Nonetheless, the program, launched by successful tech entrepreneurs for inmates north of San Francisco in the decaying San Quentin State Prison, has expanded, and a new session began this month in the gritty, downtown Los Angeles Twin Towers Correctional Facility.
The reason they're growing is simple: Graduates, now trickling out of the penal system, are landing real jobs at real dot-coms.
The rigorous, six-month training teaches carefully selected inmates the ins and outs of designing and launching technology firms, using local experts as volunteer instructors.
"We believe that when incarcerated people are released into the world, they need the tools to function in today's high-tech, wired world," says co-founder Beverly Parenti, who with her husband, Chris Redlitz, has launched thriving companies, including AdAuction, the first online media exchange.
The pair were Silicon Valley pioneers in the 1990s, and they tap their many high-level connections to help with the prison program they started the program after Redlitz was invited into San Quentin in 2011 for a guest lecture and was overwhelmed by the inmates' desire to learn.
"I figured, 'We work with young entrepreneurs every day. Why not here?'" he recalled.
After discussions with prison administrators, Parenti and Redlitz decided to add a prison-based firm to their portfolio, naming it for the precarious journey from prison to home: The Last Mile.
Now, during twice-a-week evening lessons, students many locked up before smartphones or Google practice tweeting, brainstorm new companies and discuss business books assigned as homework. Banned from the Internet to prevent networking with other criminals, they take notes on keyboard-like word processors or with pencil on paper.
The program is still "bootstrapping," as its organizers say, with just 12 graduates in its first two years and now a few dozen in classes in San Quentin and Twin Towers. But the five graduates released so far are working in the tech sector.
They are guaranteed paid internships if they can finish the rigorous training program, which requires prerequisite courses, proven social skills and a lifetime oath to lead by positive example.
In one recent class, while thousands of inmates exercised or played chess in San Quentin's prison yard, students worked their way through a business model, pitching different technology concepts.
"What are the distribution channels?" challenged seminar leader Andrew Kaplan, a product marketing manager at LinkedIn. "What platforms or networks do we need to think about? Who are we trying to engage?"
Tommy Winfrey, 35, who is serving 25 years to life for second-degree murder and hopes to be paroled in 2018, adjusted his eyeglasses and raised a tattooed arm. "I think an important part of our brand is going to be to give our customer a voice," he said, suggesting they share ideas on social media.
On a Silicon Valley-style Demo Day, the startup students present ideas to investors, a demonstration that convinced former California Department of Corrections and Rehabilitation director Matthew Cate he made the right decision to approve the training course.
"This program will go a long way to not only providing these guys with jobs, but it is my hope that they hire people like them who have changed their lives and are now ready to contribute to society, pay taxes, follow the law, support their families. All those things contribute to the economy," he told participants after watching the 2012 Demo Day.
Inmates also learn the essential startup skills of blogging, in part by answering questions on Quora, a website that allows users and experts to communicate, by having volunteers input their entries. Without real businesses to discuss, thousands of readers ask the inmates questions such as: "What does it feel like to murder someone?"
"Murdering someone was the ultimate release for me," blogged David Monroe, 30, who killed a 16-year-old when he was 15. Over the long term, he added, the murder "has forever pitted my heart with regret and covered it in shame."
Writing publically about their crimes, organizers say, helps the inmates move forward once they are released.
Just months after serving 24 years for repeat drug offenses and weapons possession, Chrisfino Kenyatta Leal fed his cat and ironed his shirt before hurrying off to catch a Bay Area Rapid Transit train in to his office in San Francisco.
"I always had an entrepreneurial fire in my belly, I just used it in the wrong way," said Leal, 45.
Like the other entrepreneurs hurrying to meetings, tapping on computers and talking on smartphones at startup RocketSpace, Leal has a passion for technology and the possibilities it holds.
He just acquired his skills in a very different classroom.