Changing Lives.
Before and After the System.
Meet Chris Wolfe—speaker, entrepreneur, & advisor
Stopping Sentences Before They Start
Speaker
Chris Wolfe is a compelling and compassionate communicator who brings lived experience and deep insight to every stage he steps on. His talks help parents, educators, and young people understand the critical choices that lead to incarceration—and how those paths can be interrupted before it's too late. With a gift for storytelling and a message grounded in both empathy and accountability, Chris challenges audiences to think differently about risk, resilience, and redemption. Drawing from hundreds of in-depth conversations with men who’ve spent decades behind bars, he delivers powerful, perspective-shifting talks that illuminate both the warning signs and the way forward.
Advisor
As a trusted advisor and board member of the RBS Corrections Transition Program, Chris is passionate about preventing incarceration before it begins, offering insight, ideation, and honest feedback drawn from lived experience. As a former spokesman for the National Marijuana Initiative, Chris provided critical education on substance use and decision-making. Whether advising on prevention or reentry, he brings clarity, empathy, and hard-won experience to the table.
Entrepreneur
With four decades of experience as a business owner and professional speaking instructor, Chris brings an entrepreneurial spirit to his prevention and reentry work. He’s built programs that not only prepare incarcerated men for life after prison, but also help prevent young people from ending up there in the first place. In 2007, he founded the Voices of Time Gavel Club inside Everglades Correctional Institution—an initiative that equips life-sentenced men with communication and critical thinking skills. Since then, his program has helped nearly 600 men transition successfully, with a recidivism rate of less than 1%. Chris believes that when you invest in education, early and often, transformation becomes possible.
TESTIMONIAL
“Chris’s insights into juvenile intervention offer both a sobering reality and a hopeful path forward.”
Paula Hesch
What led Chris to this work
I've always been drawn to stories about prison, ever since I was a kid watching movies like The Great Escape, Cool Hand Luke, Midnight Express, and The Shawshank Redemption. There was something about that world that fascinated me, maybe because it’s a part of society most people ignore or don’t understand. As someone once said to me, “It’s a segment of society very few people really know about or care about.” But I do. I always have.
What began as curiosity turned into a calling when I learned just how many people are sentenced to life in prison as teenagers. These are kids—many of them never given a real chance—who grow up behind bars. I realized how little we do to educate parents, teachers, and young people about the consequences of breaking the law. That’s why I’ve dedicated myself to this work. Because they matter. And their stories deserve to be heard.
Guiding Young People Away from Prison and Toward Possibility
Signature Keynotes
My mission
To prevent incarceration by educating and empowering youth, families, and communities with the knowledge, tools, and real-life stories that illuminate the path toward better choices. Chris Wolfe uses storytelling and teaching to foster understanding, encourage education, and support transformation, while also helping those who have served long prison sentences successfully reintegrate into society with purpose and dignity.
My promise
A future where incarceration is the exception, not the expectation. Chris believes in the power of prevention, the possibility of change, and the importance of second chances. Through honest conversation, empathy-driven education, and decades of real-world experience, he helps communities see the human being beyond the headline—and imagine a society where every person has the opportunity to grow, contribute, and be seen for who they are today.
Professional biography
Board of Directors, RBS Corrections Transition Program
Chris Wolfe is a nationally recognized speaker, entrepreneur, and advisor passionate about preventing incarceration and guiding meaningful transformation, both before and after a prison sentence. With a career spanning more than 40 years in entrepreneurship and communication, Chris brings deep experience, clarity, and compassion to the stage and beyond.
A powerful voice in prevention, Chris speaks with students, parents, and professional associations to illuminate the early warning signs that can lead young people down a destructive path. Through candid storytelling, data-informed insight, and hard-won wisdom, he inspires audiences to intervene earlier and more effectively—empowering youth before they enter the justice system. His work on the podcast, Men Going Home, shares real-life stories of incarceration to foster empathy, reflection, and change.
At the same time, Chris has spent nearly two decades helping life-sentenced men prepare for parole and successful reentry into society. In 2007, he founded The Voices of Time Gavel Club at Everglades Correctional Institution, an initiative that equips men with critical communication and leadership skills. To date, the program has supported the successful reentry of nearly 600 men, with a recidivism rate of under 1 percent—a remarkable achievement in a state where the average exceeds 20 percent.
Chris has served as a spokesperson for the National Marijuana Initiative’s speakers’ bureau, where he educated audiences on the risks and consequences of substance use. He has conducted hundreds of interviews with incarcerated men—many of whom spent 25 to 50 years behind bars for first- or second-degree murder and armed robbery, including time on death row. He also sits on the Board of Directors for the RBS Corrections Transition Program, bringing lived experience and insight to support second chances.
A longtime member of Toastmasters International, Chris has served multiple terms as President of the Miracle Mile Toastmasters Club in Coral Gables, FL, and has competed in numerous public speaking competitions. Whether speaking to teens, teachers, or professional associations, he bridges incarceration and intervention with a message of hope, accountability, and the transformative power of human connection and second chances.
