Defy Ventures, Second Chances and Why I’m Voting YES on CA Prop 57

Christopher Webb
6 min readOct 17, 2016
Me with a group of Defy Ventures Entrepreneurs in Training

On Friday, October 15, 2016 I was locked in a room at Lancaster Maximum Level 4 Prison for 10 hours with 60 inmates.

Thanks to Mark Suster and Brad Feld (who co-sponsored the event) I was there as a volunteer with Defy Ventures, a non-profit that I knew little about prior to last week. There’s a lot of information about Defy and their incredible founder / CEO Catherine Hoke online, so I encourage you to spend a few minutes Googling them on your own since I want to focus this post on the inmates I met. Or for a faster overview on the program watch this video…

SOMETIME BETWEEN 10AM AND 8PM ON OCTOBER 15, 2016 MY VIEW OF THE WORLD CHANGED

I went into the day slightly nervous. I had heard great things about the program (and watched the video above), but entering a Level 4 maximum security prison is no joke. “Lancaster” looks like every prison you see on TV. There’s absolutely nothing nice about it. Men wearing blue prison garb walking around in dirt and concrete yards. Guards watching from their posts. Layers upon layers of fences. So when I saw this I assumed the prisoners were just like you see on TV — vulgar, rough, dangerous and every other word that comes to mind. I was wrong.

While the surroundings didn’t change over the course of the day, my opinion of the men in blue garb could not have changed more. Let me be clear, all these men did horrible horrible things at some point in their life (most of them in their teens), but on Friday I came to realize the difference between doing a horrible thing and being a horrible person.

Defy Ventures refers to the inmates as Entrepreneurs in Training (EITs), so that’s how I now think of them and will refer to them. The EITs I met had just completed a 6 month course on business. It culminated with graduation, along with a business pitch contest, which is why we were there.

The day was split between the pitch contest (where the volunteers served as judges) and bonding exercises between the EITs and Volunteers.

All EITs participated in the pitch contest. Throughout the day the contest advanced until there were 5 EITs left in The Finals. They then pitched the entire room (roughly 120 people) on their ideas. The winner, whose idea was to create a company to clear brush in order to prevent forest fires (he’s heard about all the recent fires and wants to do something about it), had the most genuine smile when his name was announced. I’ll never forget it. Ear to ear. He was just so happy. I can’t recall seeing so much joy on someone’s face.

While accepting his award he told everyone that this was his first time graduating from anything since elementary school. Yes, elementary school. The guy grew up in a very different world than you and me.

Winner of the Defy Ventures Pitch Contest

Step to the Line is an exercise where everyone stands shoulder to shoulder in a line that runs down the middle of the room. On one side of the line are the EITs, on the other side are the volunteers. The two groups face each other. Questions are asked throughout the exercise by the moderator (Catherine). If your answer to the question is YES, then you stay on the line. If your answer is NO then you step back from the line by 5 or so feet.

The questions are designed to highlight how similar AND different we are.

Question: “Step to the line if you like hip hop.”

Response: almost everyone on both sides step to the line.

Question: “Step to the line if you graduated college.”

Response: 95% of the volunteers step to the line. None of the EITs step to the line.

Question: “Step to the line if you had a parent spend time in prison while you were growing up.”

Response: almost all the EITs are now on the line, all the volunteers are five feet behind the line.

Question: “Step to the line if you spent time in prison as a teenager.”

Response: Once again all the EITs are on the line, the volunteers are five feet back.

Another 25 questions were asked…

This scene I will never forget. Words can’t explain the look on everyone’s face at this point. There was a real sadness in the room. It hit everyone hard. How could we be so similar, yet come from entirely different places. In many cases only miles apart. It’s clear to all of us that the EITs never had a chance. Their lives were determined when they were kids. Many had been in prison since they were teenagers. Their parents were in prison. And if things remain constant their kids will be in prison. It’s a nasty cycle.

I grew up in a middle class family with all the love, support and money needed to get me headed on the right path. I made a number of mistakes as a teenager, including being arrested for stealing car stereos from Best Buy, but because of my foundation I recovered and moved on. Friday taught me how lucky I had it. These EITs were me in many ways, but without the support. They were born into a cycle that set them on a path towards prison. They’re not bad people, just unlucky.

I should reiterate that the vast majority of EITs in the room serving life sentences have been in prison since they were teenagers. Some as young as 14. The United States is the only country in the world that sentences teenagers to life in prison. It’s not right.

Walking into a room full of “life’ers” is a fairly scary thing. But within minutes the fear goes away. It doesn’t take long to see the good in these people. The regret they have and the life they so badly want to live. More than ever I believe in second chances.

A Defy Ventures Graduate with his Baylor University degree

I’M NOT ALONE

Clearly I wasn’t the only one moved in the room last Friday. I promise you every volunteer at Lancaster last Friday has a new perspective on life and our prison system. Here are a few comments I caught on Twitter over the weekend. Keep in mind these tweets are from successful venture capitalists, whose job it is to place bets on people. Collectively they meet and judge thousands of very smart, talented people every year. They’re anything but pushovers and sugar-coaters. They have thick skins and are hard to impress. And yet, this…

I strongly encourage you to do two things:

1/ Vote YES on CA Proposition 57.

2/ Get involved with Defy Ventures.

I keep re-reading what I just typed and realize it doesn’t capture the day. I’d have to be a truly exceptional writer to match the emotions I, and everyone else in that room felt, with words. This post doesn’t do the day justice. Please experience it for yourself. Go to prison.

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