15 Years An Entrepreneur

15 years ago I cofounded my first startup. Now, with seven startups under my belt, some big successes, some small successes, and some, ahem, "less than successes," it's amazing to think about how pivotal that decision to try the entrepreneurial path was.

It was my junior year in college and I had been working part time and summers for UUNET, the world's largest and fastest growing Internet Access Provider, during the peak of the Internet boom. UUNET was amazing when I started there but had grown so bloated and inefficient that I was interested in exploring other options for my last summer before graduation.

Many tech companies - large and small - recruited Rice computer science and electrical engineering majors so I went to career fairs, had interviews, and received several job offers. The best offers came from tech startups. They flew me out to lavish recruiting weekends, paid high salaries, and offered the chance to work on bleeding-edge technologies. Those weren't the aspects that really appealed to me, though; what really interested me was the opportunity to make a meaningful impact on the success or failure of the business.

While I was mulling over the offers, I reconnected with two Rice CS seniors whom I had met during a programming language theory class. They had both accepted job offers from big companies but they wouldn't be starting those jobs until the Fall. They had a [software-based] business idea and intended to spend the entire summer launching a startup around it. If they weren't successful, no worries, they would just start their jobs. If they were successful, though . . .

Long story short: they invited me to join them in starting the venture, something which had never occurred to me before. Now I had a much more complex decision to make: go with one of the "safe bet" options or help start something from scratch.

Of course I decided to cofound the startup. The way I saw it, this was the perfect time in my life to take a big risk; I didn't have kids to feed or a mortgage to pay. Plus I just felt 100x more inspired about the idea of helping to build something from scratch than I did about being a cog in someone else's wheel.

This is, I think, the essence of why I have always (In hindsight, the warning signs have been present since at least elementary school!) been drawn to entrepreneurship: self-efficacy. When the game is on the line, I want the ball - and entrepreneurship is the career equivalent of exactly that. I don't want my destiny anywhere but in my own hands.

The other aspect of entrepreneurship that I really appreciate is its ability to effect great change with no upper limit. Having grown up in the shadow of the space industry, I have always been inspired by the ad astra mentality of solving huge problems. In a capitalist world, entrepreneurship is the most efficient platform for solving such problems today and scaling those solutions up tomorrow.

That first startup was such a bumpy ride. Funded on credit cards . . . Multiple business model changes without a customer in sight . . . and one of our cofounders got scared and dropped out. But it was a grand adventure - and one with a happy ending. Suffice to say, the self-efficacy and scalability were addicting and I've been [ad]venturing ever since!

Entrepreneurial Leadership

Last week I was invited to give a talk on a topic of my choice to the team of a high-growth startup in Durham. Because leadership challenges often cause friction during times of high growth, I chose to address the topic of entrepreneurial leadership. Check out my video below and let me know what you think!

Leadership Journey

12 years ago today - 1/3 of my life ago - I accepted my first chief executive role. While I had been elected to and selected for leadership roles during my scholastic and athletic careers, this was the first time a Board of Directors actually hired me for it.

That first chief exec role was tumultuous, challenging, exciting, and rewarding. During my tenure I developed lifelong friendships and grew substantially as a leader. I made many mistakes - but I learned a great deal as well.

Ultimately I learned that leadership could be a great power for good and I shipped off to IMD to expand my horizons and capabilities. Every day since then has been a deliberate step in an ongoing leadership journey.

The journey continues but today I pause to reflect on the big milestone of 12 years ago and how significantly it has impacted my path.

“It's a dangerous business, Frodo, going out your door. You step onto the road, and if you don't keep your feet, there's no knowing where you might be swept off to.”

― Bilbo Baggins, J.R.R. Tolkien's, The Lord of the Rings