I'm a venture capitalist at Transmedia Capital living in Silicon Valley, the heart of the world's technology innovation and investment community. I've been here for 20 years. I never thought deeply about pursuing a social cause or dedicating myself to anything beyond my career and my family. That mindset changed on the evening of October 10, 2010.

It was the first day I walked into prison. I had never been in prison before, nor did I know anyone behind bars. I was not serving time. I was asked to speak to a group of men about business and entrepreneurship. I agreed to speak for 30 minutes.

I didn't think the men inside would understand anything about the basic concepts of business or venture capital. I thought most inmates were uneducated and beyond the point of redemption.

What I discovered that evening changed my perspective of the US prison population and ignited my sense responsibility to help change a broken system and rewrite the narrative.

I was escorted into San Quentin State Prison, one of the most infamous prisons, sitting on the edge of the San Francisco Bay. I was led through a series of gates, down a windy path, through the prison yard, into a small classroom where about 50 men were awaiting my arrival.

After I began speaking, I noticed that many of the men had "the look" that I see in the eyes of founders and entrepreneurs in which we invest, but it was at a deeper level. These men had a look that reflected their primal hunger to learn, and deep desire to build a better life after they served their time. My 30-minute talk turned into a three-hour discussion.

I left prison that evening, thinking about how could I evolve "that look" into something actionable that would help transform these men into successful contributors to our business community when they were released from prison.

I did not realize how much this journey would change my life, make me a better investor, and ultimately a better person.

Since that night, I've spent over 500 days in prison.

As a point of reference, the economics of the issue are dire:

  1. Recidivism rates are over 60 percent in the U.S.
  2. The annual cost of incarceration is $70,000 per inmate.
  3. There's a critical lack of educational resources in our country's prisons.
  4. 95 percent of our incarcerated population will eventually be free.

So the question is: Who do you want them to be?

After digging into the issues, my wife Beverly Parenti and I developed a program called The Last Mile, teaching entrepreneurship and computer programming in prison. This is our "big bet" to change the face of incarceration-based education in America.

The Last Mile is currently in five California prisons (including two women's prisons). Our goal is to become a national program within the next five years. Since we began in 2010, we've had zero percent recidivism from our "returned citizen" graduates.

We're not only preparing men and women in prison for future employment, but we're also breaking the cultural and ethnic divide within the prison culture. When TLM participants walk through the huge steel door to our classrooms, they leave all prejudices aside.

Prisons are very segregated by nature, but not in The Last Mile. Every ethnicity is represented in our classroom, even former Crips and Skinheads are collaborating on projects together.

The men and women in The Last Mile have become in inspiration to me, the Silicon Valley business community, and many of the Transmedia Capital portfolio founders who have visited San Quentin. Employees from Silicon Valley companies volunteer inside and serve as mentors for our graduates. They too, have been inspired.

This inspiration, emanating from one of the most unlikely places on earth, provides hope to incarcerated men and women across the country, and proves that anything is possible.

Hopefully you'll be as lucky as I have been, to find inspiration and a mission that will impact your life and the lives of many others. As we say in The Last Mile, we are all on a journey, "Paving the Road to Success" if we all "Believe in the Process."

Published on: Jul 25, 2017