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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 May, Redlitz and Parenti give a party at the KickLabs building to thank everyone who has helped the Last Mile and to share some exciting developments. “The Last Mile is going crazy, in a good way,” Redlitz says. He announces that a new incubator session is beginning at San Quentin on September 5, but this time he and Parenti will not be running the show. They are handing the baton to two women who work in other San Quentin programs and have assisted regularly with the Last Mile. Instead, he and Parenti will focus on expanding the program into three additional penitentiaries: Folsom State Prison, Calipatria State Prison in Imperial Valley, and Jackson State Prison, 40 miles from Ann Arbor, Michigan. Exciting, yes, but surely also fraught with risk. I ask Redlitz whether a teacher without his gravitas and connections is going to have the same rapport and success with the students, but he has no doubts. “For us, it’s planting the seed for everyone else to start planting the seed. That’s really the nature of Silicon Valley,” he says. “I see this like a franchise. Each program will have its own flavor. And, eventually, its own Chris and Beverly.”

Redlitz’s friends and colleagues are eagerly raising their hands to teach classes and serve as mentors, to attend Demo Days, and even to provide entry-level internships and jobs for future parolees. A Richmond-born VC interested in youth development has volunteered to partner with fellow Richmond-ite James Houston, a Last Miler released in May, on an after-school program called Teen Tech Hub. RocketSpace CEO Duncan Logan extended Kenyatta Leal, a personable three-striker serving 25 years to life for firearm possession, a job offer before he was even released on July 3. “I can’t wait to get my hands on him,” Logan said in May. Leal, the fifth Last Miler to be released, began at RocketSpace on July 18.

Then, in July, Rally’s CEO calls Harts into his office to share two pieces of news. The first is that Harts’s boss, Warshaw, is changing jobs and will no longer be his supervisor. The second is that Harts will have a new boss—if he accepts the company’s offer of a permanent position as business development associate. Harts is over the moon.

Of course, not every Last Miler has such a Cinderella tale. After 18 years of incarceration, Felix Lucero was found suitable for parole during his Last Mile program, so he never completed the course. Redlitz assured him that he could finish outside and get all the benefits, but Lucero hasn’t pursued this. “I’m not sure I want to be an ex-prisoner forever,” he says. “For so long, [being an inmate is] who you are. Then you get out and you’re like, ‘Am I still that guy? Do I have to be?’” The implication is that Last Milers trade on being ex-cons to get jobs and special treatment. But Redlitz hasn’t given up on Lucero: “I ping him regularly,” he says.

Redlitz hasn’t had to face the scenario in which an internship doesn’t end with a real job offer, but he insists that he’s not banking on immediate permanent placements. “Nobody is guaranteeing a job,” he says. “I have to assume that most of the guys are going to have to find employment outside [of their internships]. If we don’t approach it that way, we’re not going to get the commitment from companies.” He believes that starter jobs will produce the momentum necessary for the interns to move forward. “It’s enough time, I think, for them to start to get reacclimated, but it’s less than a $10,000 commitment for the employer.”

Redlitz also hasn’t had to face the challenge of scalability, as critical for a program like the Last Mile as for any startup. The magic of this program is its high touch, lend-a-hand approach—which may prove difficult to provide to a large number of participants at one time. Another uncertainty is what will happen in the long term to Last Milers. Will their lives truly be changed? Will success stories like Hart’s become more than anecdotal oneoffs? Can transformation be maintained for 1, 5, 20 years?

The primary question that Redlitz constantly faces, though, is why criminals deserve a leg up when many other people who have obeyed all the rules never get any support. He has an easy answer: We all benefit from helping prisoners reintegrate into society. “When you realize the kind of money we’re spending to keep them in, that’s taking away from people on the outside,” he says. “Let’s make them successful, and we’ll have more money to serve everybody.”


Originally published in the September 2013 issue of San Francisco

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