With Quora, San Quentin inmates freed from social media lockdown

Inmates participating in the Last Mile program listen as Andrew Kaplan, a product marketing manager at LinkedIn, leads a session of the Last Mile at San Quentin State Prison in California. Inmates taking part in the program are also able to participate in the online question-and-answer service Quora.
(Eric Risberg / Associated Press)

SAN FRANCISCO -- How do new inmates cope with the lack of privacy in prison? What advice would an inmate give someone facing a long prison sentence? What are the effects of incarceration on inmates’ families?

All good questions, none of which had good answers online -- until recently.

Through a partnership with the Last Mile, a high-tech incubator at San Quentin, question-and-answer service Quora has made it possible for inmates to make their voices heard on social media. Inmates who are not permitted to use the Internet write down their answers for volunteers to post on Quora.

Former San Quentin inmate James Houston, 40, says being able to express himself on the question-and-answer service helped him get through some rough times in prison. He answered all three of the questions above -- and then some.


Houston is a graduate of the Last Mile, which helps prepare inmates for a new life outside San Quentin. He just finished a four-month internship with San Francisco payments startup Ribbon.

He’s also focused on building the idea he presented at the Last Mile’s Demo Day last February: an after-school program for at-risk youth in Richmond, Calif. He hopes Teen Tech Hub will steer young people away from the bad choices he made.

“I want to give them the confidence, skills and resources to do something positive in their communities,” Houston said.

Quora has been a way for Houston to share his vision and reach out to the world.

In answering the question, would prisoners make good entrepreneurs, Houston wrote: “Prisoners have used many business skills in their criminal enterprises and do not realize it. Most men have never thought about how they possess some positive skills and gifts which we chose to use in a negative way. … Once you encourage men who already think outside the box to do so for the benefit of society, I believe that you will find your next Steve Jobs or Mark Zuckerberg.”

On whether other men can follow in his footsteps by taking part in the Last Mile, Houston wrote: “As far as the talent pool goes, I agree with a man who said ‘Prison is one of our state’s most untapped natural resources.’”

Volunteers post inmates’ tweets to Twitter too. But Quora has become a popular medium for self-expression -- and social connection -- for inmates.


Quora executive Marc Bodnick said he leaped at the chance to have inmates write answers for Quora after having coffee with the Last Mile co-founder Chris Redlitz.

“This is super exciting for us because one of Quora’s great strengths is sharing knowledge with the world that people wouldn’t otherwise know about,” Bodnick said.

“Being in prison is obviously an experience most of us don’t have. It’s hard to understand what it’s like or to have empathy or to understand the lives these folks lead. We have just given these guys an audience like any other person on the site who writes well. And when you read what they write, it’s really incredible. They write about their lives before going to prison, their lives in prison. Some of the stories are heartbreaking. These are just great, authentic, honest writers.”

The responses from the Last Mile inmates have been so popular on Quora that one of them, from Kenyatta Leal, won a Shorty Award in April before he was released from prison. He filmed his acceptance speech from the prison yard.

Leal, 45, was a three-striker serving 25 years to life for possession of a firearm. On July 3 he was released from prison after serving 19 years. Two weeks later he started working as a paid intern at RocketSpace, which rents office space to startups. Last month he found out he will be staying on at RocketSpace as a full-time employee working in customer operations.

Leal, who helped launch the Last Mile at San Quentin, describes himself as “an aspiring entrepreneur.” He met RocketSpace Chief Executive Duncan Logan while in prison. Logan was so impressed with Leal that in 2011 he told Leal a job would be waiting for him when he got out of prison.


In accepting the Shorty Award, Leal wrote: “When the sponsors of The Last Mile first introduced me to Quora I was skeptical because I didn’t think people would be able to look past the fact that I’m in prison to actually listen to what I had to say. ... It feels really good to know that people are interested in my perspective. Being part of the Quora community fills me with a sense of relevancy that has been missing in my life. Sharing my experience, connecting with others, and being heard outside of these walls is empowering!”