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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 Rally.org with CEO Tom Serres (left) and former communications director Nick Warshaw.
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Still adjusting to life outside prison, Harts is trying to figure out how to pack more hours into his day. “I asked [Redlitz] how much sleep does he get at night, and he said about five hours. I’m getting about six and a half, so I still have room to work harder,” Harts says, laughing heartily. “Chris reeks of success. Without even driving me, he drives me.” We’re in a conference room at Rally, a few blocks from South Park, eating grilled chicken and kale salad and sipping Pellegrino—free gourmet lunch is a perk of Harts’s new internship. So is the onsite yoga session that leaves Harts panting and sweaty. “That class is intense,” he says.

There wasn’t a lot of kale or yoga where Harts grew up—he was raised by a single mom in working-class Pittsburg in Contra Costa County. College, he says, was never in the cards: “My high school counselor never even told me about the SAT.” He started selling drugs as a teen, though he did finish at Pittsburg High, he says, with a 3.2 GPA. After graduation, he found a decent-paying job at an oil refinery to support his new wife and baby son. But the plant closed down—“I remember going over to my mom’s house and crying when the refinery closed,” he says. The financial strain pushed him further into slinging drugs, and his life spiraled downward. As a kid he always assumed that he would do time, the way many middle-class kids assume that they’ll go to college. “I remember I was maybe 8 or 9 years old, and my uncle went to prison, and I was thinking, ‘Well, if I go to prison, I’d be there with my uncle,’” Harts says. “At that age, you shouldn’t be thinking about if you go to prison.”

When I first ask Harts what landed him in San Quentin, he tells me about the drugs and gun possession but omits the key scene in which he shot a man and killed him. In a catch-up phone chat weeks later, he finally discusses the homicide—and the deep regret and guilt that he still feels. “I wish I could take it back. At that moment I wished I could have taken it back.” I press for more information, but he’ll only speak in vague terms, telling me, “I’m really not comfortable about talking about the details of it, out of respect for [the victim’s] family.”

Many marriages have been fractured by far less, but Harts’s wife, LaVonda, stuck by him. When he was released on March 12, she waited two hours at the front gate to meet him, accompanied by their new baby boy (conceived during a conjugal visit) and their teenage daughter and son. Harts finally exited around 7 a.m., wearing a three-piece gray suit that LaVonda had purchased and that, she tells me later, her husband had “specified down to the brown belt and shoes, even the underwear.” Harts believes that practicalities like clothes matter enormously during an inmate’s reentry. “The start of a new chapter began with my clothes,” he says. “If you can look professional, you are welcome in society.”

After the hugs and tears, they piled into the family van. Harts’s son, also named Heracio, took the wheel, which “felt crazy,” Harts says. His daughter handed him an iPod loaded with the songs he had requested for these first moments of freedom. But he had no idea how to work it and handed it back. “I knew he wasn’t going to be able to figure that thing out,” his wife says, laughing. I ask Harts how his kids turned out so well, given the circumstances. “Their amazing mom” is all he says. LaVonda does the explaining for him: “We just took it day by day. I consulted him on every important decision. I gave him that respect.”

Still, even with the Last Mile folks and LaVonda behind him, Harts faced the kind of daily frustrations that make being a parolee so difficult. His family lived in Dublin, but he had to meet his parole officer in San Joaquin County, where the killing occurred, costing him $500 for a hotel that first week. After Redlitz got involved, Harts won approval to live at home and work in San Francisco, with periodic check-ins in Stockton.

The truth is that Redlitz offers all kinds of support to ensure that his guys succeed. He attends parole hearings as a character witness. To make good on his promise of a four-month paid internship for every Last Miler who completes the program, he relies heavily on his vast professional network, including at Rally, where he is an investor.

Even so, Harts had to earn his position at Rally, meeting with eight interviewers, Redlitz says. As Harts describes his first weeks on the job, it sounds more like he’s attending bring-your-kid-to-work day than undertaking major responsibilities. He has listened in on product, technology, and marketing meetings, and he was pulled into a session with Christine Pelosi (Nancy’s daughter) when she came to discuss her new Rally campaign against gun violence. Pelosi requested that Harts join her team, and of course he agreed. The deliverables, one assumes, will come later.

Redlitz is quick to warn inmates that the transition from prison to tech internship is stunningly complex. For Harts, the trickiest part isn’t boning up on basic computer literacy, learning to hyperlink, or sending images in texts—it’s simple time management. For almost a decade, he had a life in which he made zero decisions. “It’s like getting on the freeway again after sitting in the slow lane—actually a parking lot—for so long,” he says. He is clearly feeling uneasy about his productivity (“I haven’t had a lot of time to work on projects because I’m doing interviews, and I get pulled into different meetings,” he laments). But at Rally his work ethic is unquestioned. Even during the four-day BART strike in early July, when most of the company’s East Bay staff chose to work from home, “Ray figured out some crazy two-hour chartered bus route to get here before everyone else,” his boss, Rally communications director Nick Warshaw, emails me. “Just thought I’d share!”

Warshaw was moved to employ a Last Miler after attending the program’s second Demo Day this February—the one in which Harts pitched his Healthy Hearts Institute. “I can’t say there was no trepidation—it’s not a normal initiative,” Warshaw says. “That’s why it’s interesting.” He is impressed by Harts’s “dogged determination,” though he would like to see him be more assertive. “He shows a great deal of deference to my opinion or other opinions. That’s not what works in this environment. He’s gotta lose that,” says Warshaw. “There’s a very conscious piece of him that he’s still a prisoner, and people won’t want to listen.”

Harts isn’t interested in being just a heartwarming anecdote. “I want to add value,” he says. When I ask if he believes that this is happening at Rally, he replies, “Yes, I believe so.” He’s hoping to get out of his Dublin rental and buy a house, maybe take the family to Hawaii. Mostly, though, he’s focused on work. “I’m checking my emails as soon as I get up,” says Harts. “Before he gets up,” his wife corrects. “He rolls over in bed and starts checking email. He’s worse than me.” Harts doesn’t deny it. “I’m really, like, driven right now,” he says. “I want to get things done.”

Page five: Scaling up