Editor’s note: This is part of a series of interviews from WRAL TechWire featuring “Legends – The men and women who helped create and build North Carolina’s technology and life science ecosystem.”  These leaders will join Jim Goodnight, Monica Doss, Dennis Daugherty, Charles Hamner and Venessa Harrison as members of WRAL TechWire’s virtual Hall of Fame, which named its first members in 2017.

David Gardner is a serial entrepreneur, writer, adviser, and manager of early stage investment fund, Cofounders Capital. He has more than thirty years of experience in creating and building software technology companies. But in college and graduate school, he studied music, theology, philosophy and dead languages, which oddly enough, led to his career as an entrepreneur.

Gardner, who paid his way through theology school playing piano in bars, recently sang a song he wrote for his daughter when she was seven at her wedding.

David Gardner, General Partner, Cofounderes Capital. Cofounders photo.

After failing at retirement twice, Gardner became one of the Triangle’s most active angel investors spending his time as a volunteer coach and mentor to startup founders and managing a free accelerator he sponsors with the Town of Cary. To combat the lack of early stage capital in NC, David created and runs Cofounders Capital, a $12 million seed fund, the success of which led to a second $31 million fund.

As an entrepreneur, David was the founder or co-founder of seven companies including PeopleClick (purchased for $100 million) and Report2Web, which sold for $12M in less than eleven months from inception. He has demonstrated a record for consistency across multiple industries with six successful exits in a row… and one he refuses to talk about.

Gardner served as the executive vice president and thought leader for Compuware, a Fortune 1000 Corporation, after it acquired ProviderLink, a healthcare IT exchange he founded.

As a writer, David is author of a popular book on entrepreneurship called The StartUp Hats. He has published many articles and forward-thinking white papers on technical innovation, entrepreneurship and economic development. Among other firsts, Gardner is credited with founding and launching the first software-as-a-service venture in NC (PeopleClick).

Q&A with David Gardner

What was the epiphany for each in your (1) career choice and (2) the decision to build your business?

Gardner: With degrees in philosophy, theology and dead languages, the best thing school did for me is to leave me with no marketable skills. I needed to make money and pay back student debt but no one would hire me. If no one will hire you that’s a great push towards entrepreneurship. That was the epiphany, no one is going to hire me so I have to figure out how to make it on my own. This lead to seven start ups and a two venture funds.

What are lessons from your experiences that others can learn from, especially mistakes to avoid?

Gardner: I think my biggest mistake was in not seeking out more mentors and advisors early in my career. It’s true that there were a lot less efforts and ecosystem to help entrepreneurs back then but still most of the blame is on me for not vigorously seeking out those that could have helped me void many of the expensive lessons I needlessly learned the hard way.

What would be your biggest do-over?

Gardner: One of my seven startups was not successful. I refused to give up and as a result sunk far more time and money into it than I should have. A venture can survive about anything except the lack of a market.

What do you value most (family, faith, friends?) outside of business and why?

Gardner: What motivates me most today is helping first time entrepreneurs.There is nothing on the planet more passionate, tenacious or resourceful as an empowered entrepreneur. I’d like to continue having a front row seat to that for as long as I can do it effectively. I have the most wonderful wife, any man could hope for (Gardner and his wife Cheryl have been married for 27 years). So as long as I can do what I love all day and come home to her each evening, why would I change a thing?

Did those values contribute to your success?

Gardner: Yes. I think genuinely desiring and seeking out win-win engagement is the secret to success with customers, investors, employees and business partners. Make sure everyone has something to gain that is worth their time and proportionate to their investment.

David Gardner, Cofounders Capital founder and partenr speaking at the Cryptotina event. Cofounders Capital photo.

What’s the next chapter in your life and why?

Gardner: I see a fund III in my future and expanding our investments in NC.   I’d also like to write another book based on things I’ve learned as an early stage venture capitalist.

Which of your startups was the hardest?

Gardner: The one that didn’t work

Which was the most fun?

Gardner: What I’m doing now running a venture fund by far.It’s like having dozens of startups at once but you mostly just focus on the really important stuff and are far more appreciated.

Which do you think had/has the most important mission?

Not sure I understand. My personal mission is to always be relevant. Make the world and those around you better. Make sure that everyone that crosses your path is a little better off because they did so.

You’re on a lot of company boards. What sort of contribution do you make?

We do not get compensated for serving on portfolio boards. It is just part of our job as investors. We take our board seats very seriously as guardians of the company and overseers for our fund investors. We are involved in all major company decisions, strategy, key hires, fund raising, equity grants, etc. We are also often listening in on sales calls, potential partnerships and interviewing candidates, reviewing financial statements and forecast, approving budgets, etc.  We are very involved in helping our companies raise the next round of funding, working on their pitch decks, positioning and making introductions. We are advisors to the CEO and often a sounding board.

Did studying music, theology, philosophy and dead languages help you in your career?

Probably. Good communication skills are critical and schooling teaches you to think and write effectively.  But honestly there are few right and wrong answers in business. The correct answer is almost always, “it depends” which is hard to teach in school. Experience is the best teacher…the only problem is that she gives you the test and then the lesson! I also did three years at NCSU studying computer science, but eventually decided I needed to do payroll, not homework.