Tech Executives Offer Advice For Inmate Entrepreneurs

By Juan Haines Managing Editor

People don’t usually talk about Silicon Valley and the California prison system at the same time. However, on any given day, venture capi­talists as well as business men and women right out of Silicon Valley come inside San Quen­tin to hear inmate ideas from the entrepreneurial program The Last Mile (TLM).

TLM teach inmates how to develop their own business plans and how to pitch their plan to venture capitalists, business executives, public safety personnel and other in­terested parties.

The pitch, given during Demo Day, is also an oppor­tunity for the inmates to net­work and assess the feasibil­ity of ideas they think would solve a problem in the busi­ness world. The next Demo Day is planned for March.

To help facilitate the learn­ing process in the months be­fore Demo Day, TLM spon­sors Chris Redlitz and Beverly Parenti invite business professional inside the prison to give classes on topics such as brainstorming, how to build a company and what kind of ideas attract venture capital­ists.


Last winter when Tina Seelig, author of What I Wish I Knew When I was 20, visited the men, she talked about how to brainstorm for business ideas.

“If you want to succeed, don’t have a fixed mindset,” Seelig said. “Work on chang­ing your position and perspec­tive. Once the right questions are asked, the answers will come.”

She encouraged the men to leave their comfort zones, suggesting that new experi­ences may lead them to new passions. Passion, according to Seelig, is the key to a suc­cessful business.

She also encouraged the group to see every problem as an opportunity.

Seelig’s tips to inmates in­cluded standing up while brainstorming, focusing on one topic, considering differ­ent points of view and using small teams to allow better communication between par­ticipants.


For the last 25 years, Mi­chelle Messina has worked with start-ups in Silicon Valley.

“The job you’re embarking on is really, really hard. The best thing you can do is build a support team,” she said during her visit. “What’s so unique about Silicon Valley is its di­versity in culture. There are 120 different languages spo­ken and about 49 percent of the people are foreign born.”

Messina told the students what to consider when build­ing a company.

“You must think about val­idation in the marketplace. Who is your customer base? You must be solving a prob­lem in the marketplace organ­ically. It’s about knowing your company, and making contact with that customer, and mak­ing the sell in person. Are you solving a problem?”

Messina then listened to some of the men present their ideas and gave advice on where improvements could be made.

Afterward Parenti evaluat­ed each man’s viability as to whether his plan was up to par for the March Demo day.

If the plan was up to par, he was in the Starting Line Up category. If his plan was good, but needed work, he was On the Bench. If the idea itself needed work, he was Not Suiting Up.

Of the 19 participants, five were in the Starting Line Up, five were On the Bench and four were Not Suiting Up. The other five participants did not present their ideas that day.


On the day venture capital­ist Dave McClure came to San Quentin, he listened to some pitches, then said, “When you’re pitching to a venture capitalist, talk about the problem, not the solution.”

“What’s the same about ev­erybody is the optimism of wanting to succeed,” McClure added. “However, out of 100 companies, maybe five to 10 might actually work.”

McClure explained what it means for a business idea to “pivot.”

“Pivot means that whatev­er you build did not work, and you need to change something in your product,” McClure said. “When you pivot, there may be some part of it that is not work­ing and needs to be changed.”

McClure started an investment group called 500 Start Ups. He said the idea is to invest in many companies in order to answer some of questions about what it takes to run a company.

“I may not be in the same po­sition as you guys, but I consider myself an underdog,” McClure said, referring to the ups and downs of his life.

“A lot of people we’re going to invest in aren’t going to make it. However, even the ones who don’t make it are still a part of the community as long as people feel that they’ve got a shot,” he said.

Referring to how the inmates’ pitches sounded, Redlitz said, “You guys were good, but you have to work toward great.”

Said McClure, “People in Sil­icon Valley believe they can do great things. Sometimes, they give advice, something they give money, sometimes they tell you you’re full of it, but that’s help­ful, too.

“Most of my success comes from not giving up,” McClure added.

The Last Mile founder Chris Redlitz addresses the audience during Demo Day in San Quentin, 2014

The Last Mile founder Chris Redlitz addresses the audience during Demo Day in San Quentin, 2014

The Last Mile founders Chris Redlitz and Beverly Parenti (middle) with graduating 2014 graduating class and sponsors

The Last Mile founders Chris Redlitz and Beverly Parenti (middle) with graduating 2014 graduating class and sponsors

MC Hammer address audience and graduates of The Last Mile on Demo Day, 2014

MC Hammer addresses audience and graduates of The Last Mile on Demo Day, 2014


One comment on “Tech Executives Offer Advice For Inmate Entrepreneurs

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