What I learned from my time in prison
Entrepreneurism and pitches in the most unlikely of places
I recently volunteered to mentor entrepreneurs at Wallkill Correctional Facility through Defy Ventures. What follows are some reflections on my visit to prison.
I mentioned in a recent story that I’m interested in getting outside my comfort zone and expanding my networks to find talented entrepreneurs who are underrepresented and overlooked by the larger venture capital world.
Well, I had an opportunity to do just that when a friend and mentor, Martin Babinec, invited me to join a group of business leaders and investors to mentor entrepreneurs who are starting companies from prison.
The trip was organized through Defy Ventures, a non-profit that focuses on programs that give people who committed criminal acts in their past a second chance through entrepreneurship. The organization was founded by Cat Hoke, an inspiring leader with her own compelling story of how she benefited from second chances.
The program I participated in took place at a correctional facility in Wallkill, NY. It was structured in many ways like a typical startup pitch event with some mentorship, feedback and judging. However, the program also included some unique community building exercises that allowed for connections and learning for entrepreneurs in training as well as the mentors. The entrepreneurs also went through a more extensive educational program leading up to the pitch event. Once they are released, graduates of the program can go on to pitch for funding for their businesses and many of them start companies that employ other Defy graduates as well.
Success stories from the Defy program include founders such as Coss Marte from ConBody and Rob Lilly from Powerhouse Events & Catering. Coss Marte was a keynote speaker at this event and his story is truly remarkable. These founders have transformed their hustle — switching from illegal activities into legitimate and successful businesses.
Typically prison recidivism rates can hover around 77%, but graduates of Defy programs have a recidivism rate of only 3%. There are countless ways that entrepreneurship can change lives for the better, but this one is particularly meaningful for these founders, their teams, and those they serve.
What struck me most about the experience was how much the Defy entrepreneurs have in common with other entrepreneurs I’ve worked with and how, despite the venue, the program was very similar to other pitch events that I’ve attended. Sure, there were some slightly different approaches in terms of the types of businesses, but overall the experience was more familiar than I anticipated. This was partly due to the great effort on the part of the Defy team to create a humanizing and respectful experience that breaks down the boundaries between the entrepreneurs in training and their mentors.
It was also quite apparent from the demographics of the group that there was a disproportionate number of people of color in the entrepreneur in training group. We all know the statistics around race and our justice system, but it was a startling reminder to experience it first hand.
Furthermore, many of the folks in the mentor group had also made mistakes in their life or even committed acts that could be considered illegal, and the only difference between them and the Defy entrepreneurs was that the mentors hadn’t been targeted, caught or convicted. I entered the program thinking of myself as very different from the entrepreneurs in training, but left feeling that we all had more in common than I ever could have imagined.
After participating in Defy’s program, I am more committed than ever to our mission at Chloe Capital of advancing solutions to the gender and diversity gap in entrepreneurship and investing. The power of entrepreneurship to transform individuals, communities and the world has never been so apparent. It’s clear that the opportunity to pursue entrepreneurial dreams should be available to everyone, regardless of gender, race, disabilities or past mistakes.
