Visiting Prison Again — With Defy Ventures

A few weeks ago, I continued my education on an issue I’m passionate about — criminal justice reform and the prison system — when I participated in a Defy Ventures event at a California maximum security prison. It was an incredibly powerful day.

About 50 VCs and entrepreneurs, mostly from LA, trekked to the prison north of Los Angeles, under the organizing leadership of Mark Suster and Brad Feld and the non-profit Defy Ventures. Defy Ventures, in their own words, “transforms the lives of business leaders and people with criminal histories through their collaboration along the entrepreneurial journey.” Catherine Hoke, founder/CEO of Defy, is one of the most passionate entrepreneurs I’ve ever encountered — and I’ve encountered many passionate entrepreneurs.

From 9:15am-8pm we gathered with the inmates in an indoor gymnasium. The gym looked and felt like any other — except for the multiple signs on the wall that said “No Warning Shots Will Be Fired in the Gym” and for the gunner who paced back and forth from a ledge near the roof of the building, holding an automatic rifle.

The schedule was non-stop. Shaking hands, talking 1:1, listening to their business pitches. Many of the inmates were nervous: some told us that the opportunity to meet us was the biggest opportunity they ever had in their life. We were also nervous: we were in a max security prison. A day full of personal interactions with “criminals” forces you to abandon stereotypes and understand these men for who they are: human beings, flawed like all of us, but human.

The most powerful hour of the day occurred just after lunch. Inmates and volunteers lined up in two lines facing each other. There was about 7-8 yards separating the two lines, and a line of tape on the floor in the middle. We stared at each other across the line. Catherine posed a series of questions and asked us to step to the middle line if the statement was true for us. Example: “If you grew up in poverty, step to the line.” Almost every inmate stepped to the line; almost no volunteers did. “If your parents have been incarcerated, step to the line.” Almost every inmate stepped to the line; almost no volunteers did. And so on. It became abundantly clear very early on — and clear in the most visible way, as people physically stepped forward and back during the questions — that most of the inmates were dealt a set of cards in life that made “failure” a likelihood.

We were asked to maintain eye contact with the inmate standing directly across from us in the lineup. I didn’t know the backstory of the person I happened to line up across from. Then the question: “If you were arrested under the age of 17, step to the line.” He did. Then: “If you have been incarcerated for more than 20 years, step to the line.” He did. Those two questions stopped me cold. He made a mistake as a teenager, and has spent 20 years in the slammer. Are you kidding me? I choked up. Meanwhile, he maintained a steady, compassionate gaze, reaching out to shake volunteers’ hands whenever they stepped to the line.

Afterwards, I went up to him and learned his story. He was in for attempted murder — he had been out with a group of guys one night and one person had a gun and the prosecution proved there was intent to kill. I asked about his time behind bars. He said he spent several years at Pelican Bay, the notorious supermax prison in California, where the entire prison was on complete lock down for three straight years — meaning everyone was confined to their cell 23-24 hours a day. I can’t imagine the effect such isolation has on the human mind. By the end of our conversation, I couldn’t shake the feeling that this guy had been completely screwed by “the system” — the length and conditions of incarceration seemed utterly unjust.

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A year ago, I visited San Quentin State Prison and spoke to a group of 20 inmates about The Startup of You. They had all read the book and our 90 minute discussion was a mind blow — it opened my eyes to a population of people and a political issue to which I was totally blind. I wrote about my experience in this blog post.

I’ve been thinking about the criminal justice system ever since: how unjust the system is to so many, how prisons mete out punishment and yet often fail to cultivate rehabilitation, the philosophical basis for believing in redemption and second chances, among other topics.

My interest has led to me on several paths:

• A friend and I spent a bunch of time brainstorming business ideas that would serve prisoners and their families. There are more than two million Americans locked up and many of them are gouged by predatory companies that supposedly “serve” their families. Specifically, a small number of telecom companies monopolize the phone systems inside prisons and charge ridiculous fees for inmates to call their families. Is there a way to disrupt them
• I watched the Netflix documentary 13th, which is about the mass incarceration problem in America and how it’s connected to race. The film’s title is a reference to the 13th amendment which banned slavery. The film argues that mass incarceration is a modern version of racially-charged enslavement. I highly recommend the documentary.
• I’ve been reading Shaka Senghor’s moving memoir Writing My Wrongs, about his 19 year incarceration for murder and ultimate redemption. Shaka did a tour of duty as an MIT Media Lab Fellow and delivered a popular TED talk. I’ve gotten to know Shaka a little bit and find him inspiring.
• I donated money to The Last Mile and am headed back to San Quentin in a few weeks to speak to another group of men who are reading The Startup of You.

Speaking of The Last Mile, they have pivoted to a model that may, from my perspective, make it one of the most interesting programs in the prison reform marketplace of ideas: they’re teaching inmates how to code! They have set up computers in prison that let inmates code despite the computers not being connected to the internet. Coding instructors on the outside pipe in via live video chat to teach the inmates. Imagine if inmates could get paid for coding while on the inside (prisons as the new low-cost outsourcing option for companies!). And when they get out, the men possess one of the highest paid skills in the modern economy. Coding skills may be the most reliable path to economic self-sufficiency today.

Anyway, thank you to Defy Ventures for all the work you are doing to tackle one of America’s most morally pressing issues. And thank you to Brad and Mark for inviting me on the unforgettable trip.