On the outside, I am an extroverted, sometimes over-the-top cheerleader for my portfolio companies. The Startup Factory (TSF), the accelerator I run, has 31 investments. But I have a secret. I worry. I worry a lot.

At its core, my worry is all about fear. What do I fear?

I am afraid that my investments are bad and I won't return capital back to my investors. I am afraid that my reputation (whatever that is) will be crap and I won't be taken seriously. I am afraid that I will have wasted three, four, five years for no gain. Ultimately, I am afraid that I will be a failure. Again.

Why me, you might ask? I have had success. I co-founded MapQuest, served as the president of Rand McNally, and worked as a corporate venture capitalist. Now I operate one of the best seed investment funds in the Southeast.

But I have had real failures as well. In the late 1990s, I spent a year raising investment capital to roll up and combine a handful of map publishing companies that never materialized. I was brought in as an executive (along with a CEO I had worked with before) of a multimillion-dollar software company that was losing millions a year. We got close to rescuing the company before the recession hit us hard. It is a shell of its former self today.

The Startup Factory is on its third iteration.

You want full transparency? I feel like the successes were lucky and that the failures were entirely my fault. I think about it every day. And I worry.

I'm not the only one, of course. Everyone worries. The difference is I now know how to cope with my own insecurities.

Take credit for the good, along with bad. Ultimately, with age, I have come to realize that I had something to do with both the successes and the failures. There it is. I said it out loud. I am responsible for the successes. I earned that. My brain, my experiences, my personality, and my drive can make positive things happen. This is a positive building block for my own daily psychology.

Develop a support system. A few years ago, a very close friend and I were talking about this issue and how our brains naturally took us to the dark place (we have a code for it--ask me sometime). We were lamenting how peers we knew had seemed to naturally transcend our demons, and we committed to helping each other. We developed a trick for me. I was raising capital for the first iteration of TSF and I would call him before each meeting. He would ask me one question: "Who's the king?" My answer: "I am the king!" Corny, but I like to think it helped put me in a different frame of mind.

Let it go. When I look back on what factors are integral to my successes, I can clearly see a distinct pattern emerge. When I had no fear or worry, I was free to be in the business-moment. I operate best when I have released the baggage of fear. I love this quote from Jack Canfield, "Everything you want is on the other side of fear."

My goal, every day, is to find my way to the other side.

Published on: Sep 25, 2014