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Some Fundamental Truths This Entrepreneur Learned Mentoring …

As we drove through the first gate and saw the inmates walking the yard, it hit me: I’m heading into a prison. Another gate and several checkpoints later we arrived at the parking lot. All this and we hadn’t even made it to the front door yet. Just one important note: instead of riding on a bus filled with inmates, I was traveling with entrepreneurs, CEOs and investors.

We were at Richard J. Donovan Correctional Facility in San Diego, Calif., for a one-day Shark Tank-like pitching session, the culmination of a year of learning and preparation by a motivated group of inmates. My journey was set into motion a few months earlier when I agreed to participate in Defy Ventures, a program which teaches business skills to incarcerated men, women and youth to prepare them for life outside of prison. Only 40 percent of incarcerated people attain employment in their first year after release. The Defy program is trying to improve that statistic.

Entrepreneur and investor Neil Senturia brought the program to San Diego and spearheaded the one-year training. Inmates had become Entrepreneurs-in-Training (EITs) for an intensive series of courses, online and in-person, on leadership development, executive mentoring, financial investment and startup incubation.

Inmates enrolled in the program are approaching the backend of their sentences, typically after about 10 years in jail. They suffer the stigma of their past indiscretions and struggle to be recognized for who they have grown to become and truly are. What attracted me to volunteer is the Defy program’s success reversing their self defeating way of thinking.

More than 10,000 prisoners are released from jails every week in the U.S. but two-thirds are rearrested within three years. In contrast, fewer than five percent of EITs who complete the Defy program return to prison. To date, the Defy program has helped more than 550 incarcerated individuals across 24 states prepare for life after prison. Defy has financed and incubated 165 startups founded by EITs who have created more than 350 jobs in their communities.

Those results motivated me to become part of something greater that is making a measurable difference. If sharing my experiences with these inmates improved their chances of getting a job or starting a business that improved life for their family and community, I’m all in.

We entered the facility slowly, similar to how we entered the parking lot. Inside, the correction officers stood holding rifles close to their chests. We were given strict instructions such as “don’t attempt to hug an inmate.” Surprisingly, I was more excited than nervous. The prison staff and program leaders were incredibly calming. They assured us the inmates were more nervous than we were. I could relate. I remember my first pitch to an audience of investors.

The EITs told the backstories that lead them down the road they traveled. The deeper we dove in, the more humbled and impressed I was. It was sobering to learn that the children of inmates are five times more likely to be arrested for a crime than average. Seventy percent of children with an  incarcerated parent are themselves incarcerated at some point in their lives.

I reflected on the drastic differences between us growing up. My dad and grandfathers graduated from college and earned advanced degrees in medicine, law and architecture with barely a speeding ticket between the three of them. Each contributed to his community and society in some fashion. One of my grandfathers was a leader the global effort to cure polio in his roles as chief of surgery at a prominent hospital in Ohio and vice president of International Rotary. I am very grateful for my upbringing

The pitch setup at the prison was a cross between musical chairs and speed dating. The EITs rotated in a circle to spend time with each entrepreneur. The catch was they didn’t know if they would be asked to give an elevator pitch, business idea or resume review. The Defy program had prepared them to think on their feet and comfortably interact with multiple parties at a fast pace. Learning those skills is a challenge after years of following prison procedures. Their confidence grew after a few iterations with strategic feedback from us mentors. Their pitches got better and better.

One particular inmate’s pitch struck a personal chord for me. His goal was to start his own food truck business. He was excited to get to work and had everything mapped out — his grandmother’s famous recipe, his projected overhead and startup costs, his clientele and marketing strategy. My brother years prior had started his own food truck business and, after a few successful years, grew it into a popular restaurant in Boulder, Colo. I enjoyed a rapport with the EIT, offering my advice from watching my brother go through the same process.

Sharing personal stories one-on-one with EITs was inspiring, to say the least. I hadn’t expected so much openness or that they would trust me enough to share their worries and stresses.

Sitting there, I reflected how lucky and thankful I am to have been born into a loving, giving family. We’re all dealt a particular hand at birth. What we get is out of our control, but I believe that every individual, with a pure intention, can achieve incredible things beyond what they imagine. Defy Ventures is opening a door for many who never got an opportunity. That’s the type of stuff we should all strive to be a part of.


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