The Day I spent in Prison
No, I didn’t get in trouble with the law. I was lucky enough to spend the day yesterday in California State Prison, Los Angeles County, a level 4 maximum security prison, with Defy Ventures. As I sit here writing, I still have tears streaming down my face. Yesterday was the most inspiring and humbling day I’ve had in my 31 years on this planet. We all entered the prison not knowing exactly what to expect. The staff at Defy had us all prepared on what we could and couldn’t wear (extensive list!), what to bring, etc, but no one could have prepared me emotionally for the impact I experienced on October 14th, 2016. I met Cat and Charles through my work with the Techstars Foundation. The day I met Cat, I told her I wanted to go to prison. That desire never changed, instead it came true.
Brad Feld and Mark Suster led the charge to bring a group to this prison. This is a level four maximum security prison. I’m so honored to be part of a group, of 75 Venture Capitalist, Entrepreneurs, CEOs, Harvard MBAs, and the list goes on. It is the first time Defy had more volunteers than the 60 Entrepreneurs in Training (EITs) at this prison.
The day started with things I would imagine. Security, rules, shuffle from one building to another. I’d never been inside a prison. The majority of our group had never been inside a prison. After about an hour, it was finally time to meet the EITs. We were welcomed into the room as if we they were announcing the starting lineup at a basketball game. Two rows of EITs on either side with their hands up. We were welcomed with smiles and high fives. For the next hour or so we had the chance to chat and mingle. We had stickers to exchange. We learned about their businesses. The time they’ve spent behind bars, their hopes and dreams post-release. We were witnessing the value of Defy. It was so human. Just two or three people talking. It didn’t matter what color you had on. All that mattered was that we are all people.
We were then welcomed by Cat, the Founder of Defy. Woah, that woman. She has the most INCREDIBLE presence and can command a room but at the same time break down a room. She taught us how to clap. Golf claps were not acceptable yesterday. We learned the prison rules. One of the rules was no hugging. I had no idea how much that would impact me by the end of the day. We told each other affirmations and committed to leave it all out there and try and keep all our commitments.
We got into groups and heard pitches from three EITs. We asked questions and gave feedback. We ranked them. 45 pitches, 15 tables. These businesses all have the potential to be cash flow positive in 3 months. Then we did an exercise called walk the line. Cat told us there would highs and lows but this was more than I ever could have imagined. We had two lines. One for the EITs and one for volunteers. If each side put our arms out we could touch. She asked us a series of statements. We all started 5 steps behind the line and if the statement was true, you walked to the line
They started simple. Step to the line if you like hip hop, things of this nature… I can’t remember the rest of the easy ones but then it got real. I have been to jail. Most people on our side (besides a lucky few of us!) stayed back. All the EITs are on the line. I have done something I could have gone to jail for Everyone steps forward. Statements like I am ashamed of something I did, I have murdered someone, I have lost a child, At what age did you lose your innocence? Cat counted down. 18, 16, 14, and so on. One guy stayed at the line until she counted down to birth. He says he was born to be a gang member. I experienced abuse as a child. I grew up with one or more parents using drugs or alcohol. My mother or father has been to jail. And the statements went on and got more intense. And the EITs stayed at the line: The longest someone had been incarcerated was 28 years. I broke down. My heart hurt. I had just spent the past many hours chatting and bantering with these guys. But their reality is so starkly different. Most will get out. Some will not. How can we expect recidivism to go down if we spend no time / money / resources on rehabilitation and teaching skills?
The statements continued. I have not forgiven myself. I have not forgiven someone else who has hurt me. Not forgiving myself or others is still hurting me to this day. This was raw. Almost everyone, both volunteers and EITs stayed at the line.
My heart continued to expand and break at the same time. I felt selfish for being given such an amazing life and not being to change how these guys feel or help. But I felt their pain, and they felt mine and that is what was so beautiful and humbling. We have help them understand WHY they want to change.
This whole time you during walk the line you are staring mostly into the EITs eyes across from you (unless you’re balling like a baby…). I got so lucky. Across from me was Eddie. If I remember correctly, he’s a lifer. As of right now, he’s never getting out of prison. Ever. But he had a kindness to him that I didn’t know you could feel without speaking or touching. Empathy. I’ve never experienced anything like it. Eddie changed my life forever, just through our eyes. He never let go of my eyes. When I started to cry, he would smile slightly. Empathy. I’m not sure I’ve ever experienced true empathy from another person. Maybe I have. But not in this way. We transcended our race, the clothes we were wearing, our pasts. Our rights and wrongs. We were at that line to feel for each other, and it changed my life.
The day continued. We saw final pitches and watched a moving graduation ceremony. These EITs received MBA certificates from Baylor University. Most had never never been in a cap and gown or walked across the stage. The smiles were contagious. The pride, the hope. They told us what they love about Defy. How no one has ever believed in them or given them skills or tools to succeed.
We all spent 12 hours away from our phones. Away from our jobs, away from our families and responsibilities. But I never wanted my phone back at the end. Nothing seemed to matter. I walked out wanted to quit my job (don’t worry, I won’t) and change the world. End mass incarceration. Anyone who has known me for long enough won’t find this surprising. I want to help Defy get these programs in every prison in our country.
At the very end of the day before they walked across the stage, Cat talked about forgiveness. What is holding you back from forgiving someone or yourself? Is it because you don’t know how? Defy has powerful courses on forgiveness, and teaches these EITs that even though they might be physically incarcerated, they can grow to better themselves emotionally.
We had sheets of paper where the EITs wrote us notes and we wrote them notes on theirs, think yearbook style. This one stuck out on mine. “The emotions you showed opened me and allowed me to ease some of that pain in which I’m holding. Thank you. — Lucky Leo” No, Thank you, Leo. Thank you for the humility, breaking down stereotypes, opening our eyes, inspiring us, and most of us, helping us to have hope. Hope for you and hope for the world.
At the end of the day, I went to say goodbye to Eddie and thanked him for what he had done today. He said “I wish I could hug you”. We stood as close as we could without getting in trouble and gave ourselves hugs. It was the best hug I’ve ever gotten.
I only hope that I can have one fraction of the impact on someone’s life as they had on mine. I will NEVER forget those faces, those smiles.
Let’s give more people a second chance, let’s equip them with tools to succeed, not to fail again. Prison isn’t cheap (I believe Cat mentioned it costs over $47,000/year for those EITs to be incarcerated). I know it will take a few days to figure out what really matters and re-prioritize my life. But If these EITs can commit to doing something when they might never be free again, nothing should stand in our way. Dream big. Give back. Go to prison. I highly recommend it.
Also, if I had a dollar for every time I heard the EITs encouraging us to vote YES on prop57, I probably COULD quit my day job and save the world. So if you live in California, from the heart of Defy’s California Prison EITs… please vote YES on Prop57 on November 8th.
