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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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For most of the last eight and a half years, Heracio “Ray” Harts’s daily uniform was dark pants and a short-sleeved blue shirt emblazoned with the words “CDCR Prisoner.” He spent his days packaging test tubes as part of a San Quentin joint venture with a medical supply company, his evenings sitting on a bucket reading in the 6 1/2-by-12-foot space he shared with his “celly” or in a classroom studying for his college degree. The thing that defined him—to the world, if not to his family and friends—was the crime he committed on a Friday night back in 2004, when he shot a man outside a friend’s house in Stockton. “I killed someone, a father, with kids,” he says. “It’s something I’m very remorseful about. You don’t forget what you’ve done. You try to make things better.” But as much as Harts was determined to do that—to leave prison a better man, to take care of his wife and kids, to make a positive contribution to his community—he knew the road ahead would be long and arduous. Both his brother and his uncle were serving time alongside him in San Quentin; many of his childhood acquaintances were in prison as well. “I would lie in my cell worrying about the future,” he recalls. “I was sure that no one would ever hire me.”

Harts had seen it happen many times before—a guy would leave San Quentin and get lost. The label of ex-con is almost impossible to shake, and most former inmates in California can’t do it—within three years, nearly two-thirds are back in jail in a cycle that repeats throughout their lives. For those newly out of prison, work that pays a living wage is hard to come by; basic support services such as job training and substance-abuse treatment are virtually nil. The California prison system, the 11th largest in the world, is more concerned with retribution than redemption, ensuring that it’s not just criminals who are punished, but also the families and communities to which they return when their sentences are complete. “You’re stereotyped and you’re stigmatized,” Harts says.

Yet one morning in May, 63 days after walking out of one of the country’s most infamous penitentiaries, here is Harts, dimpled and upbeat, giving a presentation at the sleek Mountain View offices of Quora, the crowd-sourced question-and-answer website cofounded by two former Facebookers. Nothing about his appearance suggests his former life except maybe his bulging arms and barrel chest, the product of prison-yard bench presses done with makeshift weights—garbage bins filled with water. Today he is looking exceedingly sharp in a pinstripe button-down; the prison braids have been buzzed into a neat, close crop. Against all odds, Harts has morphed into an aspiring entrepreneur and eager-to-please paid intern at, the crowdfunding-for-activists site in San Francisco. Now he’s at Quora to pitch his first Rally project—“Paving the Road to Success,” he calls it—which seeks to raise $5,000 to provide basic necessities for his fellow parolees, supplementing the paltry $200 in “gate money” that they get from the state.

Harts is nervous, not least because his son—11 years old when Harts went to prison, now 19 and the freshman class president at Clark Atlanta University, where he is putting together his own talk show—is here to cheer him on. Until a few months ago, Harts had barely ever been online, and now he’s speaking to a roomful of engineers, coders, and marketing types with fancy degrees and unmatched technical expertise. He has their sympathy, but he wants their respect. Ultimately, respect for who he is and what he’s trying to accomplish is what will fuel their desire to help him and other former inmates who dream of turning their lives around by working in tech. “Most people don’t have the support I have had,” Harts tells them. “Please give so I can pay forward the opportunity I was given.” The audience, a sea of faded T-shirts and sloppy jeans, is rapt, nodding and smiling, even if, in the end, their donations come up short of Harts’s $5,000 goal.

Also standing up front is Chris Redlitz, Harts’s mentor and a veteran San Francisco venture capitalist whose beaming face could light up a small town. Redlitz has been working with Harts for a year now through the Last Mile program—a new rehabilitation model that’s one part startup incubator, one part job-training course for inmates, and one part wild reimagining of the prison-industrial complex. Harts “is very thoughtful and heartfelt about what he says, and I think that’s what’s so compelling about him,” Redlitz says. “His confidence has increased dramatically.” Redlitz is equally effusive describing Harts’s success at Rally. “He’s absolutely immersed himself in learning.” Harts isn’t the only Last Mile alumnus in the room: In the back, Tulio Cardozo, who served nearly eight years in prison for manufacturing hash oil, is running the slides for Harts’s presentation; six months out of San Quentin, he has his own consulting business creating sites on WordPress and Drupal. Back at the prison, three more Last Milers are on the verge of being released. To Redlitz, Harts and the others aren’t just a feel-good story; they’re a proof of concept, an example of how tech might be harnessed to help solve one of California’s most daunting long-term problems—the reintegration of the state’s vast prison population into productive society—and not a moment too soon.

Every day in this country, 1,600 inmates walk out of prison and back onto our streets and into our communities. This endless flood is the result of a staggering incarceration boom: In 2011, the United States had 1.6 million inmates, five times more than in 1980. If the current incarceration rates persist, 11 percent of boys born in 2001—and 32 percent of African-American boys—will serve prison time, the U.S. Department of Justice predicts. Eventually, 95 percent of them will be released back into society. The answer to the question “Then what?” has eluded our nation for decades.

California has the dubious distinction of being a leader in this boom: During Governor Jerry Brown’s first administration, the state had 44,000 prisoners; today, it has more than 42,000 prison employees and more inmates—133,000—than any state except Texas. California has also failed monumentally at figuring out what to do with inmates once they are released. Within three years, 63.7 percent of the state’s ex-cons are back behind bars, one of the nation’s highest recidivism rates. That statistic is hardly surprising given that just 4 percent of California’s $8.9 billion corrections budget goes toward rehabilitation and that only 14 percent of inmates participate in vocational or education programs while behind bars. Add the fact that the men and women who move through California’s prisons and jails read, on average, at the seventh-grade level; that just half of them ever held a job before incarceration; and that 65 percent of employers indicate that they would not knowingly hire a felon, and you have the makings of a new type of unemployment epidemic: the unhireables. And that dismal outlook doesn’t even take into account the lingering effects of the recession and the Supreme Court–ordered “realignment” initiative that is forcing California to deal with massive prison overcrowding by putting more inmates on the streets.

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