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The Inmates and the Entrepreneur

Behind the walls of San Quentin, one Silicon Valley innovator is preparing convicted felons for a new kind of future—in tech.

Former San Quentin inmate and Last Mile graduate Heracio "Ray" Harts.
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Last Mile founder Chris Redlitz.
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The Last Milers
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Last Miler James Cavitt
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Last Miler Larry Histon
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Last Miler Jorge G. Heredia
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Last Miler Thomas Winfrey
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Last Miler Eric "Phil" Phillips
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Last Miler Darnell Hill
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Harts (center) on his first day of work at with CEO Tom Serres (left) and former communications director Nick Warshaw.
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In the classroom, Redlitz treats the men like he does all the entrepreneurs he advises: directly, respectfully, demandingly. It isn’t enough just to outline their business concepts without major fumbles, he tells them. “We need to move to polished five-minute presentations.” The men look more anxious than ever: The realization that a month from now they will be standing before dozens of VIPs selling their ideas—and themselves—is sinking in. Redlitz tries to defuse the tension by sharing his experience at a December TEDx talk he gave about the Last Mile. “Let me tell you,” he says, “I don’t get nervous talking anymore, but I was so stressed I sweated through my shirt. You know what Beverly said?” He glances over at a smiling Parenti. “She said, ‘Just don’t lift up your arms!’”

Next, Redlitz rolls video of the previous week’s pitch sessions for the Last Milers to critique. The men’s presentations are packed with the latest tech jargon: “live-streaming,” “QR codes,” “second-screen trend,” “mobile apps.” It’s hard to tell whether they are just playing back terms they’ve heard from their various guest speakers or have genuinely internalized the concepts, but given that they had never heard of any of this when they started the class, even light understanding is impressive. When the critiques are finished, the men have another go at honing their presentations. Chris Schuhmacher, a lanky guy serving 16 to life for second- degree murder, leads off with an idea he calls Fitness Monkey, an online training concept to help drug abusers create “a healthy addiction” to exercise (Schuhmacher competed in this year’s San Quentin marathon—105 laps around the prison yard). Other startup ideas follow, including a food-waste recycling program and an Etsy-like site for inmate-artists who want to sell their work. Prisoner after prisoner, they outline weighty business propositions to address some of society’s gravest ills: obesity, lack of job training, poorly funded schools.

Harts—weeks away from parole—steps up to explain his idea: a one stop health-and-wellness center for impoverished communities. He talks about a childhood spent on streets littered with drug needles, where the only grocery store was a liquor shop. “My vision for Healthy Hearts Institute is to turn neighborhood food deserts into usable oases,” he says with the polish of a veteran pitchman. “Abandoned buildings will become a LEED-certified fitness facility. Abandoned lots will be gardens.”

Redlitz responds with a satisfied nod, and a fellow Last Miler praises Harts’s use of his personal story to make the pitch compelling (the inmates are learning to support each other so they have a network when they leave prison). Silicon Valley’s young guns, hawking their microvideo exchanges and web-based sandwich delivery services, could learn something from these guys.

Redlitz wasn’t searching for a calling. Despite looking and sounding like a Marin cliché—he and Parenti raise small-flock hens, tend organic peppers and squash, and balance their pH with a cider vinegar elixir—he’s a high-octane profiteer with the millions to prove it. (How many millions, he won’t say.) “We’re not activists at the core,” he says. Parenti goes further: “We’re about the last people on earth you can imagine working in a prison.”

That all changed in 2010, when a friend invited Redlitz to San Quentin to chat with inmates about entrepreneurship. The brief talk became an intense two-hour session with prisoners asking intelligent, probing questions, and Redlitz couldn’t pull himself away. On the drive home, he imagined creating a KickLabs-like program inside San Quentin—a Delancey Street of tech. He would fund the initiative himself. “I could see in his eyes that this was big,” Parenti says. “I knew right then—this is going to be a journey.”

First, though, they had to sell the San Quentin administration on the initiative. Two cultures more opposite than Silicon Valley and San Quentin you could not find. “Remember, prisons are graded on whether anybody escapes, not on how many they teach to code,” says Redlitz. Just getting permission for prisoners to tweet—even with trusted volunteers as monitors and intermediaries—was a yearlong effort. “You can see why no innovation ever happens here,” Redlitz says. “The idea of letting these guys publish to the world was unnerving. It’s like when I used the word ‘disruption’ in Sacramento. They’re like, ‘Disrupt? That’s not a great term around prison.’” 

“Rehabilitation” isn’t a beloved term, either. “The purpose of prison continues to be punishment,” says Jeanne Woodford, who spent 30-plus years in corrections (including five as San Quentin’s warden) and then headed the anti–capital punishment organization Death Penalty Focus. “Rehabilitation is kind of an afterthought. It’s always that money that gets cut first, and it’s so slow in being put back.” Retribution over rehabilitation has roots in the ’70s and ’80s “tough on crime” era. High crime rates and the drug culture drove law-and-order politics, producing mandatory minimum sentencing and three-strikes laws that require life sentences for repeat offenders. An academic view (later discredited) prevailed that prisoners could not be redeemed. “We’re coming out of a 25-year period when rehabilitation was very much out of fashion,” says UC Berkeley law professor Jonathan Simon, director of the law school’s Center for the Study of Law & Society. “The public and even criminologists didn’t have any confidence that we knew what to do. It’s very difficult to change that culture. They retreat to the fear picture.” Prison overcrowding is also to blame, straining resources and shoving rehabilitation off the priority list. “All the space you would have used for rehab programs, you needed for inmates to sleep,” says Bill Sessa, a spokesman for the California Department of Corrections and Rehabilitation.

Redlitz eventually found the right words to convince CDCR and San Quentin administrators to take the leap. “I had to step back and try to get inside their head,” he says. He shared his own experience nurturing entrepreneurs. “I told them, ‘We’re doing things that can translate here. Teaching skills to start businesses. Most of these guys aren’t going to be able to get jobs, so we need to figure out how to get them to be self-supporting.’”

California’s prisons operate on an $8.9 billion budget, more than the state spends on higher education. For every $1 invested in rehabilitation, $2.50 is saved in corrections costs. “There are inefficiencies everywhere,” Redlitz says. “If you could really have an impact on something like this, that’s more than money can buy.” San Quentin officials finally came around, and this spring Redlitz succeeded in getting a new, much larger classroom at the prison to accommodate 27 coding students per term. He’s also jumped into reforming policy that impacts his guys: He and Parenti ran social media for last November’s successful Proposition 36 campaign, which made nonviolent three-strikers eligible for shorter sentences. More than providing job training, Redlitz says, “We’re trying to build a culture of education [in prison]. If you want to get to the Last Mile as the pinnacle, then you have to succeed at all these first steps. There has to be something to aspire to.”

With his big reform vision at stake, Redlitz is extremely selective in picking his Last Milers. The process requires essays, interviews, and staff and peer recommendations. Until the latest session, starting this month, participants were required to be graduates of Patten University, an Oakland institution with a San Quentin satellite campus and the only degree-granting college in the California prison system. This has been easily the most stringent filter: Just 130 inmates have earned a Patten associate of arts degree since 2000. To date, the Last Mile has accepted just 10 percent of its applicants. In prison terms, Redlitz’s guys are the best and the brightest.

Page four: Adjusting to life outside prison