Silicon Valley Meets San Quentin At The Last Mile Demo Day

[Updated 7/27/12 with a new video—see page 2] The next time you feel like complaining about your startup job, take a second to imagine would how much harder it would be if you were behind bars at San Quentin.

Lest you think I’m pulling this comparison out of thin air, read on. Last week, in an unprecedented ceremony inside the walls of the notoriously crowded state prison in Marin County, five inmates and one former prisoner marked the completion of The Last Mile, a nine-month program designed to prepare them for employment in the Silicon Valley technology world after their release.

These men aren’t allowed to run businesses from inside the prison. They don’t even have direct access to the Internet, let alone smartphones or any of the other gadgets or services transforming the world outside the walls. But as Last Mile participants, they were required to learn how modern computing and communications technologies work, develop business plans for their dream companies, and finally pitch their ideas to an audience of investors, businesspeople, and government officials at a climactic demo day.

In their presentations, the participants showed the kind of dedication and quick thinking that any startup founder would want to see in an employee—or that any investor would want to see in a founder. And they’ve found this focus in the face of remarkable adversity, both in their personal pasts and in the prison environment. “There is talent behind the walls,” says Chris Redlitz, the San Francisco-based venture investor who co-founded the program. “You just have to find it and nurture it.”

The Last Mile's inaugural class and founders. Left to right: Tulio Cardozo, E. "Phil" Phillips, James Cavitt, David Monroe, Chrisfino Kenyatta Leal, Beverly Parenti (co-founder), James Houston, Chris Redlitz (co-founder)

At Redlitz’s invitation, I drove to San Quentin last Friday for the inspiring and occasionally emotional ceremony, which took place in the prison’s large Protestant chapel. Attending alongside the 40-some investors and entrepreneurs were Matt Cate, Secretary of the California Department of Corrections and Rehabilitation; Anne Gust Brown, wife of California Gov. Jerry Brown; and about 60 onlookers from the prison’s general population.

Needless to say, this was unlike any other startup event I’ve witnessed. To start, those of us visiting the prison had to leave our laptops, phones, and cameras at home. We were allowed to bring only our car keys, driver’s licenses, notebooks, pens, and business cards. As we walked single-file through the facility’s forbidding, castle-like maw, we signed a logbook, had our wrists stamped with ultraviolet ink, and passed through a pair of clanging security gates.

Then there were the presenters, who weren’t your typical crew of fresh-faced young entrepreneurs. James Cavitt, 33, is serving 25 years to life for a home invasion robbery. He was convicted at age 17. James Houston, 38, is serving 15 years to life for a drug-related murder. Chrisfino Kenyatta Leal, 43, got an indeterminate sentence under California’s three-strikes law as an ex-felon in possession of a firearm. David Monroe, 29, is serving 15 years to life for a gang killing. He was convicted at age 15. E. “Phil” Phillips, who is in his early 40s, has served 17 years of a 38- to-life sentence for second-degree murder.

A sixth member of the founding Last Mile class, Tulio Cardozo, is a former San Quentin inmate who finished his sentence and has since been helping Redlitz and his co-founders, Kathleen Jackson and Beverly Parenti, to administer the program. The ceremony marked Cardozo’s first time inside the facility since his release. (As we were waiting outside the prison gate, I asked him what it was like being back. “It probably won’t sink in until I’m past these doors,” he said.)

Once the introductions and speeches were out of the way, however, the presentations from Last Mile participants were as smooth and upbeat as anything you’d see at a Silicon Valley demo day, spanning markets from clothing to hair care to digital music and home entertainment.

It was the culmination of a lot of hard work. Since September, Redlitz said, the men have been reading business books, learning computer and software skills, meeting with outside mentors, formulating ideas for the businesses they’d like to run, practicing their elevator pitches, and polishing their PowerPoint decks.

The big difference between The Last Mile and a typical accelerator, of course, is that the participants who are still inmates won’t be able to start building or testing their actual products until they get out. For most of these men, parole is still years away, and some have no definite release date.

“Not all of these ideas will see the light of day, but what we asked them to do is think big,” Redlitz told me the day after the event. “I had an investor who was there e-mail me, saying he loved [Leal’s pitch]. He said ‘If that had been a Y Combinator presentation, it would have been funded.’”

Four of the six presentations were off the record, given that it’s unclear when, or if, the ideas will get off the ground. But Cardozo’s startup, called Collaborative Benefit, is already in development, and James Houston’s company, Teen Tech Hub, is set to open in 2013.

Like all of The Last Mile projects, these two efforts have technological components, but they also address social causes. Cardozo is taking on a problem that hits close to home: the high unemployment rate among former prisoners. “There are 2.3 million people in prison in the United States, including 137,000 in California,” Cardozo pointed out in his presentation. “Most of us will get out, but only half of us will get a job.

Collaborative Benefit plans to offer a free online service that will help employers evaluate former prisoners as potential employees. Taking inspiration from LinkedIn, the service is designed to showcase members’ talents and accomplishments through online profiles, social media updates, and video interviews. Applicants will be screened before they’re listed, and will get help finding full-time or part-time positions that match their skills.

Cardozo said that as the program matures, men who have already found employment through the program will be called upon to counsel incoming participants. “Our graduates will become lifers in a different way,” he joked. Among the first companies to sign up are BTS Communications, an advertising and social media agency housed within a Los Angeles drug treatment center, and Dave’s Killer Bread, an Oregon-based breadmaker founded by former convict Dave Dahl, who attended last week’s ceremony. It’s expected to go live on the Web soon.

Houston’s organization, Teen Tech Hub, will be an after-school technology training program aimed at pre-teens and teens in minority communities. In California, 58 percent of 9th graders in minority schools don’t go on to graduate, often because they lack social support from adults, Houston said in his presentation. “Think about the most important people in your world growing up,” he said. “Now think about the world without them.” That’s the world most of the kids in Teen Tech Hub’s target market inhabit, he said.

The program will be a “safe haven” between school and home where youth can get advanced software training for up to two hours each day and join classes that meet twice a week, Houston said. Financial support will come from corporate sponsors, and Teens in Tech, a Mountain View, CA-based entrepreneurship program for teens, will run monthly seminars on coding, marketing, and design. (Daniel Brusilovsky, the founder of Teens in Tech, was one of the Last Mile program’s volunteer mentors.) Houston himself will be eligible for parole in 2013.

It was meeting Houston, Redlitz says, that sparked the idea for the Last Mile program more than a year ago. He’d been invited inside San Quentin by Kathleen Jackson, a former teacher and school administrator who has spent five years volunteering at the prison, most recently as an advisor to an inmate group called T.R.U.S.T. (Teaching Responsibility Utilizing Sociological Techniques). “I went to a T.R.U.S.T. graduation, and they had food afterward, and we sat with seven of the men including James Houston, and I was really intrigued by him and his story,” Redlitz says. “A month later I came out and did a short program on entrepreneurship. The response to that was so overwhelming that I really started thinking about what we could do.”

The main argument for programs like The Last Mile, Redlitz says, isn’t a sentimental one or even an ethical one; it’s an economic one. Incarceration costs $50,000 per inmate per year, and the budget for California Department of Corrections and Rehabilitation is almost $10 billion. That’s 30 percent more than the state spends on education. Yet the department is clearly struggling with the “rehabilitation” part of its mission: the recidivism rate for released prisoners is 70 percent. “That is a bad investment,” says Redlitz, who also runs the Kicklabs accelerator program in San Francisco. “That is what motivated me first. Also, I have some resources, and I thought I could create something that would start small and see if it would resonate.”

There’s no question that it has resonated, at least with the six members of the initial Last Mile class. Inmate David Monroe told me that before The Last Mile, he’d never even heard of modern conveniences like QR codes, which now figure prominently in his business plan. With help from the Last Mile volunteers and from each other, he said, the participants have gained the confidence to succeed in the world after their release. “I committed murder. Society judges us for our worst actions,” Monroe said. “But so many of the inmates are like us. They want to do better. It’s great to know there’s hope, even for the worst of the worst.”

Monroe, by the way, is one of the Last Mile participants who have become minor Internet luminaries through their posts on Quora and Twitter, mostly pertaining to life inside San Quentin. Marc Bodnick, a former private equity investor who now runs product marketing and businesss operations at Quora, said at the ceremony that the Last Mile participants’ posts stand out because of their authenticity and thoughtfulness. “On our site these guys are celebrities; nobody gets up-voted faster,” he said. “What the Last Mile folks have done is shine a light on a world most of us don’t know very well.”

Cavitt, another prominent Quora contributor, provided perhaps the most poignant moment at the Last Mile ceremony in a spoken-word performance of a poem he had written. It was about his development from a lost young offender into a wiser, older man. “I am not my worst decision,” Cavitt said. “I had to stop screaming in order to start living.”

And that may be the biggest argument for The Last Mile, which Redlitz hopes to expand to a larger group of inmates at San Quentin and other prisons in California. Whether or not any of the program’s participants become Internet tycoons, they’re building on their talents and looking for ways to give back to society. The Last Mile program can “help bridge the gap between incarceration and freedom, if you put in the work,” Jackson said at the ceremony. “These men have put in the work.”

Update 7/27/12: Here’s a video recorded at the Last Mile demo day.

Wade Roush is a freelance science and technology journalist and the producer and host of the podcast Soonish. Follow @soonishpodcast

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