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  … Next Page »

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

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