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The Inmates and the Entrepreneur

Diana Kapp | August 28, 2013 | Story Tech World

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.

Page two: "If that were at Y Combinator, that would have been funded."

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.”

Page three: Not searching for a caling

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

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

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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