How To End Prison Recidivism

Chris Redlitz
Co Founder and Executive Director of The Last Mile
1hr 30min
September 21, 2023
About the Show

“What I saw in those men was what I saw in many of the founders that pitched me. It was something in their eyes and the questions that they asked me. I had several guys hand me business plans that they wrote with a prison pencil.”

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Chris Redlitz is the Co Founder and Executive Director of The Last Mile, leading a national movement across our country to provide in-prison technology education and post-incarceration mentorship to justice-involved people across the United States. Chris was previously the exiting founder of Second Sole, AdAuction.Com, and Feedster, and he founded Kicklabs, a fund and incubator that has helped launch and grow 38 tech companies to massive exits. 

Throughout the interview, Chris shares personal stories and anecdotes that shed light on the realities of entrepreneurship. From the pain of a failed IPO to the importance of having a supportive partner, Chris' stories captivate and inspire listeners. Chris' experience and wisdom offer valuable lessons and insights for navigating the challenges and opportunities that come with building a business.


Key Moments

A Journey Of Rehabilitation And Redemption

The setting sun threw a soft glow over San Quentin Prison, its historic walls holding thousands of lives from the outside world. Chris Redlitz crossed the empty yard towards the towering building, wondering what he was getting himself into. He had agreed to a talk to some of the inmates of San Quentin who were interested in entrepreneurship, but Chris was skeptical that he or his 30-minute presentation would be well received in such a foreboding place. He reflected on his past accomplishments and wondered how useful his experience could be for a group of incarcerated men, some of them for life sentences.

When it came to talking about entrepreneurship, Chris certainly had the experience to back it up. After spending his young adult years on adventures around the world, including a 3-person sailing trip to Hawaii with no digital navigation equipment, Chris followed his passion for ultra-running and founded Second Sole, a retail chain in California for high-level running equipment. Chris’ leadership in that space caught the attention of the rapidly growing sportswear giant Reebok, and Chris's meteoric rise in Reebok and his instrumental role in its massive IPO was the first of many profound successes in his life. Sensing the impending dot-com boom, Chris ventured into the digital realm at the perfect moment, leading to multiple successful acquisitions and many devastating failures.  He then transitioned into the role of venture capitalist, co-founding KickLabs, one of the country's top technology accelerators, and later establishing Transmedia Capital. His keen eye for innovation and empathetic touch made him a pivotal figure in the venture capital landscape, providing funding and invaluable advice to a multitude of startups in the tech sector that achieved significant growth and dozens of substantial exits. His reputation in the VC world is not just as an investor, but as a mentor and visionary who could foresee tech trends and guide nascent businesses to monumental success.

Fostering Entrepreneurial Thought In Prison

To say he was surprised by his experience that night in San Quentin would be an understatement. What was meant to be a brief presentation transformed into a riveting three-hour discourse with an unexpected audience: A group of inmates with entrepreneurial dreams, and a burning ambition to change the course of their lives for the better. Chris found himself meeting with a group of inmates who displayed an astonishing grasp of business concepts, a hunger for knowledge, and a genuine desire to reach their full potential. These were men who, despite their past mistakes, showed a palpable eagerness to become successful entrepreneurs.

Despite their dreams, these men faced an uphill battle against an unforgiving environment. The United States has one of the highest incarceration rates globally; with over 2.3 million individuals behind bars, the country's prison system has been under scrutiny for its approach to rehabilitation. The statistics on recidivism, or the tendency of a convicted criminal to re-offend, are telling. Within three years of release, about 67.8% of released prisoners are rearrested, and within five years, that number climbs to 76.6%.

Such staggering figures point to a fundamental flaw in the prison system. Rather than focusing on rehabilitation and reintegrating inmates into society, the system usually perpetuates a cycle of re-incarceration.

Chris Redlitz's encounter with the entrepreneurially-minded inmates at San Quentin was a pivotal moment in his life, along with the lives of every person he would work with moving forward. It laid the foundation for The Last Mile, leading a national movement across our country to provide in-prison technology education and post-incarceration mentorship to justice-involved people across the United States. In collaboration with his co-founder and partner Beverly Parenti, Chris and the Last Mile team have transformed the lives of countless individuals. By equipping them with skills in coding, web design, entrepreneurship, and other high-value fields, The Last Mile ensures that these individuals have a fighting chance at securing meaningful employment upon release.

Changing The Tide Of Prison Recidivism

These programs have shown staggering results in their participants, with many previously incarcerated people entering into six figure positions at leading tech companies in the Silicon Valley. The impact doesn’t end there - Chris and Beverly have expanded the programming to help the families and especially the children of incarcerated people to help build the skills and confidence of the next generation, a group of young people who are often victims to the pressures and traumas of having their parents in the prison system. The Last Mile truly lives up to its name by making sure no stone is left unturned on the road to rebuilding lives, families, and communities. 

The success of TLM isn't just in its training program. The company itself stands as a beacon of hope, with a significant portion of its staff comprising previously incarcerated individuals. These are individuals who have walked the path, faced the challenges, and emerged triumphant. Their presence serves as a constant reminder of the transformative power of rehabilitation and the potential that lies within every individual.

In a society that often writes off incarcerated individuals, Chris Redlitz and The Last Mile stand as a testament to the power of redemption. Through tech training, mentorship, and unwavering belief in the potential of these individuals, these visionary people are not just reducing recidivism rates; they are transforming lives. It's a movement that challenges the existing paradigm, urging society to look beyond the prison walls and see the potential that lies within.

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