Stairway to CEO

• What it was like to grow up as the eldest of five in Ireland in a family of entrepreneurs who are third generation manufacturers of construction clothing and why she went into tech
• Why her dad encouraged her to go study business instead of dietetics and why she saw the wisdom in that later
• What moved her over to California to work for Google and then Airbnb
• What her experiences at Airbnb taught her about how to create a healthy family culture within a company and not just grow fast, but grow well with a strong team
• What brought about the need in Laura’s life for a company like Bobbie and what compelled her to develop a product and work on it for four years before launching
• Why she believes confidence and great referrals from past experiences are helpful in raising funds with investors, even if you don’t have metrics yet to share
• How fundraising has gone for Bobbie through traditional VC funding and also the nontraditional raising through Republic, which has including over 200 moms
• What the process of obtaining the FDA green light was like, what lessons came through it, and why it is the way it is
• What great advice she has on how to successfully lead a startup and what is next for Bobbie

HiBobbie.com

“Becoming an entrepreneur myself now, have I realized that the currency to join a startup is really energy. It's passion. It’s your connection to what’s being built.”

“And it was during this I realized I love fast-growth companies. I love being in the middle of it. I loved being on call at random hours because that kind of adrenaline to be building something that wasn't just a massive revenue driver, but it was a culture changer is so impactful.”

“I think that's part of an entrepreneurial journey, which is, you spot opportunities by seeing the ridiculousness of why certain things are the way they are.”

“It continued to hit me that they are buying into my passion, my confidence, my ability to execute. What I had was, very fortunately, a decade of experience in the tech world and fast-growing companies to be able to point to to show that I did have a track record of getting shit done.”

“We were very intentional about spending the two years prior to launching and building community. And often products and companies will say, ‘well you can't do that until you have a product on the market.’ And for us, it wasn't just about the product, it was about shaking the stigma, having the conversation.” 

“When we went to market, we had hundreds of moms who were dying to share that we had just launched. I believe that is kind of the secret sauce of what allowed the business to take off.”

“It was an education of the industry that we are about to walk into. We are walking into an industry that is heavily regulated with massive companies watching your every move.”

“The people that you find that are completely irreplaceable for you, you give them the world because they are worth the world. Your entire company goes around because of the people that you hire and how you recognize them, reward them, support them.” 

“There are hands down people that give me the sweats at night if I thought about losing them...because they truly are founders, owners, developers of this business more than myself. They are incredible.”

“As a CEO, your job is to build the machine that runs, and every component of that machine is its people.”

“How you support the exit of an individual in the business will say everything about your leadership.”

• How his childhood was full of the love of food and exposure to business and learning how to make money, even from an early age
• What hard lessons he learned from mistakes in business while in college and how what he calls his first real business really grew and provided a lot of opportunity with nationwide clients
• What it was like to have a successful experience in an acqui-hire with NOISE that was an amazing partnership for Andrew and what he did next with recruiting solutions
• What led him into financial management and consulting, to part time CFO roles, and lead to a full time CFO position
• How the idea for Otamot came to him, what he did differently with this idea compared to other ideas he had over the years, and why he chose the name Otamot
• Why they were able to hit the ground running after launching Otamot, how he got in front of more buyers, and his advice on marketing and pricing strategy
• How he balances his full time, 9-5 job, with his 5-9 job growing Otamot and what advice he has for others who have a great idea and want to take it somewhere  

otamotfoods.com

“To grow your business and really grow your experience, you're going to have to work with more and more people.”

“If you want people to be the extension of you, then you've got to give it all for them every single day.”

“I call it being comfortable being uncomfortable. Because if you're going to be squeamish and if you can't kind of thrive off of being in these different and challenging situations and really get excited about, hey, how do I jump over this thing? Then being an entrepreneur or doing something that hasn't been done before is not for you. And that's OK.”

“A little light bulb went off and I said, I love making food, I am a parent that just wishes I didn't have to spend three hours to make this, but I feel really good about her eating it. But is there a life hack here?”

“If we're going to flip the label around, what if we just flip the name around too? And it really plays well into it and really explains the origin of the sauce, which is we really want to turn things around.”

“We prepped enough that well before launch I hired a PR company. Well before launch we did our branding and sell sheets, so we were able to hit the ground running and look like a million bucks before we made any money, before we had one sale.”

“When you're building a business, you also want to look at what will your COGS be later on based on certain velocity assumptions. And you should be pricing yourself based on those future velocity assumptions, in my opinion.”

“If you want to go national, you have to be ready for it. And that just doesn't mean, hey, have a few bucks in the bank. That means be ready from a production standpoint, be ready to service them, be ready to understand how freights work, how UniFi works…”

“If I didn't have great teams on both sides of the table, I could not do this.”

“You just have to be someone that's been used to juggling life and you have to enjoy being that clown.”

• What got Isabelle so interested in the plant based food space and how she has spent her time learning so much about it and seeing the opportunities present in it
• How she came to realize the incredible benefits of Lupini beans and the huge opportunity there was to build a platform and a brand around this bean that many people did not know about yet
• What brought her to the US for one year during her undergrad, took her to grad school in Europe, and got her into the startup space once back in the US
• What valuable lessons she learned from the startups she worked with and how those lessons translate now into how she leads her company and how she values the people on her team
• How the opportunity to run with her idea for Lupii came about and what it took for her to find the perfect Co-Founder
• What the fundraising process has been like and what conventional and unconventional ways they are raising funds to grow the company
• How they changed their strategy once COVID put a pause on their retail relationships and why selling on Amazon has been helpful to them in the early stages of their business
• What advice Isabelle has for getting through the hard times, being a good leader, a good Co-Founder, and also building something bigger than just a business
• What is next for Lupii and where you can find them around the US and online

https://getlupii.com/

“We are using the whole bean, which means that you're getting all the protein and all the fiber and all the minerals without any of the added junk. So that's pretty innovative in this space.”

“It's great to want to take the playbook and tear it apart and throw it out the window. But it's also really important to even know how the playbook was written and you need experienced people for that.”

“I think the trust piece is so essential, especially if you start something new and nobody knows you, and you have to build your reputation, it's important that you create trust and you can only create trust if you listen.”

“It's important to listen and take in information and then make decisions from there, versus thinking you know it all because you don't.”

“Surrounding yourself with a team, with a Co-Founder, that has complementary views is not easy because you tend to want to hire people that are like you. Get people on board that are different, that operate differently, that have different backgrounds, so that you can make informed decisions…”

“Really, the job of the leader is to set everyone else up for success.”

“You need to be open minded and self reflect and understand why am I behaving this way and why is this person behaving that way and how can we find a middle ground and do the best out of both? Because I think that's a great way to build a successful business with complementary skill sets and ways of doing things.”

“What we love about Amazon is the fact that we get exposure to customers who would otherwise not find out about us. And we have had really honest, direct feedback, which is so important for us in the early stages of the business.”

“Lupii is a platform for the Lupini bean. We're not a bar company. We're a Lupini bean company. We really see the bars as the first product range that we launched with.”

“What I've learned is really there are hurdles that will feel tough at times, but then things will always work out if you just continue being committed to it and working at it.”

• What it was like for Achal to grow up in a family of doctors and health care professionals with roots both in India and in the US and how much he learned from being a part of such a family legacy
• How his first jobs were scanning patient charts in order to convert them to digital and then working at Subway as a Sandwich Artist
• What his work at Deloitte was like and why meeting his Co-Founder then created a strong partnership that led to the idea and creation of Cabinet
• What convictions led to Achal and Russ deciding that they could bring about innovation in using sustainable options for packaging and why it is so important to them
• Why batch level testing is so important and a vital part of how Cabinet ensures product quality and safety
• How fundraising has gone and what valuable lessons he has learned along the way, which has led to wonderful financial partnerships
• What great advice Achal has for hiring and maintaining a cohesive company culture, even involving various team members in the hiring process who can help keep the cultural fit clear with new hires
• What routines and mindsets he operates in daily in order to keep himself balanced and work through the highs and lows of being a Co-Founder/CEO and building a company with a great impact
• How he has grown from a Founder into a CEO and why he sees those roles as different with a different set of needs at a different time

CabinetHealth.com 

“My vantage point is, if you build a business, especially in the world of health care, that isn't prioritizing consumers' well-being, then that's directly oppositional to the purpose of being a business.”

“I think our physical health and the environment around us are inextricably linked. And yet in the world of health care, there are no sustainable options today.”

“It's exceptionally complex to innovate in this space. The supply chains are global. They're fragmented. Bringing more sustainable products to market requires regulatory expertise, requires buy-in from your entire supply chain.”

“Being able to call someone who actually believes in you as a person, and not just the business, has been fundamentally important to our well-being and our success over the last few years.”

“Reflect on why you are raising money before you go and raise capital.”

“If you sell a product, it makes money, really think twice about why you're raising and if there are ways that are not just focused on a more heavily equity driven route that could actually enable you to be more successful in the long run.”

“Your goal when you're fundraising is to gain momentum. And so really what you're looking for is not necessarily the check itself immediately, but the commitment that the investor will participate in the round.”

“Don't get too caught up in setting a valuation or in some of the caveats the investors give you. Focus on getting the dollar commitment and you'll find that the rest of those contingencies typically fall away as a round comes together.”

“Being a CEO... I fundamentally have three responsibilities. The first is setting a clear vision for our team and the strategy that goes with that. Secondly, making sure we actually have the right team in place, making sure that they're taken care of... And then third, making sure we don't run out of money or that we're making enough money to support that team.”

“Building this company is my opportunity to continue the legacy of my family in the world of medicine to help people live healthier, happier lives, fundamentally building a more sustainable health care company.”

“When you feel that you don't really care if you're going to hit barriers or failures otherwise and you're going to build that thing, I think that's when you found the correct why for yourself.”

• Why David wanted to create this company with a product that needed to be iterated hundreds and hundreds of times to get it right to be a non-alcoholic alternative that could be added to cocktails 
• What the process of doing what so many people in the industry thought was impossible was like and how they persevered with this unique idea
• What it was like launching a brand right before a pandemic and how they navigated those unusual challenges
• What childhood in Oklahoma was like and what ways David was entrepreneurial very early on, learning valuable lessons about hard work even as a teenager
• How he got into the fitness and physical therapy world and what led him to the CPG world after that
• What advice he has for Co-Founders and for setting yourself up to be able to let go more easily as you scale and grow the company
• What unique route they took for raising money and what advice David has for other founders when looking for non-traditional fundraising ideas
• How David and his Co-Founders run the team and cultivate a company culture that is built on trust and respect and keeping it personal
• What is next for Ritual and why they are confident that Ritual will become synonymous with nonalcoholic spirits

RitualZeroProof.com

“The idea never left. And what came to me was, if we could actually make these taste like known spirits, if we could approximate the flavor profile of whiskey, of gin, tequila, rum, that'd be amazing.”

“The devil's in the details and the details matter. Let's get it right. So we kind of knew we were on to something really early on in the process and it became a matter of perfecting.”

“It's kind of like the Impossible Burger or almond milk. There's never going to be a world where the coffee joints don't sell alternative milks to go with your latte. And in no world, the grocery store is not going to have alternative meats. Now that it's there, people are buying it.” 

“What we've learned is you can't change consumer behavior. They're going to do the thing that they want to do. Maybe it's not real meat, maybe it's not real milk. Maybe it's a Ritual Margarita instead of the real thing.”

“If I could do things differently, it's prepare for more success because this category is on fire. This company is leading the charge in the United States for a category that's really needed. And nobody understood just how big this was going to get when we first started the company.”

“You just can't do it yourself. You certainly can't scale. And if you started off with the mindset of this is mine, mine, mine, it's really hard to give those pieces away and grow. And you have to be able to give things away to be able to grow.”

“There's nothing not personal about a startup. The whole 'It's just business' thing is complete bullshit. It's just personal. Keep it personal and become friends.”

“The most important thing you can have among your Founders and among your employees is trust.”

“It is so very gratifying to build something and see something out in the real world. But I think it's just worth it. I think it's a shame if you don't give some version of entrepreneurship a shot. It's a wonderful way to grow as a person.”

“It's a learning process. Your life is about learning. That's as important as the money you'll get from this, and you'll realize later ultimately more important than the money you'll get from this is how much you've learned, people you've met, the experiences you've had…”

• How Matt got involved with such a unique company and what the process of deciding to jump into this role looked like
• What led to the decision to build the company through drops and why that has been such a great success
• What Matt and the team did to build enough hype to very quickly have enough interest to sell out every weekly drop within 30 minutes or less, sometimes even down to 10 seconds
• Why experience, brand, and then sales is the order of their focus and how being intentional about their brand integrity has brought exponential growth in a very short period of time
• What Matt’s extensive experience as a Founder and marketer in other companies in other industries was like prior to becoming the CEO of Last Crumb
• How fundraising has been unique and why they approached it in a very Last Crumb way that will set them up for further growth and success
• What Matt’s leadership skills are like, what his superpowers are, and why he believes in a lean team that is focused and tight to move forward in efficient ways

lastcrumb.com

“I shared the cookies with other people as I was exploring the opportunity and continued to talk to Derek. The response was exactly the same from everyone, which was, "Oh my God, this maybe is like the best cookie I've ever had.’"

“I think we make a really cool product that makes people really happy because it's just ridiculous.”

“There was a little conspiracy theory going on on Instagram for a while that here's no actual cookies for sale. And these people are just making this up. And it's a total marketing scheme which would have been entertaining and kind of fun. But that wasn't the case. We were increasing production by fifty percent week over week.”

“We are growing ridiculously fast. And our goal is to get cookies into people's hands, but to do it in an ultra premium way.”

“We look at ourselves as the intersection of luxury gifting, fashion, and then CPG.”

“Because people are sharing our cookies, because they have this interesting unboxing and wow factor, I think that in a way it almost creates an experience dining thing that happens with you and the people you're with that you remember and you want again.”

“We had a lot of hypotheses and we tested them. And some of them have worked really well and some of them haven't worked as well. And we're learning and we're continuing to iterate.”

“If you don't think you have it {product market fit}, you don't have it. And I think that's a really interesting thing is that, if you make something really great and it resonates with people and they want it, you know. You don't have to beg them.”

“I think that what I'm finding is that it's happening faster than I would have expected. But we're going about it in a way that is different than I've ever done it. And it's really interesting to see that.”

“Find a really good CEO or people who've been CEO that you can call.”

“My goal is that kitchen ops every day wakes up and says, "I wish you guys could have sold and shipped more cookies because we could have made more. "And every day the logistics ops says, "Man, I wish you guys could have baked more cookies because we could have shipped more." And I think that's a really interesting friction that we want to have.”

“Take the first step. Don't worry about finishing the race. Otherwise, you're never even going to get a chance in the race.”

• How growing up with entrepreneurial parents taught her a lot about hard work and hustle and why she was always interested in creative type careers
• What types of jobs helped her learn how to run a successful business and why her time at eBay was impactful in her experience with marketing, which is helpful today as she has been marketing her own product
• Why tea has always been an important part of Sashee’s life and how that became a pivotal part of becoming a Founder and creating Tea Drops
• What the impetus was for getting her to prove the concept and build her company  on a solid foundation that led to more opportunities
• Why she is thankful she had to bootstrap this business in the beginning and why it helped her make great, strategic decisions early on 
• What struggles Sashee and her team had to overcome in the beginning of building Tea Drops and what struggles still occur now
• What fears she had to overcome, including the fear of public speaking, which she has now conquered and actually been rewarded for great pitches by PepsiCo and Tory Burch
• How she’s grown as a leader and what great advice she has for other Founders and operators who are wanting to build a successful business while maintaining a healthy life/work integration

MyTeaDrop.com

“I got exposed to email marketing, digital marketing, our social giving platform called eBay Giving Works at the time. And so I was exposed to a lot of different facets of marketing and that all was very useful when the time came for me to actually start marketing my own product.”

“Growing up I was always exposed to tea culture and not just from a functional standpoint, that tea is a functional beverage that's good for you, but very much so that tea is this communal beverage that connects you to your culture, connects you to other people and connects you to your family.”

“I loved every aspect of it. I loved the challenge of it. I loved not knowing what was happening next, but really working on something that I felt needed to exist in the world.”

“Don't get me wrong, I was very scared. But I also knew that if I didn't try it now, I would have a sense of regret about it.”

“Everything is nice in theory, but when you actually have to put it into application, practically do it, it's a whole different ball game.”

“What bootstrapping does is it provides you with a certain discipline. You have to make hard choices and you have to do it with your own money.” 

“I grew the brand organically to probably 500K in revenue just from these boutique retailers before I took in capital, and that was really just a function of building a close relationship with the retailer early on.”

“I think the challenge is more so just keeping an eye on what is your end goal and objective and not being so dissuaded or deflated by the feedback that people are naturally going to have, especially with something that's new.”

• How he spent his childhood growing up in China and Spain learning the supply chain and manufacturing industry through his family 
• Why Aaron came to the US for college to study engineering and why he loved the problem solving aspect of what he was learning
• What companies he interned with during his time in college and what he learned about hard work and determination throughout the process
• How his time at GE taught him so much about the processes that would help him scale his own business later 
• Why he started Caraa, what the thesis behind the brand was and still is, and how they began to carry out their mission as a high-end, functional handbag DTC company
• Why he is thankful for a Co-Founder, and what building Caraa was like in the early days of the company
• Why they decided to not be venture backed, what that has looked like, what they have learned, and what advice he offers to others regarding fundraising
• What Caraa has done to help people during the pandemic and why that has been important to Aaron and his Co-Founder, Carmen
• What is next for Caraa and how they will continue with their steady, sustainable growth and intentional customer affinity for years to come

Caraasport.com

“There's always extra things that might not directly tie into hard work and merit, but I would say 90% of the time when you work hard and you put your heart into things, it will pay off.”

“You have to understand the human aspect of people. So having that perspective and having that emotional intelligence was something that I had to learn the hard and quick way.”

“If I aspired to be a CEO or a business owner, having the know-how in terms of process management was very important to me.”

“What we said is, what if we turn things around a little bit, still make the products in a very high end way, but really kind of make it very functional and keep the prices below four hundred dollars in terms of our average order value, because we're going to direct.”

“Stay true to who you are in terms of authenticity.” 

“You'll be surprised if you do a little bit of soul searching, how much you can discover.”

“To a certain extent it helps to have a Co-Founder. You know, I think single founder entities are very tough, not because you're not capable, it's because sometimes you need a shoulder to cry on.”

“I'm a big believer in product market fit. If you can sit somewhere and think about, hey, the world needs these, but if you don't find the right audience to purchase it or to resonate with your product then you just have a little project or a little hobby. It's not a business yet.”

“I was looking to grow, but I was looking to grow sustainably in a profitable way, if you may. So we ended up just saying, you know what? No to venture funding.”

“When we were trying to raise, I felt that I was becoming more and more a professional fundraiser versus a professional business manager.”

“We had that emergency meeting, me, Carmen, and also the board really quickly made a decision to convert part of our factory into essentially making masks using our scrap material. This was in the early days of the pandemic. And then we donated.”

“If you don't have the right processes, everything will be very chaotic. So I think we do a pretty decent job in terms of creating controls and checks and balances and processes along the way.”

“In moments of crisis, in front of the customer: transparency, transparency, transparency. Don't hide anything.”

“Make sure that you have product market fit and then test quick, fail fast, and then reiterate.”

• How Rachel’s big family with two entrepreneurial parents provided the opportunity to grow up learning about business by watching her parents lead.
• How she built her confidence in college in order to build and lead a successful company.
• Why her time working at American Express and Gilt Group helped her learn valuable lessons from both a big company and a small business that gave her a scope to be set up to scale Daily Harvest successfully.
• How her observations about her work and eating habits led to her investigation of the food industry and to creating healthy, convenient options. 
• The metrics Rachel set in the testing phase to see if she had a product market fit and how Daily Harvest took off so quickly.
• What it has been like to create and scale something that had not yet been done before, what lessons were learned the hard way, and why they are stronger now than ever before.
• Advice she has for building, growing, and communicating well with your team as you scale and why it is so important to have an open dialogue from the beginning.
• How her unique and steady approach to fundraising led to being able to partner with value-aligned investors who have been a good fit and have helped her in her goal for consistent capital efficiency.
• How she has grown as a leader and continues to grow as the business grows, and what is next for Daily Harvest.

DailyHarvest.com

“As a child, my parents were so passionate about what they were doing, and I could see it.”

“The box that I actually needed to check was the confidence box, not the education box or not the work experience box.”

“Seeing what happens when things aren't going so well and how some of that could have been avoided by more disciplined growth really led me to focus on things like capital efficiency when starting Daily Harvest from day one.”

“When I think about how I've built Daily Harvest, and what our goals are, and how we treat our people, and how we invest in talent and growth and management skills, I think a lot of it is informed from that incredible environment that was created at Gilt in the talent incubator.”

“I started looking at the food options out there and trying to figure out why they were the way that they were. And for me, it really comes down to how they are structured, number one, and how they view success in the public markets.” 

“If you think about what slow, steady growth and dividends mean for food, something that you ingest, there's a lot of squeezing margins. And when you think about squeezing margins out of food, it's also squeezing nutrition out of food.”

“I set a metric for myself, which was very important for me, because what I wanted to avoid in this little MVP experiment of mine was I like to call it the Girl Scout cookie effect or the wrapping paper effect... I wanted to make absolutely sure that there was no ‘my friends are feeling bad for me’ effect.”

“Economies thrive with specialization. And so do companies.” 

“You need to hire experts in certain areas, and it can create this really uncomfortable situation with those early people who you owe everything to, but it becomes murky when there's not a clear path for them. So my advice to people is to just have that awkward conversation up front and to have it frequently throughout the growth stage.”

“Early on I felt like, "Oh, I'm a founder now. I need to have this morning routine and I need to have work/life balance, and I need to have all these things." Like that was stressing me out more than just being like "I'm at the center of a tornado, and it's great.’" 

“I think going from down and in to up and out was kind of the hardest transition because it's not just something you can do yourself. You also have to make sure that you have the right team to be able to support it and you have the right accountability that strings through the organization. And those things are hard to orchestrate.”

“You want people who look different, who think different, who have different experiences that they bring to the table, but it's so important that the values are aligned.”

• How her love for food was a part of her family culture and why she originally thought she’d pursue medicine or law
• How New York City changed her perspective on what was possible and what her many internships taught her during her time at NYU
• Why she pivoted into the tech industry and then took some time in the venture space, learning a lot about startups, venture capital, the ups and downs involved with building a brand, and that she loved being an operator
• What brought her to her next step, the creation of Brightland, after olive oil became a pain point in her own household
• Why she decided to bootstrap first, what her experience with fundraising was, and what advice she has for other founders when it comes to raising
• What team building has been like for Brightland and what lessons Aishwarya has learned in building her team and building her brand
• What advice she has for aspiring entrepreneurs and what is new and exciting for Brightland

Brightland.co

“I went to a venture firm, spent some time there, but realized that I actually love operating. I love being in the weeds of a company and being a part of that growth rather than sitting on the sidelines.”

“Eventually I took my own just digging into why I had this fear or kind of working it through with my own inner critics. It was a lot of deep work that I had to do to then be like, you know what? I am going to try this and do this.”

“People are discovering brands and entities on their phones and people's attention span is two seconds. So I think that it is important to have, if you can, something that's striking, that is memorable, and that then usually means that there's a design aspect to it.”

“It's a numbers game. You have to talk to a lot of people. And it's tiring because it's taking up time that you're like, oh, well, I could be furthering the business or doing something to push the envelope or push the ball forward. But then when you meet the people that make sense for you, then it clicks into place.”

“Always having a mindset of abundance over scarcity... If you're playing the scarcity game and feeling that, then the person on the other side can feel it, too.”

“I think we also have the luxury because we are a small team and I'm building this with a lot of intentionality and not just trying to like blitz scale it in any way, so we have capacity to be a bit more thoughtful about who we're bringing on.”

“If wellness and what you're kind of ingesting can be considered beauty, then our product certainly can be."

“Your website is basically your storefront, so really understand the story that you want to tell. The more personal you can tell, the greater resonance and customer loyalty you'll build.”

“When you feel like you're getting overwhelmed, just take one step forward at a time rather than looking at the big picture.”

“Your team is everything, and you are nothing without them and being able to recognize that and celebrate them and be able to understand. Empathy is important for everything.”