The Power of Second Chances

Finding hope in humanity behind bars

It’s been 48 hours since we collectively elected Donald Trump our 45th President. I’m sitting on a tour bus, before dawn, heading east from Los Angeles. Like my fellow passengers — a decidedly white-collar convoy of creative, VC, and ad tech professionals — I’m silently looking out the window, trying to process the events of the last few days.

As we drive further from the familiarity of the city and the sun crawls higher, manicured lawns give way to desert chaparral. Whole Foods to Safeway to Dollar General. Strip malls to boarded up motels. I’m thinking about divides. Urban and rural. Privilege and poverty. White and other.

We pass Palmdale, Mojave, the highway becomes a single-lane road, the ride gets bumpier. I vacillate between feeling car sick and something more visceral. Like that gut-wrenching sense of grief that engulfs you when the world is pulled out from under your feet, and you didn’t see it coming.

Finally, we arrive at our destination: The California City Correctional Center. An aberration of concrete, industrial steel, and razor wire in this desolate stretch of the Northern Antelope Valley. The only other signs of human development are a handful of RVs dotting the periphery of the parking lot. Probably families visiting loved ones inside, I think to myself.

And that’s what we’re here for today, too. To connect with those inside. In the wake of a bilious and all-consuming election, when the only thing shattered is our confidence in fellow citizens and trust in each other, we’re feeling lost and disillusioned, frightened and resentful. But we’ve been told to pick ourselves up. To keep going. To do something, anything, for someone other than ourselves. So with that in mind, a group of us at enso have enlisted with Defy Ventures to coach inmates on entrepreneurship skills.


Walking down the prison hallway, under fluorescent lights and strict instruction to stay between the yellow lines, we hear the roar of a crowd as guards in full tactical gear lead us to a rec room. “No running in prison!” a well-dressed woman, who turns out to be Catherine Hoke, the founder of Defy, shouts at volunteers as we head through the doors. I’m confused by where we would even be running when it occurs to me that it might be back to the security gates.

But that initial fear evaporates as we run (or rather, speed walk) the gauntlet of a hundred-odd inmates lined up in two rows, high-fiving us as we make our way through the cheering crowd. The most striking thing about the prisoners isn’t their giant, Bluto-like arms, covered in patchwork tattoos. It’s their unwavering commitment to eye contact. And the fact that they’re all yelling my name as I pass them. I forgot I’m wearing a name tag.

From there, our day with the inmates — or Entrepreneurs-In-Training (EITs) in Defy parlance — starts with icebreakers. There’s awkward dancing. Verbal commitments and affirmations. Forced hugs. Like, really long hugs, mandated at six seconds or longer. But only between volunteers, never with EITs. “Do not hug the prisoners!” Catherine warns again, in a tone that lets us know we do not want to find out what happens next if we cross that line.

Now, as someone who struggles with social anxiety, I should be evaluating the drop-down menu of excuses to bail: food poisoning, panic attack, low blood-sugar. But I’m surprised to find my guard down, my heart opening up.

Since Tuesday’s election, I’ve been numb. But suddenly I’m feeling again. Big feelings too: empathy, vulnerability, and profound heartbreak for the circumstances of the EITs, who themselves have no pity for whatever’s in the rearview mirror, only acute focus on what’s ahead in the windshield.

We move onto business coaching. Working in speed-dating format, we meet with dozens of EITs, reviewing their resumes, giving them feedback on interview skills, and evaluating their business plans. There isn’t a single person I meet that I don’t wish I had more time with.

Throughout the day, the EITs continue to give volunteers far more than we can give them; they honestly, selflessly set an example that we humbly follow, tears streaming our faces. What’s truly remarkable is the EITs’ commitment to being present in this experience, given the rollercoaster ride they’ve been on this week.

See, here in California, almost two-thirds of voters have handed Governor Jerry Brown a decisive victory in his efforts to pass Prop 57, a progressive plan to reform our state’s criminal justice system; one that could help thousands of nonviolent offenders see early parole. At the same time, those same parolees would be released with a deck that’s increasingly stacked against them, with stop-and-frisk police tactics, and the threat of mass incarceration of undocumented immigrants. Think about it — what message does it send when the share prices of private prison companies skyrocket the day after Trump gets elected?

Yet the EITs are all-in. They comfort us as we wrestle our own personal demons. They reassure us that the losses and inadequacies we struggle with aren’t inconsequential in comparison with their own. In return, we let them know that we fundamentally believe in them, that we judge ourselves more harshly than we do them.

Towards the end of the day, the EITs and volunteers stand facing each other, on two sides of crooked lines taped on the linoleum floor, completely exposed to one another, as Catherine leads us through the “walk the line” exercise. Now, there other volunteers, like Mark Suster of Upfront Ventures and Brad Feld of Foundry Group, who describe this ritual far better than I could. And I encourage you to read about their experiences to understand how it equalizes the haves and have-nots.

But on this particular day, we witness the CEO of a Fortune 200 company standing across from a man who saw a pregnant woman stabbed in his home when he was just six years-old. Neither is innocent, and neither is posturing. They were both born to teenage mothers, both struggled with poverty. Today, one runs a global software firm with a market value in excess of a hundred billion dollars, and the other is trying to launch his own startup. Both are natural-born hustlers. Both will learn from each other.


B y the time we head back out the gates, we’ve been broken down and built back up with an renewed sense of purpose, to help each of these entrepreneurs defy their odds. Ready to run through walls to do whatever we can, we’ve all signed up for future trips back, and made financial commitments to supporting more of this transformational work.

After all, Defy Ventures has produced more than a thousand incarcerated graduates, more than half of whom have created over a hundred companies that employ hundreds more inmates. Moreover, its graduates have a 3.2 percent recidivism rate within three years, a fraction of California’s overall rate of 54 percent. And that in turn is successfully slowing the cycle of poverty that prison has on low-income families.

On the long ride home to LA, our group is quiet and introspective. Reminds me of the bus trips back from summer camp, a rite of white privilege that seems trivial in the context of what we experienced today. I’m thinking about second chances.

Second chances for careers. Over the course of my stint in advertising, I’ve sold fried chicken to kids with a cartoon colonel, gut-bomb burgers to bros with bikini-clad celebutantes, shoot-em-up video games, and energy drinks, a rap sheet that should disqualify me from working in the social impact space. Yet I’ve found a community of likeminded reformers who’ve welcomed me with open hearts into their shared mission to create impact.

Second chances for companies. I’ve worked with global monoliths — the likes of Walmart, AT&T, Microsoft— that many judge as beyond redemption. Reality is, when you’re that big, you’re going to make mistakes. Lots of them. But in owning these mistakes, and using their size, scale, and success to give back to the communities they serve, these companies can drive positive impact in ways that citizens and civic organizations simply cannot.

Second chances for people. I know that long after I get back to the familiar rhythm of my life in west LA, I won’t look at or think about someone with a criminal past in the same way again. I will consciously remind myself that if we were all judged by the worst thing we’ve ever done, we would lose the capacity to love ourselves, and each other.

So it’s fair to say that I’ve found the hope I was looking for, albeit in an unlikely place. And, like the EITs I’ve met who are transforming their lives through positive actions, that’s enough to keep me moving in the right direction — forward.


Sean is Head of Strategic Growth at mission-driven creative studio enso. Read more at medium.com/enso and find us at enso.co