A few hours after we arrived at the maximum security prison in Lancaster, Cat Hoke, Defy Ventures’ Founder & CEO, asked us to “step to the line”. Volunteers on one side of the line; EITs (participants in Defy’s program are not “prisoners”, they are “entrepreneurs in training”) on the other. Cat read a statement; if it applied to you, you stepped forward.

“If you graduated from high school, step to the line.” Every volunteer stepped forward, less than a third of the EITs did.

“If you have a college degree, step to the line.” A few gasps from the EITs as nearly every volunteer stepped forward, and every EIT stepped back.

“If you had a parent in prison when you were a child, step to the line.” More than half of the EITs stepped forward, and shook hands in solidarity with the handful of volunteers who were also at the line.

“If gunfire was common in your home or neighborhood growing up, step to the line.” More than half of the EITs stepped forward; none of the volunteers did.

“If you’ve been convicted of a felony, step to the line.” All of the EITs stepped forward, joined by two of the volunteers.

“If you’ve committed a crime for which you could have done time, but didn’t get punished, step to the line.” All of the EITs, and roughly half of the volunteers, stepped to the line.

“If you lost your innocence before you were 20 years old, step to the line. … 15 years old… 12 years old… 10 years old… 8 years old… 6 years old…” The last EIT stepped back from the line when Cat said “4 years old”. That EIT later explained to me that he was 4, sitting next to his Uncle when his Uncle was murdered in his living room, by family members.

Over the next 20 minutes, everyone in the room confronted crimes committed, loss, regret, shame, a loss of innocence. The EITs live with the repercussions of the crimes they’d committed each day. As a volunteer it was the most public exhibition of privilege that I’d ever personally witnessed.

The United States has 5% of the world’s population, yet we have nearly 25% of the world’s prison population. Our prison population has grown nearly ten-fold in my lifetime. After my day with Defy, I asked friends who work in the criminal justice system for additional resources about mass incarceration in the United States, and they recommended two books (The New Jim Crow and Just Mercy) and a recent Netflix documentary, 13th:

If you’re curious about the deliberately racial foundation on which mass incarceration is built, you should read The New Jim Crow or watch 13th. We now imprison a larger percentage of our Black population than South Africa did at the height of apartheid. Once incarcerated, individuals often lose access to many of the federal assistance programs designed to help our least fortunate. In most states, they lose the right to vote. Whether they get it back (and when) varies by state. Once released from prison, the lack of assistance makes surviving and thriving exceedingly difficult.

This is borne out by the numbers: the prison recidivism rate in the United States shows that once you’ve been in prison once, you’ll almost certainly go back. Over two thirds of prisoners who are released from prison are back in prison within three years.

Enter Defy. Defy’s mission is simple: “to transform the lives of business leaders and people with criminal histories through their collaboration along the entrepreneurial journey.” I received an invitation from Brad Feld and Mark Suster to join a group they were assembling for Defy; we were part of a group of CEOs, founders, and VCs who traveled to the prison to serve as judges for the pitch competition taking place that day.

(photo credit: Tom Kubik.)

Each EIT spent weeks practicing their pitch for a startup they could start once they were released from prison. Defy requires that each startup have the potential to be cash-flow positive by the third month after they’re released — if they have legit money coming in, they won’t be tempted to return to crime to make ends meet. (Memo to my Silicon Valley friends: this “cash-flow positive” idea sounds intriguing.)

The pitches were simple: in the first round, I heard pitches for a custom jewelry business, a mobile dog grooming business, and a grant-writing business. In the second round, I loved the boat detailing business — Edwin had done his homework, knew how many boats were registered in L.A. County, knew that the current market was under-served, and knew he could turn a profit offering his service at a lower price-point than the competition. It will be a great business.

I’ve written before about what makes a great pitch. Inside prison, the best pitches were no different than the portfolio company pitches I see every day: they defined the problem, quantified the impact, explained the superiority of their offering, and highlighted why they were the right people to build this business. This is the first time I’ve heard anyone speak to their work as a drug dealer — highlighting supply chain management challenges, security, marketing, budgeting, distribution, and customer acquisition innovation — to explain why he’d be the right person to build this business. While you probably shouldn’t highlight your own drug dealing history in a VC pitch, talking about past work experience shipping product is exactly how you convey credibility with your audience. We had no doubt he could execute on the plan he was describing.

(photo credit: Tom Kubik.)

After each pitch, we’d give feedback — on the pitch, on the business itself. After one pitch, I told D. that he had a great idea, that he’d clearly found a great way to solve a real problem. An hour later, D. found me, with tears in his eyes: “I’ve never had anyone tell me I had a good idea before.” I thought about all of the times over the years I’ve told my kids about their good ideas. Hundreds? Thousands? D. had never heard it once.

The pitch competition is the final day of a six month program, and it ends with the men wearing caps and gowns and receiving a certificate from Baylor University. All 45 men passed the final exam; their group had the highest average passing score in Defy’s history. The man who scored highest on the exam — 97% — was sentenced to life in prison as a juvenile; he immigrated to the U.S. at 14 and taught himself English in prison. (By the way: the US is the only country in the world that sentences juveniles to life sentences without the possibility of parole). Fewer than half of the men had ever worn a cap and gown.

Defy is five years old. In those five years, fewer than 3% of their graduates have returned to prison. Of their graduates, 150 have started businesses, and they’ve hired 350 other Defy graduates to work in those businesses. It costs Defy $500 to give these men hope for life after prison; it costs the state of California over $60,000 every year they spend behind bars.

I was transformed by our shared humanity, by the gratitude these men showed us when we spent a day with them, by the obvious impact we had on their confidence in their plans after prison. The ROI for my day in prison is measured in the personal commitment to improving the very real problem of mass incarceration in America. That the financial ROI is so extraordinary is a bonus.

(photo credit: Tom Kubik.)

The prison I visited is part of the California Department of Corrections and Rehabilitation, whose mission statement says: “We enhance public safety through safe and secure incarceration of offenders, effective parole supervision, and rehabilitative strategies to successfully reintegrate offenders into our communities.” (emphasis mine)

To spend a day surrounded by these men is to explore what it means to rehabilitate, and to give them hope at a life outside of prison in the community. It was a profoundly moving day, I’m grateful to Mark Suster and Brad Feld for the invitation, and so thankful to Cat Hoke and the Defy team for making the day possible.

Defy’s goal for EITs is to keep recidivism low. For volunteers, it’s the opposite. I’m scheduled to go to prison again next month. It’s a couple hours outside of San Francisco; if you’re interested in joining, DM me for details. If you’re not in the Bay Area, Defy has programs all over the country. You should go. It will change your life, and it will change the lives of dozens of women and men who are desperate for the opportunity to learn from you.