Danielle Tate, Founder and CEO of MissNowMrs, talks with host Justin Gray about missing medical school by three spots, leaving behind her successful career in sales and what it’s like being a pioneer in the wedding tech space –– all on the the latest episode of Driven: How Did I Get Here?

What do you do in your current role?

MissNowMrs is an online name change service for brides. We condense the tedious 13-hour process of collecting all of your forms of identification, going to all the government offices, and filing for your new name into 30 minutes for $30. We're many years in and just crossed the 370,000 customer mark. Nothing's the same day-to-day which is something I very much enjoy as an entrepreneur. I'm forever making new partnerships, building new brand platforms and extensions to continue to grow and scale in a way that keeps me busy and happy.

What did you want to be when you grew up?

I spent the first 20 years of my life doing everything possible to become a cardiologist. I spent a summer at an internship at Ohio State University Heart and Lung Institute. All I did was help with heart catheterizations and watched open-heart surgery and I just fell in love with all of it. I made all of the hard choices, took all of the hard classes, all to miss med school by three chairs. It was definitely a low.

When you got this news, what were your options?

My parents thought that I should move home to my very small town in Pennsylvania and work for the local physician and reapply. I couldn't imagine moving home as a failure. I ended up selling copiers. I learned that I love selling things but I just absolutely hate selling copiers. I parlayed that into a position as the number one sales rep for a very large medical diagnostic equipment company.

How did you make the jump from being a quota carrying sales individual to forming your own business?

I was very careful about it which is probably not something you hear from entrepreneurs. I had the idea and I didn't immediately quit my job. I did some research and turns out there's 2.3 million marriages a year just in the U.S. and 88% of women still change their name. That was a big renewable market. I starting doing research on evenings and weekends and dual tracking for a number of months, but I was also driving 1,300 miles a week for my job. At a certain point I knew one of these had to get my full attention or I'd do poorly at both. I ended up quitting my job and within 30 minutes of turning the website on we had our first customer. Within the first month we were profitable and we never looked back.

What has it been like being a female entrepreneur and being under what is typically thought of as a glass ceiling?

I don't think that there's a glass ceiling per se in entrepreneurship. There's more of a sticky floor. Women can think of every reason why we shouldn't be entrepreneurs. Why the company would fail. Why someone else would be better at starting it then we would be. Then there are statistics showing we have 35% higher return investment than our male entrepreneur peers.

I really feel like we're at the tipping point for women’s entrepreneurship - there are suddenly enough women entrepreneurs that there's room for people to mentor. Now women are exiting and investing in other women's companies. That's a very key point in the ecosystem.

You wrote a book titled Elegant Entrepreneur: The Female Founders Guide to Starting and Growing Your First Company. What are some lessons you’re imparting through the book?

It's literally everything I wish I had known. Here's how you do it. The end of each chapter is a list of real, tangible resources you can use if you're living that particular step. My favorite part is each chapter ends with how it feels. I think if I could have known emotionally what was coming down the pike I could have prepared myself and been a little bit more successful faster.

Connect with Danielle Tate at missnowmrs.com, LinkedIn and Instagram.

Marc Chesley, President of OfferPad, talks with host Justin Gray about practicing law, flipping homes and helping grow Infusionsoft into a $100M company –– all on the the latest episode of Driven: How Did I Get Here? 

What are you working on these days?

At OfferPad, our purpose is to revolutionize the way homes are sold. We have the technology platform where you can go to OfferPad.com, put in the address of your home and within 24 hours you will get a very strong, very fair, purchase offer, where OfferPad is the buyer. We're solving the pain, uncertainty and worry that usually comes with the traditional model of selling and buying residential real estate.

What did you want to be when you grew up?

I wanted to be an entrepreneur. My grandparents were great entrepreneurs. My grandpa Tilby started up JT Aviation and built one of the largest private hangars in the Northwest. My other grandpa, Earl Chesley, owned Chesley Well Drilling. It inspired me, as a young boy, to watch my family, so I think that’s where the foundations of my entrepreneurship journey may have started.

What was your first job after earning a law degree?

I wanted to have some trial time, so I volunteered for a bunch of unsexy cases. I did a bunch of M&A, veteran capital and private equity financing, but the court room stuff I did was mostly real estate-based. Then I got recruited out of the firm by a tech company called Wind Force Technologies, which was a great startup tech company that rebuilt case management software for big legal cases. It was a great blend of my legal training and my technology passion. That's really where I cut my teeth in software development, product development, user experience and design, solving problems for customers. 

How did your path to entrepreneurship and technology converge?

From Wind Force Technologies I helped start up another company called IP Partners. While I was helping those guys, I started flipping houses on the side. In 2004, I flipped about 56 houses. Later, I could tell that the rate of appreciation was unsustainable and I wanted to get back into tech so I liquidated everything. Looking back, it was perfect timing in 2005 because it helped me be one of the first investors and get Infusionsoft up on its feet. I did my part and had some fingerprints on Infusionsoft through the next decade until I left the company at the end of 2015. So over 10 years I helped grow it from startup to over a hundred million a year.

Have any mentors played an important role in shaping who you are?

There's a great book called The E-Myth by Michael Gerber, and in the early days that was one of our manuals. One of the co-founders at Infusionsoft, Scott Martino, and I went to a seminar that Michael was holding that was a hot seat format. He got us up there on the stage and was really was grilling us: What is the meaning? What's the purpose? Why are you doing this? The world needs somebody to really carry the torch for small business. He started talking to us in terms of, “Hey, the world needs this” rather that “this is a good opportunity and you’re going to have a good exit one day.” He emphasized this was our responsibility and we had a duty to help small businesses succeed. That really touched us in a profound way.

What are the traits you look for when hiring?

I look for five things in an A-player candidate. They have to be a solid core values fit. They have to have a high "give a damn" for the target customer. They have to be smart, hardworking and be a good team player.

To find out more about the BHAG (Big Hairy Audacious Goal) Marc has planned for OfferPad in 2017, click here to listen. Plus, visit Offerpad.com and find Marc on LinkedIn.

Nate Martin, Co-founder and CEO of PuzzleBreak, talks with host Justin Gray about his childhood dream to make video games, lessons learned from his first startup and advice for people considering entrepreneurship –– all on the the latest episode of Driven: How Did I Get Here?  

Can you explain the escape-the-room concept?

At a high level, these are rooms where groups of players - friends, family, strangers or co-workers - are trapped. They have a set amount of time, usually an hour, to work together to find hidden clues and solve puzzles to unravel a mystery and escape that room before time runs out.  

When you were a kid, what did you want to be when you grew up?

The only thing I ever wanted to do was make video games.

There's a huge market for that. Did that come to the light of day?

I actually went to the DigiPen Institute of Technology, which had a focus on making video games. After that, I went to work for Microsoft. Over my seven years I got promoted a number of times, but was still eight levels away from the CEO. If ever wanted to become a C-level executive, I was going to have to live to be about 250 years old. I realized that if I really wanted to be master of my own destiny and take the helm of my own enterprise, I would have to do it myself.

What came next?

After Microsoft, I was an executive at Electronic Arts, which was actually a video game company. This was in 2013. A bit of context: the escape-the-room concept was originally almost a genre of video game. So purely by coincidence, one day my future co-founder and I discovered that people were doing this in real life. She was living in Seattle and I had spent many years in Seattle and it was like, "We have to do this in Seattle. This would be a huge hit."

Puzzle Break is not your first entrepreneurial adventure, correct?

I had another startup for about 10 minutes. We made every mistake you can make, but it was an explosion of learning. It's worth mentioning I can't point to a product or service that's running today that came of my 10 minutes there.

If you could rewind and give yourself advice at the beginning of your career, what would you tell yourself?

Probably the most actionable information that I would tell myself as soon as I leapt into the entrepreneurial arena, is just, "Ready. Fire. Aim." Don't spend too much time in the proverbial basement creating what you think people want until you can actually talk to them with a product in hand.

Do you have advice for someone considering doing something on their own?

There's a lot of awesome stuff about running your own business and figuring it out as you go. But there is a lot of stuff about having a reliable and nice day job that a lot of folks take for granted. There's a lot you miss when you become an entrepreneur, from the safety net to the hours, to the social thing. Also, if you’re an entrepreneur who is having some success but you're hating life and you're hating this lifestyle, there's no shame in figuring out you only want a side-hustle and that's it. In other words, don't assume that the famous entrepreneurial stories out there are nothing but roses. Because I can assure you that they are not.

Tell us about what a day-to-day looks like for you?

I typically get 400 emails a day, so I usually try to get through the important ones first thing in the morning. I have a daughter, so once I get her off to school I try to keep meetings more toward the middle of the day. I like to have enough time to start on action items. It drives me crazy to have too many balls up in the air. I’m happier if I can finish some things and give closure to issues.

You own 56 Subway restaurants. How do you manage that volume of stores?

You have to find good people and delegate the proper accountabilities to them. I have 600 employees that rely upon me to make sure their paychecks are good every two weeks, so there really isn’t such a thing as a day off. Day in and day out there’s always work to do.  

What did you want to be when you grew up?

My father was a patent attorney for a major manufacturing firm. I never really thought about it much, and just assumed I would also be an attorney. Then I woke up at 18 and decided to go into journalism instead. I ended up switching to marketing when I realized my journalistic dream wasn’t going to pay anything at all. I thought marketing would be my ticket to getting a good job with a good company and making a good salary.

What made you change your direction?

Right when I was about to graduate my father died. I started to wonder if I really wanted to chase all those things. I decided I would go back to school and pursue elementary education and possibly become a coach. I thought education would be more meaningful than selling widgets.

How did your father inspire your path to entrepreneurship?

The last time I saw him he said if he had one dream in life it would be for me and my brother to be able to own our own businesses. Owning a business was something he’d always hoped for himself, but by the time he was 32 he had four kids and a wife and didn’t feel he could take the risk. He passed away five months after this conversation and it really stuck with me. A year later the Subway opportunity came along. Subway was not a young company in terms of years, but it was in its infancy in terms of the number of restaurants that were around. At the time there were about 1,400 Subway restaurants. Today there are more than 40,000.

What made the opportunity for Subway so attractive that you wanted to dive in head first?

From my perspective, running a business is like teaching and coaching, which is exactly what I wanted to do but through a different platform. Plus, I was partially motivated to take advantage of the opportunity because it was my dad’s dream. I figured at some point you’ve got to jump in and take a shot. It was scary, but I believed in my efforts and that I’d work hard.

What do you hope for your daughter in her career? Has she caught the entrepreneurial bug as well?

She wants to take the business someday! I hope she does something I’ve never thought of. If she wanted to be a manager of a Hilton Hotel in outer space, I’d be excited for her. I tell her to chase her passion. If you figure out your passion, then that’s always what you should chase.

What are some of the characteristics you look for in a good hire?

Yes, we’re in food service. But realistically, we are in the people business and are serving food. We aim to find people who are outgoing and personable and empathetic. It’s about great guest service and quality food. To find the right people you have to ask the right questions in the interview. If you just ask, “Why do you want the job?” or “Will you work hard?”, you won’t always get the answers.

Do you have a favorite interview question?

My favorite question is a two part question. I think everyone has a point in their life where things go very well - for whatever reasons it’s the best time of their life. And conversely, there’s time that doesn’t go well at all. Talking about those two things, you can tell who is able to open up and make connections with other people and listen and ask the right questions. We can give average service all day long, but what it really comes down to is outstanding customer service. And in order to do that you have to have the right people.

Jenny Poon, founder of CO+HOOTS, CO+HOOTS Foundation and eeko studio, talks with host Justin Gray about her dream of becoming an inventor, her foray into the corporate world and how she ended up a serial entrepreneur.

What does a normal day look like in the life of Jenny Poon?

My days are crazy because I run CO+HOOTS, CO+HOOTS Foundation and eeko studio! And I have a two-and-a-half-year-old daughter. So normally I get up early for breakfast and then I’m on email and getting on track for the day. I schedule my days around when I’m most productive. Meetings are for the mornings and afternoons are for when I’m working by myself. As much as I love a coworking space, when you’re the owner of one, you can’t get much done when there.

What did you want to be when you grew up?

I dreamed of being an inventor. It started in third or fourth grade when we had to create these little machines with various items (like a spoon) to accomplish certain goals. I loved creating solutions for everyday problems. When I was younger I used to share a room with my brother and sister, and we would always fight over who had to turn off the lights. I ended up stringing a rope to the light switch and attached it to the ceiling and strung it across the bed so I could easily flip the switch. There ended up being a lot of strings and contraptions in our house. Really, I craved the moment of finding a solution that worked.

How did the seed get planted to become an entrepreneur?

My parents are immigrants and came here with nothing, but were fortunate enough to be sponsored by a family in Minnesota who helped them with housing. Somehow, they started a restaurant in Minneapolis. It’s always just been my parents running it and then us three kids helping out. As an adult now I see it as such a blessing to have seen firsthand people putting in so much hard work for something they really loved. What I learned was you can have a family and build a business and succeed. It’s possible but you do make sacrifices. 

What did you have in mind when you went to college?

After growing up in the restaurant, I knew I didn’t want to end up working 24/7. I thought it would be so great to have a cushy job where someone paid me and I got benefits and vacation time, so that’s what I was looking for. I studied journalism, advertising and graphic design. I eventually worked my way up to these jobs in corporate America, and realized it wasn’t for me after all.

What were the indicators corporate life wasn’t for you?

I was working at the Arizona Republic, which is a great newspaper, and had been named the new art director for a magazine they had. On the second or third day they pulled the team into a meeting and explained how they wanted us to succeed and asked what could they do to support our efforts. When it was my turn I suggested creating a website or even a landing page, but was told basically the Internet was a fad and my efforts would be better focused on other things. Wow, that was a big signal to me! I knew then that there was a big barrier and it wasn’t okay with me. I ended up starting eeko while in that position and finding I loved being the director my future.

What was the catalyst to your coworking space?

I’m an introvert so working out of my own space on eeko was great! But I realized at one point I was in my home office and it was 4am and I hadn’t been out of my house in two days. I started thinking about what would be best for me, and I realized I loved being around teams and seeing other people be amazing. It makes me inspired and want to kick ass. I needed it.

So I went out looking for a place to house me and my team but I wanted to be smart about it after hearing about companies that worked basically to pay their rent. I knew a bunch of people either working on their own or growing their small businesses and saw the opportunity for collaboration. I ended up finding the perfect place but it was 10x too big, so that’s when I looked into having other people join me. 

As you look back, what were the most important characteristics you’d look for in a business partner or hire?

My husband is my best business partner because we’ve failed in the past enough to know how to make it work in the future. A lot of it comes down to communication style. I have failed with other partnerships. Sometimes there are people you don’t work well with. You can only control the things you control yourself.

To connect with Jenny, visit www.cohoots.com, email her at [email protected] or find her on Twitter.

Greg Head, strategic growth advisor, speaker and writer, talks with host Justin Gray about how he got his start in the software business, qualities he looks for when connecting with early stage founders and what every entrepreneur should know as they prepare for growth –– all on the the latest episode of Driven: How Did I Get Here?

What are you involved with right now?

After 30 years in the software business, I’m now advising CEOs of growing companies and consulting when they get stuck in their growth phases. These are typically CEOs of companies in the $1M - $10M range.

Let’s go back to the beginning. What did you want to be when you grew up?

I wasn’t sure, and I think in high school I didn’t want to grow up at all. I was an undeclared major at the University of Iowa for a couple years until I fell in love with business and economics. I wasn’t sure about software or being in sales and marketing or even what it meant to help grow companies. In some ways, 30 years ago it was only the misfits who got in the software business.

What happened after college?

After college I headed to Chicago to look for a “real” job. A friend of mine invited me to work at this retail store called Egghead Software, which was one of the fastest growing companies in America at the time. ACT! had just been created and most salespeople didn’t even use computers at that time; they had shoeboxes of business cards. But a few salespeople were starting to use software and discovered they could sell more because they used software like ACT!.

At the time, ACT! and companies like Microsoft and Intuit used to send their employees to the Egghead stores to do demo days. And all of a sudden there was one Egghead store that was selling 10x more ACT! than anybody else. It was because I had taken it under my wing and taught everyone how to sell it, so I came up on their radar.

Everybody in my family was waiting for me to get a real job, and then I joined this scrappy software company at a time when everyone thought salespeople would never use software. But, 30 years later, salespeople definitely do use software. That’s where opportunities are - getting in early when it looks crazy and then it becomes obvious years later.

Is there something definitive you can point to that successful organizations had during the growth phase that failed startups didn’t have, other than money?

Money is a reflection of it, not the cause of it. There’s a myth you have to be the smartest person with the biggest degree and have the most money, but really who finds success is someone who really cares, thinks big and never lets go of the dream. It’s the people who can overcome the 100 things that would kill most other companies in their growth path. People underestimate the tenaciousness it takes to scale a company. There’s a science to it but it’s not rocket science.

Is there one piece of advice you typically share with CEOs?

It’s way harder than you think it’s going to be so don’t give up when you bump your head a few times. Also, I talk to them about the focus challenge. Many small companies are many things for many people as they get up and running and try to survive. But people don’t want many things - they want the best thing for them. So companies that go through a growth spur tend to go through a phase of narrowing so the world hears them and they can execute best. I compare it to Chipotle owning the burrito.

Tell us about Gregslist?

Gregslist started from me just being out and meeting people in the software community in the Valley. One day I looked at my notes and realized there must have been over 100 based here. People didn’t believe there were so many. So I published a list of 129 SaaS platform and app companies to my website two months ago. Now there’s 230 on the list because I update it weekly and keep finding out about more companies that are here. They make up 20,000 jobs in Arizona, half a billion in funding that’s been visible. There’s just a ton going on. So far 10,000 people have visited the page and now they can click on links for jobs, investors know where to find software companies and founders know where to connect with each other. I recently made a map so people can know who’s next to them so they can make connections and come together.

To connect with Greg Head, connect on www.greghead.com, LinkedIn or Twitter.

What is your current job?

I’m a serial entrepreneur and venture investor. I came up through the tech space and a number of different startups, and have gone through several acquisitions. I leverage the money I was blessed with from there to now invest in early stage ideas. I’m always looking for the next great idea that is at the seed or angel phase where I can help through my own investment or coordinating investments.

Let’s rewind - what did you want to be when you grew up?

I went to my guidance counselor’s office back in high school and they asked me the same question! I said I wasn’t sure, but I know I don’t want to wear a suit every single day. Little did we know at that time the technology explosion was just around the corner. When I was a kid, I wanted to be an astronaut. I was inspired by the space shuttle program and it really spoke to my imagination that anything could be possible. I got into discovering computers in the 1980s. My first computer was an Atari 2700, and it hooked me into all that was possible with computers.

At what point in your career path did you start to hone in on what you’re doing now?

Through fits and starts. In high school I wrote an inventory program for a company and ran it on an early network system, which was a big deal at the time. Then I went to college for a few years. I had been playing beach volleyball, so I actually jumped out and played semi professional beach volleyball on the AVP tour for about five years. Then I realized, this is a fun lifestyle, but I’m not going to make money doing this. So I jumped back into technology in the mid-90s as the internet bubble started to rise and focused my career on virtualization in the early Citrix days. I was part of a company that was acquired by a service provider –– basically a cloud provider before it was called cloud. Before I could cash that check the bubble burst, so easy come, easy go, right? But to make a long story short, it opened my eyes that building companies, making them worth something and selling them can be quite lucrative. So I started to investigate how to do that. And now I get to do my favorite thing, which is to effect meaningful change.

Where did you go to learn how venture-backed businesses work?

I had a crash course in the basics by mentors and executives from companies I was with. And I read as much as I could. Today, you have Shark Tank and everyone seems to be wanting to jump into this game. People can go online for great resources and talks, but remember there’s an art to understanding what these deals actually mean. There’s one really good blog series by David Skok out of Harvard iLab I highly recommend. I did a video for Harvard iLab called, “The Business of the Internet of Things.” I did it to set an example of how I actually approach building businesses. Now it’s the third highest video for Harvard’s iLab in viewership. My advice for others is to just start reading.

What are keys to finding great mentorship?

You can look at mentorship in two ways, first as an outside source to give you information and knowledge. But another way is to look at it in a semi-political way, choosing someone who you can bounce only certain ideas off. I view a true mentor as someone you can ask any questions and there’s trust so you don’t worry you’ll feel stupid, that way you could get real answers back. Finding a network of mentors is important. You don’t want just someone with book knowledge, you want real world experiences.

What was the most important thing you learned at the beginning stage of your career? What allowed you to really parlay this experience and move on to the next level?

I knew after the first acquisition I went through that I wanted to be in that situation again because I realized taking a paycheck is awesome but if you wanted to create wealth, then it’s through markers of ownership. I always balance my deals with cash and equity, because equity is going to be the thing that gets you to the larger wire transfer day that will allow you to compound that into other investments.

What’s your favorite interview question?

The best question is to ask what drives them. It’s a question that shows your true self and what fulfills you as you’re going through your work. If work isn’t fulfilling, then it becomes something that you grind through and you may not love. Understanding what truly drives someone will tell you a lot about that person.

To contact Chad, find him on LinkedIn, connect with him on Twitter at @cloudjones or email him at [email protected].

Marcus Sheridan, president at The Sales Lion and partner at River Pools and Spas joins host Justin Gray in this episode of Driven: How Did I Get Here?”.

What did you want to be when you grew up?

I wanted to be a football coach. When I got to college I wanted to be a gym teacher.  I realized if I was going to support my family, that salary probably wouldn’t cut it. So I ended up majoring in Spanish and minoring in physical education. After college, I went home where I grew up and where two of my buddies had opened a pool company. To make a long story short, I became a third partner in the company and it became River Pools. No one ever says they want to be a pool guy, but that’s exactly what I ended up becoming. 

What’s the background of River Pools?

We started the company in 2001. Things were going okay until the market collapsed in 2008. There was a period in early 2009 where we were all overdrawn on our accounts. We had 16 employees that were just sitting around. We met with business consultants who told us to file for bankruptcy. And so, in an effort to generate more traffic and sales, we knew we needed to throw a Hail Mary. I started to learn about inbound marketing from HubSpot –– looking into digital marketing, blogging and so on. I realized, if you’re willing to hear the questions people are asking out there and you’re willing to address them on your site through text and video, you just might be successful.

We decided to become the Wikipedia of the pool space and we became the go-to experts of fiberglass swimming pools. Our adage became, “They ask, you answer.” It saved our business. Today we get 600,000 visitors a month to our website –– it’s the most trafficked pool website in the world. We became the largest builder of fiberglass pools in the U.S., and now we’re manufacturing pools as well and developing deals.

How long did it take to start seeing results for your business?

At first people started to comment, “You have a really good website.” Within three to six months I could definitively see the uptick in traffic and leads. After the first couple years, I could identify definitive ties between content consumed and sales closing rates. I could see that when people would read 30 pages or more from our site, we could close 80% of the time. If it was less than 30 pages, we’d be closing 25% of the time. I came to understand it was about trust. The companies who are obsessed with gaining trust in their customers, they are the ones who are changing the game. Fundamentally we are trying to just answer what customers ask. I know there are distractions out there, but people are not too busy to take the time to read, especially when it comes to deciding how to spend their money.

Do you find there are certain types of content that build trust?

Yes, I call them the “big five” because there are five pieces of content that move economies. It doesn’t matter whether it’s B2B or B2C, these are the five to consider:

• Cost based questions. Essentially answering the questions like how much does it cost, average price ranges, salaries.
• Problem questions. People want to know what they don’t know about a product. Will this product blowup in their face?
• Comparison questions. This is highlighting honestly the pros and cons of products. Basically the this versus that
• People want to know about reviews of products and services.
• Best questions. People like to search to find out the “best” of whatever they’re searching for. No one searches, “What is the worst Mexican restaurant in NYC.” No matter what the search is about, they want to know what the best is. This, by the way, doesn’t mean they’re looking to buy what the best is. It just means they want to know what it is.

If you had to hire someone to replace yourself, what traits would you look for?

The number one trait I would look for in anyone today is the ability to communicate.

What is your favorite interview question to identify that trait?

First you find out what interests them. Then I ask, “Tell me about that.” It’s a really powerful phrase. There’s a group of people who don’t respond clearly, because they’re not good teachers and they understand all these things that you do not. It’s the curse of knowledge. Then there are other people that will literally walk you through things. And by the time they’re done explaining this interest they have, you feel like you can see it or you’re a part of it. It’s the same type of person who, when they tell you about their vacation, it’s like you were there too. That’s the type of person I’m looking for. That’s the one skill that I have, whatever I am in terms of success, that is far and away the most important skill I have.

To connect with Marcus Sheridan, check out The Mad Marketing podcast and The Hubcast podcast for Hubspotters. Visit his website TheSalesLion.com. Email him at [email protected].

What does BrightWave do? And what do you do for the company?

BrightWave is a very focused digital agency concentrating on email and CRM for leading enterprise brands like Chick-fil-A, Equifax, Mattress Firm, Panera Bread and other leading brands. We manage and advise on email and CRM programs to drive stronger relationships and greater revenue.

I’m very excited to have I hired Raj Choudhury as President about six months ago. It has dramatically changed my focus as opposed to how I’ve been spending the previous 12 months. Before, I was spread very thin and not able to really go deep on a lot of things that were important. Now I’m much more focused on external planning, corporate development, business development, marketing, partnerships – a lot of things that have probably been underserved over the last 24 months or so. I’ve turned over a lot of the internal operations to Raj. My day to day still varies greatly, but I’m really much more focused on the external things and letting him handle the majority of the internal side.

That’s a pretty critical inflection point and one that a lot of founders struggle with. Did you just get to the point where you said, “I am being spread too thin, I can’t focus on anything that really goes deep? And I need to make this change?” Or was it something that the organization came together and made as a group decision?

There wasn’t necessarily a straight line to the decision. It was more that I knew that in the last year that I needed some help and some advice. Raj was a guy that I already knew, and he was available as a consultant. It allowed me to put the focus on cherry picking a smart candidate who has a lot of agency experience and have him just spend 15-20 hours for a couple of months helping me out. From there, I’d figure out what I need to do. Then, when we realized that we worked really well together and it was a very good fit, we quickly tried to figure out how to bring him on in a more formal, full-time role. It wasn’t something that I would have probably pursued aggressively outside, it was more opportunistic.

I noticed some of the stats on your website, including the Inc. 5000 for five years in a row - which is no small feat. You’ve also mentioned BrightWave has been around for 12 years. In the world of digital marketing and email marketing that is quite a length of time! Congratulations on the longevity!

Let’s take a huge rewind and dive into what you wanted to be when you grew up?

A professional baseball or basketball player. I went strong with that. But in about 7th or 8th grade I realized that might not happen.

When did things change?

I wasn’t somebody that was necessarily thinking that far ahead. I was a history major in college. I was somebody that wanted to get a lot of different experiences and exposure in life, but didn’t have a clear path. I knew more about what I didn’t want to do.

My father was in financial services with Morgan Stanley for 30 years.  I did an internship one summer there and realized that it wasn’t a great fit for me. I also interned at the White House. Politics was something that was the closest thing to what I thought would be an interesting path. I grew up in Maryland – close to D.C., so that was intriguing. After I worked at the White House I realized this is a great thing to do for a couple of months, but not a career. So that helped me a lot. Being a history major basically meant that I was unemployed when I graduated. I learned more on the path of what I didn’t like than what I did like until the dot com era in the late 90s happened. Once I saw that emerging, I was all over that and sprinted to it as fast as I could.

For more about how Simms’ path to entrepreneurship and tune in to the podcast. Connect with Simms on Twitter at @SimmsJenkins.

Two powerhouse content marketers –– Joe Pulizzi and Jason Miller ––join host Justin Gray in this episode of “Driven: How Did I Get Here?” podcast. Joe Pulizzi is the founder of Content Marketing Institute, author of Content Inc, and a speaker and entrepreneur. Jason Miller is the global content marketing leader for Linkedin, best selling author, and rock and roll photographer.

What did you want to be when you grew up and how did that lead you here today?

Joe: I wanted to be a farmer actually. I loved growing things, and I actually tried my hand at farming, and nothing grew, so I said “I’m not very good at this farming thing.” I better try something else. I grew up around entrepreneurs. Regardless of what I was doing, I knew that I wanted to be my own boss, and it took me a while to figure out what my tilt would be.

Jason: I wanted to be a rock n’ roll bass player. At no point did I say I wanted to be a good marketer, I can tell you that for sure.

What about being an entrepreneur was attractive to you?

Joe: Honestly, I liked the idea of doing something different every day, and being in all aspects of the business. You’re in control of your own destiny from a day-to-day standpoint.

What advice would you give to your younger self if you had all the experience you have today?

Jason: When I was in the music business, I probably stopped learning for those 12 years, so never stop learning. Learn a foreign language, and get really good at it, and never stop writing. I feel like I’m constantly trying to catch up and be a better person, a better marketer, a better writer, a better father. I love writing, I love helping people and solving problems and taking very complex situations. I just wish I had started earlier. So, never stop learning, keep progressing, and keep that determination going. 

How important is writing for anyone’s success these days? Can you be a successful entrepreneur and not write?

Joe: I know you can, there’s no one formula to getting there. If you look at any of the entrepreneurial books, it’s done a million different ways, but maybe the easiest way to do it today is to write or create content and build an audience consistently over time. Once you have an audience that knows, likes, and trusts you, over time you can monetize that. I don’t care what industry you’re in, you can monetize it. There’s never been a greater time for entrepreneurs than right now. You just have to cut through the clutter.

Jason: In the early days of Marketo, they wrote their first blog before they wrote their first line of code. They built that leadership, then they built a product, and I think it speaks for itself where John and Phil took that company. Good writing is hard, and I think that pushes people away in this era of short attention spans. If you have the passion, and you can write well, in marketing, the rest of the stuff will just be learned.

What is your favorite interview question?

Joe: “Do you know what your goals are? When you get up in the morning, what are you trying to accomplish?” I’m looking for career goals, individual goals, family goals. Are they written down? If you want to see what successful people look like, they wake up in the morning and have a mission. Really understand what you want, and first thing in the morning, decide what you are going to do so you won’t get distracted.

Jason: I ask, “Are you a writer?” Maybe it’s not writing long form content, but you are a copywriter or you are writing social media updates. The second part of that is, “Who do you look up to? Who are your mentors? Who is your inspiration?” If you would’ve asked me that five years ago, many of them would be the same answers they are today. If you don’t have a mentor, or somebody that inspires you that’s in the business that you want to be in, then I’m a little bit hesitant to carry on that conversation.

For more about how Joe and Jason have developed themselves as entrepreneurs and used content marketing as their gateway, tune in to the podcast.

Connect with Joe and Jason on Twitter at @JoePulizzi and @JasonMillerCA.