:

Because I'm very smart and I was just going to...

Nicole Staple:

Yeah. You were too smart and you were going to give them... Well, it was a few things. One, is that I think that as an entrepreneur I've tended to probably be, as I am being in this podcast right now, overly transparent and open. I think it's important to learn about the ups and downs of a startup and I confided in a lot of my business school friends mostly around the downs because the ups, you don't need help on the ups. Those are great. They happen all the time for us.

Nicole Staple:

I don't want to make it seem like it's all downs, but the downs are the really tough part in your job as a CEO or a founder is to constantly deal with the down. So I felt like I had been really transparent with you about those. So you going into another business knowing all my secrets, made me uncomfortable but then also like everything with the business at the time, it felt personal. I was saying I hold a personal grudge against every single friend or family member who got married or was in a wedding and didn't buy a Brideside dress.

Chris Erwin:

Yes, understood. To bring up this conversation not to debate whether proceeding was right or wrong or anything like that because my belief-

Nicole Staple:

It was fine ultimately.

Chris Erwin:

Yeah. My belief was it was a company with a bit of a different business model, but I think it was more like... What's interesting is just the emotional reaction that it was just, "Hey, I look to my peers for help and guidance." And this felt like just a personal saying, "Hey, maybe this person is not going to be more focused on helping another company." And I really need all the help and all the emotional support I can get.

Nicole Staple:

And sure. In retrospect, was that emotional reaction the right one? Probably not.

Chris Erwin:

I think it worked out for us. We're having a podcast right now. Nicole agreed to be on it. So we are not mortal enemies.

Nicole Staple:

We're good friends. We're still good friends.

Chris Erwin:

We are still good friends. It worked out. So we're going to talk about a big defining moment that happened in Nicole's personal and professional career I think between 2018 and 2019. Professionally, I think you raise your largest round of financing to date, I think around, I'll call it 6 to $7 million. In addition to this, your husband was also diagnosed with a very severe form of cancer, kind of concurrently all around the same time. Tell us about this moment.

Nicole Staple:

In early 2018, my husband and I were coming back from a Hawaiian vacation where he hadn't been feeling well and it ultimately led to a diagnosis of cholangiocarcinoma which is very rare cancer of the bile ducts. So around that time, we were forced for his medical treatment to move to Rochester, Minnesota where he received a liver transplant summer of 2018.

Chris Erwin:

From his twin brother.

Nicole Staple:

From his twin brother, which was essentially 75 to 80% of people have essentially long-term survival. It can be curative. The cancer they remove, the cancerous organ and after that, we spent several months in Jacksonville, Wyoming for his recovery, in LA with you to be in warmer weather. And throughout that time is when a lot of this competitive shake-up was happening. We were also preparing to raise that growth equity round. It was incredibly tough, obviously. We thought though things were sort of on the up and up.

Chris Erwin:

For Eric.

Nicole Staple:

For Eric. So it more became a matter of balancing, working remotely and I was his primary caretaker. He took on an incredibly anti-vegan, anti-cancer diet. So cooking became a big part of my life and spending time together and taking care of him, and also running the business.

Chris Erwin:

Running the business as the CEO of this... How big was your team at this point?

Nicole Staple:

We were probably nearing 50 or 60 people at this point and during that time, we went through a potential M&A. We almost got acquired. We almost acquired two other companies at that time. So there was a lot going on, balancing a lot of different things. And then very unfortunately as their financing round was picking up in May 2019, Eric became ill again just under a year after his transplant and they found that there was micro metastasis in the bottom of his bile duct in this one area they didn't remove and it ultimately became terminal at that point.

Nicole Staple:

So he was airlifted. I'm leaving out a lot of details, but airlifted back to the Mayo Clinic in Minnesota and as we were receiving that terminal diagnosis, I was literally finalizing disclosure agreements on a round.

Chris Erwin:

Geez.

Nicole Staple:

So it was taking phone calls from waiting rooms and hospital rooms sort of non-stop for several weeks.

Chris Erwin:

Okay. In this moment, this is like an unfathomable moment for pretty much 99.9% of the population. You have so much going on in your life. Did you feel that this was unsustainable? Did you feel that you were just going to crumble, but it was every day, just get through the next day or did you have this feeling at the moment of, "No, you got this. I'm an all-powerful CEO and wife, and I'm just going to power through"? What was going through your head?

Nicole Staple:

I think I felt a deep responsibility to the company. We needed the capital, we needed to close the round and it was really important for me to stay clear-headed and disciplined enough to make that happen. I also felt that a lot of the ways that we had handled my husband's illness was around really coming up with an action plan and an educated one as quickly as possible. That was sort of how we had handled the entire illness, and that became no different either.

Nicole Staple:

So I immediately pulled together a squad team. We came up with a plan to do as much research as possible around the new options that we had mobilized a lot of people on different parts of research and talking to new doctors because at this point the options became increasingly more limited and we had to think more out of the box more away from traditional medicine and he was also going through a lot medically at that time and he needed to be stabilized.

Nicole Staple:

So it was sort of just firing on all cylinders at that point to sort of get it done and obviously trying to be as optimistic about his outcomes as we could sort of like the time we could buy ourselves, whether it be options for us and clinical trials or things like that.

Chris Erwin:

You're taking essentially like a business approach of how you built Brideside to his cancer treatment.

Nicole Staple:

Yeah, absolutely.

Chris Erwin:

And just thinking like, "Hey, here's a problem. Let's come up with a solution. Let's do a research and figure out different ways going forward." In doing that, that it's a very smart approach, but was that also a way for you to just have comfort and how to deal with it which is we have a process, we get into it, power forward?

Nicole Staple:

Yeah, absolutely. And I think my husband was oriented towards that way too. I think it made having sort of hope, made a plan, made things feel better. So in that moment, that's what we were thinking, but I think the thing with cancer is you don't know where you are on the clock, ever. You don't know how far... At that point, he had no metastasis. We didn't know how long we had and we were still just adjusting to this reality. I mean, it was really unfathomable to us. We felt that he had done everything right and we had caught it early and that he was going to be fine. So we were really adjusting to this reality real time and so I think that was the reason we were just trying to get through it and he was just trying to get healthy. He was going through a lot medically.

Nicole Staple:

So this was May 2019. We closed around literally the exact same time he got diagnosed and then when we closed around, we had already lined up a lot of new hires. We were about to sign a bunch of leases for showrooms. So literally the day after the round closed, our head of people and culture came on, our CFO came on board. We signed several leases within that first several weeks. We started scaling up our sales team. A lot happened right then, and I think it was really over the next two or three months that it became sort of unimaginable to manage all of those things.

Nicole Staple:

But the one thing that I'm really proud of from that time is that I do think that I made the space to spend time with my husband. And I think overall, after his diagnosis while it sounds like I was managing a lot which I was and certainly probably worked too much, I do think that we... It was the first time I had truly prioritized something and someone else ahead of the business to be honest even though we had been married for almost five years at that point.

Chris Erwin:

Yeah. And I was at your beautiful wedding in Victor, Idaho.

Nicole Staple:

So I do think it was an important lesson around, I wasn't a mom. I think oftentimes people, or a dad, will find being a parent like forces you to do that, and we didn't have kids. So I think like this forced me to do that.

Chris Erwin:

Wow. So I mean, I just want to pause on this. You just have for the first time since you had graduated business school and working on Brideside, this was the first time that you would prioritized something else other than the business.

Nicole Staple:

Yes.

Chris Erwin:

That's a big statement. I mean, that's-

Nicole Staple:

It's really true.

Chris Erwin:

It's like eight years of your life. I mean, it clearly just shows your commitment to the Brideside and the team and the mission, the problem that you're solving in the industry. But I think it's also reflects on just entrepreneurs that can get lost in their business for better or for worse. So this is probably a unique moment where the business has needed you for many years and Eric, and the family also really needed you. Being as one of Eric's very close friends needed you as well. A good life lesson to think about too is balance going forward. Do you feel that that lesson is something you're applying going forward?

Nicole Staple:

Yeah, 100%. So your listeners know how this ended up. We were sort of like in May of that year, he passed away, August 12th of 2019. So I think now the reality is that I have a new life and that's a very important reality for me to sort of embrace and that it's never going to be like it was. Sonali, my co-founder who is also very good friends with Eric, we got together shortly after he passed away and we said Brideside has been this amazing journey that we've built. We were on our way to doubling the size of the team at this point. We're growing very fast and we said nothing that happened before is actually really relevant for what the future brings. Nothing is going to be the same in how we interacted as friends and as couple friends. Socially, the company is at an entirely new place and I think there's something incredibly liberating about that feeling.

Chris Erwin:

That is a powerful statement. I intimately witnessed you, Nicole during this period and you're an incredible pillar of strength for all of us around this. And just speaking to all of you investors and potential executive recruits for Nicole going forward, everything that I've seen her manage throughout every single aspect of her life is so impressive. So I would back this woman with anything, with any unlimited amounts of capital. That being said just, it's such an incredible story and appreciate you sharing that for everybody.

Chris Erwin:

So next up, this is the last segment before we get into our very exciting fire round, but Nicole, you're now in Brooklyn. You've moved to New York City. You're living here. You have a new flagship store on 20 East 20th. It's 2020, what's next up for Brideside?

Nicole Staple:

We just launched bridal gown. So as I mentioned before, we used to be just bridesmaid dresses, but now we are doing it all. So we have private label bridal gowns. We sell some top designers. We have these beautiful showrooms. We just launched a few new cities. So we launched a new big flagship in Chicago. We launched on Newbury Street in Boston.

Chris Erwin:

Wow.

Nicole Staple:

As you mentioned, we just launched bridal in New York and now we have a big store here. So we are really looking to take over the world at this point. That's pretty much what it comes down to. We have this tribe. We're now almost 130 teammates, predominantly women across all functions, all levels, operations technology.

Chris Erwin:

Predominantly women, is that like 60%?

Nicole Staple:

Like 96%.

Chris Erwin:

96% women. Okay, yeah. Global domination by women.

Nicole Staple:

Yep. We are a very diverse tribe in terms of some aspects of our makeup and others not so much, but we'll continue to build diversity into our culture. We are not only focused on the top-line growth story, but we are really focused on who we are as a company right now. I think that's something that is really, really hard to do when you're working on a lean budget and you're just trying to make it and continue to grow and prove yourself to the world, but we are super focused on who we are as a culture at how we create a company of belonging, how we're progressive and the types of policies that we're making for women and that has become a major focus for us as well.

Chris Erwin:

Got it. Wow. I'm just looking at Nicole's face light up during this conversation. So very exciting times ahead. What would you say is your favorite part of this job? Of all the many hats that you wear and everything that you do, what's your favorite part?

Nicole Staple:

It's a good question and like my co-founder said a long time ago, if it's not fun, it isn't worth it. It definitely always hasn't been fun, but I think now, I'm really working on embracing the fun and like the silly moments. In fact, Sonali and I now don't end a meeting without either singing a made-up rap lyric or recommending a song to one another. We're trying to bring in that playfulness into the day and that is really, I think what it's all about particularly around our people. So I have to say my favorite part is like getting to hang out with the amazing people that believe in us and believe in the mission and come to work every day.

Chris Erwin:

Wow. Can you share a recent rap lyric that you came up with Sonali?

Nicole Staple:

That is private founder business.

Chris Erwin:

There's an intimate relationship that's formed between Sonali and Nicole and I don't want to get in the way of that. Understood. Before I fully let you off on moving to some of the easier questions, let's talk about the direct-to-consumer industry as a whole, right? There's some challenges that are emerging in real time. Casper, one of the big name direct consumer brands has raised lots of capital, just went public. I think some people are looking at their IPO as... It's now trading at a discount to its IPO stock price.

Chris Erwin:

Recently, I think the CEO and founder of Outdoor Voices just stepped down. They're having some challenges with their user acquisition and their growth. I think a lot of people were talking about just growing saturation of user acquisition channels. It's becoming more expensive to run these businesses, and a few other factors. You hear about this in the industry in which you operate. How do you feel during all this? What's going through your mind?

Nicole Staple:

I mean, it's scary. I do think there's some softening. There's definitely some softening in the consumer markets across all industries for sure and we're seeing that in our industry too. For us, we are really dedicated to discipline and that is just how we're trying to position ourselves to navigate through any unexpected ups and downs. Historically our businesses has been relatively predictable in some ways around user acquisition. And the sales people have to get married. When they sign up, we know when they're going to get married and it can be predictable.

Nicole Staple:

So I think for us, it's really about scenario planning and downside protection to make sure that in a worst-case scenario, we're still protecting our investors and we're protecting our people. So we continue to just be really maniacally focused on the metrics that we talked about from day one, really and continuing to be really nimble. I think if you build flexibility into your model around manufacturing your own product, which channels, you can sell on digital versus brick and mortar, I think we can flex each one relatively seamlessly. So I think just remaining incredibly focused on results and not getting ahead of our skis on growth is what we're going to do.

Chris Erwin:

All right. Let's move into the closing and rapid fire questions. Are you ready for this Nicole?

Nicole Staple:

I'm ready.

Chris Erwin:

Okay. I don't think Nicole can get closer to the mic than where she is right now. All right. So there's, I think about seven questions that we have here. So let's get into it. Proudest accomplishment of your Brideside career?

Nicole Staple:

Okay. So definitely that time our big designer went out of business. We all gathered at the office. At midnight when we heard they were filing chapter seven, my co-founder called their factory that night, we had to make a lot of real-time decisions that could have involved not being 100% honest to our consumers. There's a lot of uncertainty in that moment around protecting our own exposure, what to tell our customers. Do we refund dresses?

Nicole Staple:

We weren't sure if we were going to be able to deliver dresses, but we made a bunch of decisions based on our values as a company that night and really rallied, and it ended up being amazing. I think it was like one of our proudest moments as a company just seeing everyone come together for it.

Chris Erwin:

Wow, that's awesome. Great, story. All right, 2020. What do you want to do less and more of this year?

Nicole Staple:

I want to do more reading, which was a theme for me over the past year and so I've been committed to taking more quiet time for myself to read and reflect. I want to do more with my hands.

Chris Erwin:

Do more with your hands, what does that mean?

Nicole Staple:

Less typey-typey. So I actually have a typewriter now. So I've been trying experimenting writing more on a typewriter instead of just a laptop. But I would love to be more crafty with my hands generally. Just be able to like fix more things, build more things. So I'm starting to think about what I could do there. I want to do less Netflix.

Chris Erwin:

Less Netflix. Do you think you watch a lot of Netflix?

Nicole Staple:

Actually, since I've been in New York I haven't been Netflixing as Netflix seems a thing.

Chris Erwin:

You see Netflix and chill, but you're at the avant-garde of media. So Netflixing is a new thing.

Nicole Staple:

I'm going to Netflixing. I've been doing less Netflixing in the city because I can-

Chris Erwin:

#Netflixing.

Nicole Staple:

There's so much to do here. Yeah, hashtag. So yeah less Netflixing more reading.

Chris Erwin:

Got it. I like that. Entrepreneurial advice. What one to two personal characteristics primarily drive your success? What do you think?

Nicole Staple:

Oh, man. I mean the first is just grit. I think the resilience and grit, like this shit can be... Sorry, if you have to bleep that, can be really a marathon and not a sprint. And I think like getting off your ass over and over again can be really, really important. Just figuring out that north star and not losing sight of it, is really important. I think the second thing, which we've talked about a little bit is I've done a lot of exploration over the past few years on sort of how I am received by others.

Nicole Staple:

I think one of the things that I've really enjoyed learning about myself is a deeper understanding of my personality and my communication style and how that is very effective in front of certain people like investors or our board, and how maybe when you're talking to a junior employee or someone who it just is oriented completely differently than you, how that can be perceived. It's so important. It's so important in building culture and relationships with your employees and your team, and I think I've learned a lot about myself there and have become a better operator and founder because of it.

Chris Erwin:

All right. So last three. We're going to make these rapid, rapid fire.

Nicole Staple:

So stop talking so much. Got it.

Chris Erwin:

One to two sciences responses. But this is great. You're a gem.

Nicole Staple:

I feel like these are heavy questions.

Chris Erwin:

Just part of the challenge that you signed up for. All right. Last three advice for director consumer professionals going into 2020.

Nicole Staple:

Cash, manage it well.

Chris Erwin:

Manage your cash well. Words of wisdom. Second to last question, any future startup ambitions?

Nicole Staple:

One or two words, cool. Yes.

Chris Erwin:

You can say a little bit more.

Nicole Staple:

More social justice oriented. I mean, I'm really passionate, I'm really very concerned about the climate and I really love the idea-

Chris Erwin:

Environmental climate.

Nicole Staple:

Yeah. So I really love the idea of how you connect job opportunities back to also like environmental opportunities and ways we can do that better.

Chris Erwin:

Lastly, it's pretty easy one. After hearing this amazing story, how can people get in contact with you, investors, partners, whoever else, designers?

Nicole Staple:

Brideside.com. You can go check it out sign up and on Instagram @brideside.

Chris Erwin:

Easy. All right. Thank you, Nicole. This was a lot of fun.

Nicole Staple:

Yeah, this is awesome. Thanks, Chris.

Chris Erwin:

Wow. That interview was super fun. I felt I knew Nicole's whole Brideside story before we even sat down for this interview. But I actually learned a lot of new things about her during this recording and I'm even more impressed and inspired by her. I can't believe that was even possible. And that's what makes this podcast so fun. I get to learn more about some of my favorite people on the planet and then get to share their amazing stories with all of you. And this is just the first episode.

Chris Erwin:

We have so many more awesome interviews lined up, so stay tuned. Our next interview features Adam Sachs, the COO of Team Coco and podcaster extraordinaire. We actually grew up in Jersey together, so there's some fun history between us. That episode will drop later this month so be on the lookout.

Chris Erwin:

The Come Up is written and hosted by me, Chris Erwin and is a production of RockWater Industries. Please rate and review this show on Apple Podcast and remember to subscribe wherever you listen to our show. And if you really dig us, feel free to forward The Come Up to a friend. You can sign up for our company newsletter at wearerockwater.com/newsletter. And you can follow us on Twitter @tcupod. 

The Come Up is engineered by Daniel Tureck. Music is by Devon Bryant. Logo and branding is by Kevin Zazzali. And special thanks to Andrew Cohen and Sean Diep from the RockWater team.

Introducing a new podcast featuring entrepreneurs and executives who are shaking things up and building exciting new companies. In industries like New Hollywood, podcasting, ecommerce, and the metaverse. Entertaining you with stories you won't hear anywhere else, from the next generation of leaders who are going to change the world.

Brought to you by Chris Erwin, the founder of RockWater and 15-year operator, seller, and investor of companies operating at the intersection of media, technology, and commerce.

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