Confessions of a serial entrepreneur

Like many of you, “I’m not from here.” But I have made a life here and can’t imagine living anywhere else. North Carolina’s combination of land, culture, education, work ethic and just pure livability makes us the envy of the rest of the country.

I say that as someone who has turned down multiple opportunities to leave and as someone who has recruited dozens of people to the area to work for my companies. If you don’t believe me, just read all the articles through the years that have named this area as one of the best places in the country to live and work.

I arrived in the Triangle in 1982 to go to graduate school at N.C. State in Raleigh. A year later, I took a programming job working for one of the early startups in the area that sprung out of layoffs from the local Data General facility – the same facility made famous in Tracy Kidder’s Pulitzer Prize winning book, "The Soul of a New Machine." Three years later I co-founded my first technology company as a bright-eyed, and possibly overconfident, 24-year-old. Since then, I’ve co-founded, built and exited three local technology companies and have been an advisor, investor, board member and unofficial “coffee buddy” sounding board to dozens of others.

Along the way, I’ve made some excellent business decisions, gotten lucky more than once and also made some incredible mistakes. As I look back on these experiences and spend more time with younger, first and second time entrepreneurs in my new role as an early-stage venture fund investor, I’m amazed at how many of the issues, challenges and opportunities are pretty much the same ones I have experienced over the last 35 years.

I find that the “getting lucky” part is hard to replicate. For example, one of my companies signed a $1/copy deal with Microsoft (Nasdaq: MSFT) for every copy of Excel that they shipped for five years. I’ve been asked thousands of times by others how they could do something like that as well but, so far, it hasn’t happened. That was an example of being at the right place at the right time and if I knew how to replicate it, I would have done it with my later companies. And, if I could tell you how to replicate it, I would be the most popular TED Talk speaker ever.

On the other hand, the opportunity for excellent decisions and incredible mistakes has come up again and again through the years and across the dozens of startups I’ve worked with. Part of the process is balancing the good decisions with the mistakes that inevitably come along. By my count, there are five big themes, places to make those good decisions or tragic mistakes, that come up with almost every new up-and-coming technology company. Almost all questions or startup life-or-death decisions are about:

Over the next few months, in this column, we are going to look at each of these areas and delve into some specific examples from my life and business experiences. No problem or opportunity has just one answer and just because something worked at one company doesn’t mean the same will work for another, but I do believe there are methods to approach specific questions that come up again and again that work well for finding the best solution.

Entrepreneur Richard Holcomb is the manager and general partner at North Carolina Venture Capital Fund.