Entrepreneurship Comes Full Circle at The Last Mile in San Quentin

The Last Mile returns to its roots in a new AI-shaped era—launching a reimagined curriculum build to build better futures

In 2010, Chris Redlitz walked through the gates of San Quentin State Prison expecting to give a short talk on entrepreneurship and leave. He was a venture capitalist, a co-founder of Transmedia Capital. Chris had no connection to the justice system. He figured he’d speak for half an hour, shake a few hands, and be home before dinner.

What he found inside changed his life forever.

The men he met weren’t passive participants. They were sharp, prepared, hungry to build something. A few came with business plans scratched in pencil on scraps of paper. An experienced investor, Redlitz instantly recognized something in them. He’d spent years evaluating startup founders, and these men had the same look: the restless focus of someone who sees a future they haven’t built yet.

That evening, Redlitz came home with a bold new idea. He wanted to go back. Not just once—he wanted to build an entrepreneurship program inside San Quentin. Beverly Parenti, his wife and business partner, was not immediately on board. Her first reaction was closer to alarm than enthusiasm. A prison? Every week? With no funding, no infrastructure, and no clear endgame? It was, by any reasonable measure, a crazy idea.

The “Crazy Idea” That Sparked A National Movement

It was, in fact, the first of what The Last Mile now fondly refers to as “Chris’s Crazy Ideas”—a phrase that has since become part of the organization’s internal language, shorthand for the kind of audacious, not-entirely-logical leaps that have defined TLM’s trajectory from the beginning. 
 
Despite all hesitation, Beverly also saw first-hand the incredible potential of the men in San Quentin. Together, they turned a wild impulse into a weekly commitment, then a program, and then a movement more than a decade in the making.
 
They called it The Last Mile. It started without a strategic plan, a board, a line item budget. Most of the participants were serving life sentences. There were no computers, no internet, no projectors. What they had was a whiteboard, a storage closet repurposed as a classroom, and a belief—untested but deeply felt—that the people inside those walls were capable of building something extraordinary.
 
Fifteen years later, entrepreneurship is returning to the facility, now known as San Quentin Rehabilitation Center, in a form that none of them could have imagined in that storage closet. The new program is co-designed by justice-impacted leaders, built to respond to a labor market being reshaped by AI, and delivered inside a purpose-built, technology-enabled classroom. What once fit inside a closet is now poised to reshape the national conversation about what prison education can actually do.

The Original Cohort and the Power of Proof

The first entrepreneurship cohort at San Quentin had almost nothing in the way of resources. But they had something harder to manufacture: drive.

Students worked late into the night on business plans and brand concepts, writing and rewriting pitches until the language was tight enough to hold up in a boardroom. They taught themselves to present with clarity and conviction. The program culminated in a Demo Day, where students stood before a room of business leaders and investors and made their case.

In many ways, that first shaped the DNA of the organization. They proved that entrepreneurship education inside prison should not be considered charity. It was an investment in the future of the entire community.

Redlitz still carries the memory of those early sessions. “These men showed us what was possible,” he said. “They were thoughtful, creative, and committed. Some of those first students are still part of our network today—mentoring others, building businesses, helping shape the future of TLM.”

A Strategic Pivot to Meet a Changing Labor Market

After several successful cohorts, The Last Mile made a critical decision: expand into coding. In true entrepreneurial style, the pivot was a strategic response to what the labor market was demanding.

The numbers told a clear story. In 2013, The U.S. faced a projected shortfall of over one million unfilled computer science jobs by 2020. Fewer than half of American high schools even offered computer science courses. In fast-growing regions like Silicon Valley, companies were desperate for skilled developers. For The Last Mile, coding offered something entrepreneurship alone couldn’t: a scalable, market-driven pathway into high-wage, high-demand careers.

After countless hurdles associated with building a computer lab in prison, the coding curriculum launched and grew rapidly, expanding across multiple states and reaching thousands of students. The outcomes were striking: a 75% employment rate among returned citizens and a recidivism rate below 5%. But even as coding took center stage, entrepreneurship never really left. It lived in the culture—in how students approached problems, pitched ideas, and carried themselves.

How The Dawn Of AI Changed Everything

Toward the end of 2024, the ground shifted again.

Kevin McCracken, Executive Director of The Last Mile, had been watching the labor market with growing unease. “The coding programs filled a clear gap,” he said. “But we also started seeing how fast the job market was changing—especially with AI. We realized that many of the roles we were preparing people for might not exist in five years.”

Advances in AI have begun to automate many entry-level coding tasks. Large language models are now writing production-level code, quietly eroding demand for junior engineers—especially those without industry networks or four-year degrees. For people coming out of prison, already fighting upstream against stigma and gaps in their resumes, the window was narrowing.

The Last Mile recognized that technical skills alone were no longer enough. The next generation of programming needed to equip students with something AI can’t replicate: the ability to think on their feet, communicate persuasively, solve problems creatively, and build something from nothing.

In other words, it needed entrepreneurship.

For some, entrepreneurship is a practical response to reality. Gary Green, a TLM Alumnus and Senior Manager of Academic Success, helped build the new curriculum; “Many of us see entrepreneurship as an elective dream,” he explains. “But for some incarcerated students, it’s a necessity rather than an elective choice.” Even as fair chance hiring initiatives expand, significant barriers remain—especially for those with violent records. “When the traditional job market presents a wall,” Gary says, “entrepreneurship provides the tools to build your own door.”

Reintroducing Entrepreneurship for a New Era

The Last Mile’s expanded curriculum now includes “Pathways” covering Digital Literacy, Project Management, Sales, Entrepreneurship, and more. The new Entrepreneurship Pathway is grounded in the same principles that shaped the original program, but the content has evolved to meet a world that looks very different from 2010.

For Redlitz, the return to entrepreneurship is a strategic adjustment that goes beyond teaching a specific skillset. “Entrepreneurship is not just about creating a business. It’s a mindset,” He reflected to us in a recent interview. “It’s a way you approach things. It’s about questioning your surroundings and gaining confidence to change them.” 

Inside prison, that mindset shift can be transformative. It challenges people to question assumptions they’ve held for years, reframe limitations as design constraints, and begin to imagine alternative outcomes for their lives. Redlitz describes entrepreneurship as “trying and failing and trying again”—a process that builds resilience rather than dependence on certainty.

He also sees it as a hedge against a future that no one can fully predict. “You’re never going to be better than the AI in terms of its ability to code,” Redlitz said. “But if you can be agile from a systems perspective, then you can constantly adapt. That’s what entrepreneurship teaches.”

Ryan Modjeski, Chief Operating Officer of The Last Mile, led the curriculum design for the new Entrepreneurship Pathway. For Modjeski, the blend of hard and soft skills is what makes it work.

What the New Entrepreneurship Pathway Covers

The Entrepreneurship Pathway is designed to develop business fluency, digital literacy, and internal leadership in tandem. Students learn to think strategically, communicate with clarity, manage risk, and build a professional identity rooted in ownership and resilience—all through the framework of starting a business from scratch.

The curriculum blends rigorous business frameworks with deep personal development. Students work through structured models like the Business Model Canvas while also building emotional intelligence, negotiation skills, and a long-term vision for their lives after release. The result is a pathway that strengthens both economic opportunity and personal agency.

The core pillars include:

Entrepreneurial Strategy & Business Design — Students learn to map value propositions, analyze product-market fit, study competitive landscapes, and craft pitches that hold up under scrutiny.

Emotional Intelligence & Resilience — The curriculum addresses the psychological dimensions of professional growth: distinguishing shame from guilt, reframing setbacks, managing fear in high-pressure settings, and building a purpose-driven mindset.

Self-Leadership & Personal Vision — Students define their own vision of success, create a “character blueprint,” set goals with built-in risk mitigation, and take ownership of their professional growth.

Advanced Professional Skills & Collaboration — From brand storytelling to negotiation to active empathy in team settings, this pillar develops the communication skills that separate capable professionals from truly effective ones.

The pathway culminates in a Shark Tank–inspired final pitch presentation. Students develop and present their ventures to a panel, simulating the experience of pitching real investors. For Green, this element made the program feel tangible. “The shark tank style pitch makes the dream of becoming an entrepreneur real,” he says. “It reflects what students see entrepreneurs outside of incarceration doing. That makes it powerful.”

Co-Designed With Justice-Impacted Leaders

One of the most meaningful evolutions of the new program is who helped build it.

This time, the curriculum was not designed solely by experienced entrepreneurs looking in. It was co-created by people who once sat in those same classroom seats—people who understand the carceral environment from the inside out.

Sierra Robinson, a formerly incarcerated TLM alumna who helped design the new Entrepreneurship Pathway, describes entrepreneurship as “a powerful way of thinking that helps students solve problems and bring new ideas to life, regardless of your past.” For her, the relevance is deeply personal. “It empowers you to be self-sufficient by teaching you to rely on your own abilities and unique story as an asset.”

Green describes the design process as “student-first.” Having sat in those same seats, the team understood the constraints of a correctional environment from the inside. “We didn’t want to build a course that worked around the limitations of prison,” he explains. “We built one that delivers a world-class educational experience despite them.”

That shift—from waiting for opportunity to creating it—is central to the curriculum’s design. Robinson believes entrepreneurship restores something incarceration often erodes: agency. “Rather than waiting for opportunities to come to you, this mindset gives you the confidence to take control of your own future and create a career on your own terms.”

A Full Circle Moment – With An Essential Difference

For Robinson, helping build the course was a full-circle moment. “Transitioning from sitting in those classroom seats and feeling the power of education to developing content for our future students was a profound, full-circle moment,” she said. She brought her lived knowledge of prison classrooms into the design process to ensure the language and structure would be “accessible, authentic, and purposeful for students.”

The team itself was largely composed of returned citizens. That collective experience shaped the curriculum in ways no outside consultant could replicate. “Because we were able to bring our collective lived experiences to the table, we could build a well-rounded, universally understandable curriculum that addresses the internal challenges that often hold you captive long after physical confinement has ended,” Robinson explained.

The result is a course that does more than teach business mechanics. It aims to help students reframe setbacks as “setups for comebacks,” develop emotional intelligence, and transform personal pain into purpose. In Robinson’s words, entrepreneurship education in prison is different because “it empowers students to be the architect of their own freedom.”

That difference matters.

A New San Quentin Classroom Built for Innovation

If the original classroom was a statement about resourcefulness—a whiteboard in a storage closet, proof that great teaching can happen anywhere—the new classroom at San Quentin is a statement about belief.

“This new space sends a different message,” Kevin McCracken reflected after a recent site visit. “It says: this work matters. These students matter.”

The space is purpose-built and technology-enabled, designed for modern instruction and creative collaboration. It features writable walls, mobile desks for group work, and modular zones for small-group learning—all designed to build communication skills and project-based thinking. For the first time in San Quentin’s history, students in this program can work on networked computers inside the facility, using curated educational platforms in a secure, controlled environment.

Every tool in the space had to be approved by the California Department of Corrections and Rehabilitation, then configured to operate without standard internet access. Despite those constraints, students can engage with tools for research, branding, design, and presentation-building—resources that are virtually unheard of in traditional prison classrooms.

For Redlitz, walking into the new space is an emotional experience. He remembers the closet. He remembers the whiteboard. He remembers the faces of the men who showed up anyway.

“This space is inspirational,” He told us. “It lets us build and nurture communities inside. When you invest in the environment, you invest in belief.” 

The classroom sets a new standard for what is possible in correctional education—not just at San Quentin, but nationwide. And if The Last Mile’s track record is any indication, it’s only the beginning. More of Chris’s Crazy Ideas are in the pipeline—innovations in how education is built and delivered inside correctional facilities that have the potential to reshape the landscape entirely.

Entrepreneurship and Long-Term Impact

Bringing entrepreneurship back to prison isn’t a nostalgic gesture. It’s a recognition that the most durable skills are the ones that help people navigate uncertainty—not just the labor market of today, but whatever comes next.

For Green, the impact goes beyond business mechanics.

“Entrepreneurship is a journey toward reclaiming power over your time, your income, and your life,” he says. “It’s about taking ownership of your earning potential and your identity.”

The program equips students to contribute meaningfully, whether through launching a business, excelling in employment, or leading in their communities. It complements technical training with human-centered tools that remain relevant even as industries shift beneath people’s feet.

Unlike traditional job training programs that prepare students to depend on someone else’s approval, entrepreneurship reframes success entirely. “Most job-focused training prepares a student to be reliant on someone else’s ‘yes’ to gain employment,” Green says. “Entrepreneurship flips that script. It teaches students that they can take ownership of their success. It’s the difference between waiting for an opportunity and creating one.”

The Next Era Of Rehabilitation, 15 years In The Making

The United States incarcerates more people than any nation on earth. Moral implication aside, the size of the American prison population shows that the system itself requires an innovative redesign. No other country faces mass incarceration at this scale, which means no other country is going to solve it for us. The solutions have to come from here—from organizations willing to rethink what’s possible inside facilities that were never designed for possibility.

The Last Mile has spent fifteen years proving that the people society has written off are capable of extraordinary things. The entrepreneurship program’s return to San Quentin is one chapter of that proof. But the story is far from finished. What comes next—how education is delivered, how technology is deployed, how the system itself begins to bend—may be the most important chapter yet.

As The Last Mile looks ahead, this full-circle moment carries the weight of everything that came before it—every late-night business plan, every Demo Day pitch, every student who walked out of those gates and built a life worth living. The program has evolved. The classrooms have changed. The technology would be unrecognizable to the men who gathered around that whiteboard in 2010.

But the mission hasn’t moved an inch: unlock human potential and break the cycle of incarceration.

Written By Robert Roche and Kevin McCracken