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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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Amid the dysfunction, the goings-on in the Last Mile’s cramped classroom feel like an act of rebellion—or, maybe, naïve optimism, which amounts to the same thing. It’s a Tuesday night in January, and 13 men in blue and gray scrubs and beanies are sitting in a tight circle. Just outside the room is the prison yard, where convicted robbers, gang leaders, and killers shoot baskets and chat at picnic tables during their free hours. A hundred yards away is East Block, home to all of California’s 733 male death row inmates.

Redlitz, 57, in a burgundy collared shirt, black slacks, and loafers, his face tanned, his body toned by three hour bike rides in the Marin hills, shuts the door, and the room falls silent. “Thirty days from today is Demo Day, so we’re gonna have to start rapidly revising slides,” he announces. The roomful of anxious faces stares back.

The inmates—eight are participants in the current Last Mile class; five others are grads of the program’s first class in 2012 and are here tonight as mentors—are clearly in awe of Redlitz, whose path to tech titanhood has been unlikely in its own way. A onetime marathoner and ultra-runner (injuries eventually forced him to switch to distance biking), he began his entrepreneurial career in 1980 by opening one of Southern California’s first running stores. This led to a 10-year marketing and sales career at Reebok International during the era when the company overtook Nike, hitting $2.5 billion in sales. Redlitz once drove a VW van filled with sneakers around South Central Los Angeles, taking style tips from gang leaders—he says it’s how he learned to talk to tough guys.

In 1994, Redlitz moved into tech, where he was behind a slew of digital media firsts—the first online ad auction marketplace, the first independent online yellow pages, the first RSS ad campaign. The money and industry cred he earned from those scores led, in 2003, to the founding of his San Francisco–based VC firm, Transmedia Capital. In 2011, Redlitz and his wife, a dancer turned entrepreneur named Beverly Parenti, along with his Transmedia partner, Peter Boboff, established KickLabs, an early stage accelerator that nurtures digital media startups. Current companies in Redlitz’s portfolio include Scan, Domo, Kiip, Scvngr, and the breakout hip-hop lyrics website Rap Genius. But the Last Mile is looking like the edgiest, most farsighted thing that he’s done yet. 

The Last Mile is based on the KickLabs concept, with a twist. The program takes inmates through a six-month boot camp in business and marketing, with a heavy focus on the newest tech trends. At nearly every class, a different contingent of Redlitz’s high-profile friends and colleagues offer geeky tutorials, real-life startup wisdom, and pep talks: people like early Apple evangelist Guy Kawasaki, whose book, Enchantment, is required reading; Foursquare engineer Rafi Syed; Josh Kopelman, the founder of and now a partner with First Round Capital; Zappos backer Erik Moore; and Andy Smith, coauthor of the social network– defining book The Dragonfly Effect. Redlitz’s longtime buddy, hip-hop icon turned angel investor MC Hammer, has put in multiple appearances.

Redlitz also encourages participants to become instant social media junkies: They are required to tweet and blog regularly and to answer questions about prison life on Quora’s public forums—things like “What does it feel like to murder someone?” and “Are people born criminals or does society make them so?” The men scribble posts on paper and “tweet sheets” for volunteers to input because inmates are not allowed to use the Internet. Most of them have been incarcerated since before the web went mainstream and have never even been online, much less on Tumblr or Reddit.

To graduate from the program, the inmates have to come up with a fleshed out plan for a business startup. Redlitz encourages the men to mine their personal lives and passions for their business ideas; the projects must also incorporate technology, social media, and social benefit. Half a year after the inmates first set foot in the program, they present their ventures at a classic, incubator-style Demo Day to an audience of investors and tech leaders—the first one, in May 2012, attracted an audience of 40 (including Jerry Brown’s wife, Anne Gust Brown); by the next one, the crowd had grown to 100. The program’s mission is to train entrepreneurs and coders in prison and then provide them with jobs (or, better yet, the skills to start their own businesses) when they get out. If any of the ventures hits the jackpot, the goal is to plow the profits back into the Last Mile, funding more training and more jobs and more entrepreneurs, which would then feed the next cycle of inmate trainees. But Redlitz isn’t assuming that this will happen very often, if ever: “I don’t expect all of the ideas to become businesses,” he says. “I expect that all the guys who go through this program will enter the workplace more educated and confident.” Still, he proudly touts one investor’s response to a presentation at last year’s Demo Day: “If that had been at Y Combinator,” the investor told Redlitz, “it would have been funded.”

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