Nothing ventured . . . .

This post is derived from an article that I was asked to write for my high school alumni magazine (print, not online). The article discusses part of the founding of True, so we thought it might be of interest more broadly to entrepreneurs.

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The Northern California afternoon was hot and sunny. I walked to the railing and saw Silicon Valley stretched out before me. As I considered the power of entrepreneurship and innovation in the valley below, the weight of my decision hit me. Just a few minutes earlier I notified my employer that I was leaving to start my own firm. There was no turning back. It was June 2005, and one of my career’s most significant transitions had just begun.

Though I envisioned this moment many times, I was shocked by the strength of my conflicting emotions. I was exhilarated, uncertain and yes, afraid. The challenge I was about to undertake would risk my savings, entail a year of non-stop travel and require a rigorous audit on the entirety of my professional life. The odds were against me. Starting a new Venture Capital firm is hard to do, and most new efforts fail. Investors think new firms are at a disadvantage, so they are reluctant to invest in all but the biggest firms. The big get bigger, and the perception is that bigger is better. I believed small firms had many advantages.

My timing from a personal standpoint wasn’t exactly ideal either: I had just welcomed my third son Luke into the world (literally a week before I quit), and I knew that my family would need me a lot over the next year. Was this really a smart move? Was it even possible?

Despite the enormity of the challenge, I knew I could build a great firm. As worried as I was of failure, I was even more terrified of not trying. The clarity of the opportunity was so compelling to me that I literally couldn’t imagine not trying. As soon as I “jumped,” I felt the tremendous personal satisfaction (and freedom) of pursuing my dream.

The past twelve months have proved to be a remarkable experience. The transition from vision to reality was a long road filled with bumps and bruises but ultimately reward and achievement. My team and I are now in business, and we are working on exciting investment opportunities with great people. It feels fantastic.

More remarkable than our specific success is that my story is the same story shared by founders of the largest companies in the world, and also of the smallest. The corner store in your town most likely started because a resourceful entrepreneur envisioned a better tomorrow, risked a lot and worked hard to bring a vision to your neighborhood sooner, better, faster.

To succeed, I relied on lessons learned early and honed throughout my career: experience is important, homework is a must, passion is key and people are everything.

For the better part of the prior fifteen years I was a venture capitalist in larger firms. This experience gave me a good vantage point on the state of the market. Like most financial markets over the past 15 years, the VC market had grown significantly. Bigger investors created bigger funds which chased bigger deals. I witnessed this growth and watched the emergence of a large, unaddressed market for smaller, earlier deals. I envisioned a new firm designed to cater to the needs of younger companies, and I was passionate about working in this early stage of company formation.

But experience, passion and vision weren’t enough. My education and career had taught me the importance of having great people on your team. From my mentors and advisors to coaches and teachers, talented people had a huge impact on my career. One particularly influential mentor once told me to, “choose your friends wisely.” I followed his advice in starting True, and my people choices proved to be the most important decisions I made during this transition. To build my team I emphasized trust and integrity above all other qualities.

Homework was critical, so I reached out to mentors and others in the industry, including competitors. I asked for their advice. Did my idea for a new firm make sense? Was our strategy sound? What was I overlooking? These colleagues provided exceptionally valuable insight and helped me refine my thinking. They vigorously debated my plans. Elements of their experiences would later guide me through many of my specific challenges. These mentors also encouraged me to go for it, and overwhelmingly affirmed my personal belief that the only failure would be a failure to try. Without this feedback and counsel, I could not have succeeded.

Starting your own company is a very trying personal experience. It is also a delicate emotional tight rope. When your vision differs from others, there are many doubters. Other people don’t understand why you are risking so much. You need to be confident in yourself and your vision, but too much confidence will kill the chances for success. In order to keep my wits about me, I reached out to family and friends, in particular my wonderful wife of 8 years and my closest friends.

During one particularly tough period mid-way through this process, I spent a weekend in Duxbury, MA with Rob Fawcett and Todd Needham, two of my best friends from high school. Over the weekend I laid out my situation and my doubts about success. They knew me best. I trusted their opinion. As I loaded up to leave Sunday night, they told me I could do it and gave me confidence that I was on the right track.

One year later our new firm is in business. We are now working hard to build value for early stage entrepreneurs. The past year of transition taught me a lot about myself and reaffirmed my core values. I now place even more emphasis on trust and integrity in my relationships, and I am committed to helping others like so many others helped me. Hopefully fellow entrepreneurs read this and realize that nothing that I did during this transition was particularly remarkable or unusual, and my experience is applicable to all entrepreneurs. The challenge and satisfaction of reaching for a dream kept me going throughout this transition. I had to try for it, there was no other option. In life and in business our time is short; make the most of it.

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