Entrepreneurs and Inmates Are Not So Different — My Day in Prison

I spent last Thursday in prison with inmates convicted of murder, burglary, drug charges, gang activity, and more. Some men had been there for more than 35 years, longer than I have been alive, and…

I can’t wait to go back.

When Defy Ventures invited me to be a judge at their first ever pitch competition inside of prison, I accepted immediately. As one of their first mentors when they launched in the Bay Area a year ago, I was accustomed to working with EITs (entrepreneurs-in-training) who had previously been incarcerated.

Me and my EIT, Jessica Nowlan, who won her first “white belt” business plan competition for her business, CreateShoppe.

However, when Thursday morning came around, I felt a little nervous. Solano State Prison feels like a huge, sad, vacant middle school. Holding my photo ID and car keys, the only items we were allowed, I walked inside a large rec hall with many other volunteers, including directors, VCs, executives, lawyers, and founders from Google.org, Dave’s Killer Bread, PopGourmet Foods, and other local startups and companies. Waiting for us was a sea of men wearing all blue, of all sizes, races, and backgrounds, a memorable few with face tattoos. Some stood on the side nervously, while others tried to engage with as many visitors as possible (just like any networking event or middle school dance.)

We did a series of ice breakers, but the best one was the line activity, a simple game with a line of tape down the center of the room with inmates on one side and volunteers on the other. As statements are read aloud, you take one step forward to the line when the statement is true. You raise your hand if the statement is especially true.

It started light.

I enjoy country music.
I enjoy hip hop.
I consider myself a great businessperson.

Then it got real, fast.

I’m here on a murder charge.

A surprising number of men stepped forward. The volunteers shifted uncomfortably around me.

Growing up, I heard gunshots in my neighborhood.
One of my parents was incarcerated.
One of my parents has a substance addiction.

Many of the inmates’ eyes glossed over as we dug deeper into our pasts. Many of the volunteers were visibly shaken.

At 18, I was just trying to survive each day.
At 18, the only person I could rely on was myself.
In my past, I had to keep my feelings to myself to stay alive.

Hands shot up on the last one.

Both sides had moments of surprise. The inmates were surprised that the executives shared some experiences with them.

I have missed most of my children’s lives.
I want to be a better person for my family.

The sides were almost equal on the line at this one.

The differences between the two sides were clearly not in values, but in social, racial, and economic areas.

My parents both have four year college degrees.
I have a four year college degree.

You can guess which side was on the line.

I was suspended often or kicked out of school.
I have a problem with authority figures.

Both sides were represented pretty equally, again.

Many of the inmates are natural born hustlers with the same talents I have seen in the Silicon Valley and everywhere — skilled presenters and storytellers with charm, authenticity, and genuine passion. A few men served in the armed forces, army, or marine corps. Many have managed “crews”, P&Ls, and understand the fundamentals of business. One question especially sticks out:

I have committed crimes for which I was never caught.

Quite a few white executives and entrepreneurs stepped forward.

There was a clear difference between skin color dividing both sides of the line. After this activity, one of these white executives put it best,

“I feel like I started my life on third base.”

However, both sides share a common DNA — hustle, rejecting “the system”, wanting to create and design new ways of thinking, not wanting to listen to authority.

We had an amazing, but exhausting day. Men pitched their business ideas to panels of volunteers, were given feedback, and five men even won “IOU” $100-$500 business grants to be awarded post-release. Here they are:

The Top 5

The man in the middle, Charles, one of my favorites of the day, pitched a plumbing business, since he used to work with his grandfather on his plumbing business. When asked how he felt about winning, he broke down crying, and managed to get out,

“I used to feel worthless, and… now I don’t feel worthless anymore.”

We all cried with him.

The man who won first place, Dana, a talented artist planning to open a tattoo business after release, said that he initially didn’t have the confidence to join the program or show up to pitch that day, but “was amazed at what could happen when you choose to try.”

When I came home to my apartment in San Francisco, I walked in the door, laid down my keys, and broke down crying thinking about those men.

I was extremely overwhelmed with a feeling of determination and anger that we are failing so many people. We incarcerate more people than any other nation. Most of those people are black, brown, and come from poor families. This is unacceptable. As a country, we are locking up potential and talent — sons, fathers, brothers. Defy Ventures doesn’t just give second chances. For many they help, it’s their first chance.

Catherine Hoke and her team at Defy Ventures are going to change this.

Their mission to transform hustle — from illegal hustle to legal hustle — is one that every entrepreneur should care about, because they are us.

I call myself an empathy warrior, and since meeting Defy’s founder, Catherine Hoke, over a year ago, she has always been an inspiration to me.

She starts each meeting with bear hugs and encourages the men to access their emotions and feelings, showing them that forgiveness, vulnerability, and self work are keys to their transformation (Defy has only a 3% recidivism rate during their program) while working tirelessly to achieve Defy’s mission.

If you are a VC, entrepreneur, lawyer, anyone in business —sign up for one of their one-time business coaching sessions or mentorship programs in SF or NYC or remotely, or email info@defyventures.org.

If you have a company, consider hiring people with criminal histories. Execs from Dave’s Killer Bread reported that their employees with records are more loyal, hardworking, and grab every opportunity to be trained and promoted.

Or, just donate here. They are trying to close a funding gap by the end of the year, and they need our help.

I am urging everyone, especially entrepreneurs and people who support entrepreneurs, to join me and spread the word about Defy Ventures.