Inmates at work on computers at San QuentinRobert Galbraith / Reuters

On the fifth floor of Slack’s new building, overlooking the fancy Salesforce Park, a standing-room-only crowd of employees had gathered. Almost universally young and San Francisco casual, but not universally white and male, they were there to see John Legend, and to celebrate Next Chapter, a new partnership the chat start-up has entered into with The Last Mile, a technology-training program for incarcerated people, and $800,000 from the W. K. Kellogg Foundation.

Next Chapter will train and place three “returning citizens” inside Slack as quality-engineering apprentices—and build a process to help them acculturate to one of the most successful start-ups of the past decade, with help from a small support team led by a formerly incarcerated man named Kenyatta Leal. The apprenticeship is split into three parts over a year: Roughly four months at the start-up bootcamp Hack Reactor, four months of training, and then four months on the job, after which Slack may hire an apprentice, or help them get a job at another tech company. Everyone involved with the program seems to believe that if they can make the proof of concept work at Slack, other companies in technology and far beyond might also begin to hire more men and women who’ve paid their debts to society.

The Slack staff knew about this effort, and whether it was the program, the celebrities, or it being a Thursday afternoon—the slot in the week when Slack hosts “gather hour,” its more inclusive, less drunk spin on happy hour—the room felt like a high-school auditorium before a pep rally. The celebrities appeared and a raucous wave of applause overtook the crowd as Legend, Leal, the comedian Robin Thede, and Slack’s CEO, Stewart Butterfield, took the stage.

Butterfield is small in stature, with brownish-reddish hair and glasses. His shirt read We Are All Dreamers. If you’re used to Elon Musk’s bombast, Mark Zuckerberg’s cheery will to power, or even garden-variety start-up boosterism, Butterfield is refreshing and strange, having retained some of that ’90s internet funk. He is the kombucha of tech CEOs.

Like a good CEO, he began by thanking the partners in the program. They beamed from the front row: Chris Redlitz and Beverly Parenti, the founders of The Last Mile; along with Kellog’s contingent, CEO La June Montgomery Tabron and the grant maker Cynthia Muller. (Legend’s criminal-justice-reform organization, Free America, is also on board.)

But before the celebration could even get underway, Butterfield said, “The bigger issue is bigger than us and the things we’ll be talking about today.” He described seeing Bryan Stevenson, the founder of the Equal Justice Initiative and the author of Just Mercy, and being changed by him. “Holy shit, he’s a powerful, powerful speaker,” he said. “That was the year that everyone got Just Mercy as a Christmas present.” That was two and a half years ago. Butterfield visited The Last Mile at San Quentin and came away thinking Slack could make a difference working with them.

Now more than 100 Slack employees have visited San Quentin to meet and mentor people enrolled in The Last Mile’s coding program. And Butterfield offered up his company as the test case for getting prison-trained coders into high-growth start-ups, something that has not really worked yet.

“I don’t want to say this is it. This is a very experimental approach and obviously we hope the experiments work,” he said. “But even to the extent we are successful, which is providing pretty amazing opportunities for a relatively small number of people, we need to create a larger number of opportunities for people. I say we, but I mean us, the country.”

More than 20 percent of the whole world’s prison population is sitting in U.S. jails and prisons, even though Americans make up only 5 percent of the world’s population. The country, I mean us, has been terrible at providing opportunities for people leaving prison. The formerly incarcerated are five times more likely to be unemployed than the general population. Things are especially bad for black men, who experience significantly higher unemployment than white men leaving prison.

There is no single reason for these dismal statistics, but the Annie E. Casey Foundation summarized some of them: difficult and time-consuming probation requirements, financial debts awaiting people returning home, state laws that keep people with convictions from certain jobs, underfunded prison-education programs, and a lack of recent employment experience. And then there is employer intransigence. One survey of 3,000 employers found that two-thirds of them would not knowingly hire someone who’d been in prison.

“We’ve come up with thousands of ways that a plastic bottle or an aluminum can can have a new life,” Leal explained to the crowd. “We need to have that same kind of mind set when people return to the community.”

Right now, though, “it’s an obstacle course,” Legend said on stage. “You can’t get housing access if you have a criminal record. There’s the employment issue. If you can’t get housing and a job, that is your life.”After a half hour of conversation, Legend took the piano and played his old hit “Ordinary People” and the anthem of his organization, Bob Marley’s “Redemption Song,” to back-to-back standing ovations.

For those assembled, it was clearly a thrilling, inspiring event. But at the end of the day, this program won’t be judged by whether the engineers in the room had a good time, but whether Next Chapter can, unlike previous efforts, actually launch formerly incarcerated people into the technology industry. Is all this a real step forward or a distraction from more pressing prison reform and reentry work?

Slack CEO Stewart Butterfield (left) and Kenyatta Leal of Next Chapter on stage (Russell Shaw)

Offstage, the heavy lifting for Next Chapter has been done by The Last Mile (TLM). Founded as an entrepreneurship class at San Quentin, TLM has grown into a large prison-education program, spread out over eight facilities. The requirements for entry into the program are stringent—no participant can have a disciplinary infraction for 18 months before they apply—and any issue can get them booted. To date, 50 TLM graduates have reentered society and not a single one has returned to prison. (In California, about 65 percent of people who leave prison return within three years.)  

TLM’s mission is to teach imprisoned people to code, which is no simple feat, because there is no internet access inside the walls. They’ve had to build an entire curriculum just for the local network, built on top of the “learning management system” Canvas. And over the past few years, The Last Mile entered into a joint venture with the California Prison Industry Authority, called TLMWorks, which is an actual development shop at San Quentin. “We have a lot of work in the pipeline and we are branching out beyond front-end software development,” Parenti, one of TLM’s founders told me. “We’re doing [Quality Assurance], mobile QA, accessibility QA.”

Many jobs in prisons pay literal pennies an hour. Right now, prisoners across the country are striking to protest “modern slavery.” TLMWorks developers earn far less than they’d make on the outside, but they do get a state-mandated $17 an hour. And the work experience is substantially more valuable than making license plates or manufacturing furniture. It’s enough money—even after the many ways the state garnishes these wages—that many TLM participants have been able to save for their post-release lives.

Aly Tamboura went through the TLM program, start to finish. He loved it. “I’m a math nerd. I took Calculus 1, 2, and 3 for fun and the guys made fun of me,” he told me. “I’m going to try this computer coding.”

He said that coding gave him a sense of purpose. Not only was he working on something he found intellectually satisfying, he was learning “a marketable skill” that could pay him enough to actually support a family and live in the Bay Area. He worked on product development for two years. “It is a real software-development shop. We have 15-minute stand-ups, we do paired programming, we do code review,” he said. “When I got out here, it was everything I’ve already done. ‘Oh there’s a stand-up meeting?’ Using Github, using Trello. It really prepared you.”

While Tamboura was inside, Butterfield came to visit. The inmate had just built an application for the University of Pittsburgh, and Butterfield was impressed. “He was really amazed that incarcerated people were able to produce this kind of technology,” Tamboura said.

When he got out, Tamboura wanted to keep going down the developer path, but felt like he needed some classes on the outside to be competitive in the job market. He set his sights on a coding bootcamp called Hack Reactor. Butterfield heard about it, and Slack sponsored Tamboura and gave him a monthly stipend.

It wasn’t easy work. “I struggled through Hack Reactor. I think I was 49 or 50 at the time and there are a bunch of 20-something kids who just graduated with computer-science degrees,” he said. When he finished the bootcamp, he started getting calls from recruiters and even offers from other companies like Adobe. But Slack had sponsored him, so he interviewed with the company. But then, he said, “I got a technical assessment and flubbed it.”

Even though Tamboura ended up with a job doing criminal-justice reform at the Chan Zuckerberg Initiative, the people at Slack were crushed. They’d wanted Tamboura to work out. The Last Mile, for its part, has had very few of its graduates actually go on to land coding jobs. How many? “Probably a handful” out of the 50 graduates who have returned to society, Parenti told me.

So it made sense to both parties to invest the resources to figure out how to build a functioning pipeline for people coming out of prison into Slack. “How do we do this right, not in a one-off way?” said Deepti Rohatgi, Slack’s head of company affairs and “Slack for Good,” told me.

That’s when Slack reached out to Kellogg for its expertise in racial equity. Black and brown (but especially black) people are locked up at far higher rates than white people.“Incarceration, in some ways, that’s a symptom,” said La June Montgomery Tabron, the CEO of the Kellogg Foundation. “The more fundamental issue: racial inequality and racism.”

Slack also coordinated with The Last Mile to ensure that students’ learning would mirror the actual work of a start-up, and started to navigate some choppy regulatory waters. “There are a lot of restrictions about what people with felonies can touch with regard to customer data,” Rohatgi said. “We were able to find a role for them that is technical and very important to Slack, but allowed us to follow the law.” Then—because there’s quite a difference between being politically opposed to the prison system and being open to sitting next to someone with a conviction for armed robbery on his record—Slack gave trainings to managers, invited Tamboura to speak, had one-on-one meetings with Leal.

“There definitely was some fear, and I think that is perfectly understandable,” Rohatgi said. “But we’ve gone from that to people are just damn excited about this program.”

Leal might be the most excited. He’s come a long way personally and he’s ready to scale his success. “We’re partnered with Slack, but if we can get five more companies, we can get 10. If we get 10, we’re going to get 100. If we get 100, we can get 500,” he said. “I can see it snowballing.”

The most obvious critique of the program is that it is just small: three guys, when California alone has roughly 115,000 prisoners. But that’s not the only one. Offering an apprenticeship rather than a permanent job may not seem like a huge distinction, but multiple advocates for formerly incarcerated people called attention to this part of the program design.

“I think it’s all a great idea in concept, and I’d love to see the end result,” said Pat Mims, who was incarcerated for 20 years and is now the director of the Reentry Success Center. “The end result is getting guys employment—and not just employment, but careers in the field where they are working. To train them and have them ready for work but not be able to get them a job in the field they trained for is concerning to me.”

That’s not exactly how Slack’s Rohatgi sees the program’s goal. She said that the apprentices don’t need to end up at the company for the program to be a success. “Of course, they’ll get an interview at Slack,” she said. “But success to us doesn’t necessarily mean they join Slack, it means they are successful within technology and in their communities.”

Carmen Rojas, the executive director of The Workers Lab, which invests in organizations that empower workers, shared Mims’s concern that an apprenticeship is not guaranteed employment. And, of course, working on this scale, the program cannot address the deep causes underlying mass incarceration. “The challenge with this program is that it places a burden on returning citizens to navigate training systems without guaranteeing employment or addressing the systemic causes of poverty that can lead to incarceration,” Rojas told me in an email.

Tamboura thinks that the apprenticeship program can and will evolve toward guaranteed employment. “I’d like to see the internship thing go away, and I believe that it will go away as the guys run through the program and the [company] sees this is a precaution they didn’t need to take,” he said.

If Tamboura’s critique is that the program is not optimistic enough, some reentry activists worry that The Last Mile’s—and tech’s generally—ideas for helping are a waste of resources. The fact of the matter is that the vast majority of the people leaving prison will not get tech jobs. Would it be better to spend the money Slack is using on this program elsewhere, helping people simply pay their bills by getting jobs at warehouses or in food service? Delancey Street Foundation trains formerly incarcerated people in food-service work, and helps get them jobs. Could Slack or Google push on their food-service contractors to hire from Delancey Street to generate more jobs?

They could, but they shouldn’t stop there, said Mims.

“Delancey Street does what it does because the food industry hires formerly incarcerated people. There’s a track record,” he said. “We’re trying to break a track into the tech world, where everything is headed … Yes, they can use their power in their way, but we’re getting away from the main objective. That’s to get them in the tech field, not to work in the the tech world’s cafeteria.”

Of course, money for reentry services and to address to root causes helps, too. Google has given $32 million in philanthropic contributions to different criminal-justice organizations, and sponsored a series of events around the topic. It was also the first major tech company (in 2011!) to stop asking about criminal history on its initial employment application.

Facebook’s Mark Zuckerberg has visited San Quentin, where he met with Tamboura and The Last Mile. He referenced Michelle Alexander’s book The New Jim Crow in a blog post about the need for criminal-justice reform. “We can’t jail our way to a just society, and our current system isn’t working,” he wrote. Zuckerberg’s social-good organization, the Chan Zuckerberg Initiative, has also committed tens of millions of dollars to criminal-justice reform.

But reform advocates point out that reentry is a brutally difficult problem, and more than dollars are necessary to change the system. Those dollars have to go to the right places.

“Very few prisoner-reentry programs have proven effective,” said Michael Romano, the director of the Three Strikes Project at Stanford Law School. “If tech companies and leaders really want to help address one of the major social challenges of our time, they can—and should—devote their considerable resources and analytical expertise to figuring out which programs work, and which don’t, and encouraging and developing those that are most effective at addressing the astronomical problems we face.”

If Butterfield has his way, many more tech CEOs will see the urgent need for prison reform that touches their actual companies. “We give an example and the blueprint, letting people know that it is possible. We give gentle encouragement all the way to public shaming,” Butterfield told me. “It’ll happen. Who wants to be the last CEO to participate in this program?”

He’s already executing on this plan. After the all-hands event at Slack, Butterfield set up a dinner with a dozen or so A-list tech CEOs to discuss what they were doing to help formerly incarcerated people. “There is a high degree of receptivity,” he said. But he pulled out all the stops to get people there, too. Legend would attend, of course, and dinner would be cooked by Samin Nosrat, the chef and author of Salt Fat Acid Heat (soon to be a Netflix show).

And if the tech companies decide that formerly incarcerated people are good to hire, maybe then some of the stigma that people returning home face will lessen. Butterfield knows that Slack and tech apprenticeships can’t match the scale of mass incarceration, but he sees Slack’s work as part of a greater shift that’s occurring around the criminal-justice system.

“That mind set will shift over the next decade or two,” he said. “People will say, ‘Why the fuck did we lock up this many people? Why did we have mandatory minimums or the three-strikes law?’”

Some powerful forces have to bend the arc of history, though. Tech companies did not make the problems of mass incarceration, but they benefit tremendously from the economic system that created the tremendous inequality that has, in part, driven it. It might be fitting if part of the way tech repaid its debt to society was by hiring people who’d already done so themselves.

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