In this episode, we sit down with Reggie Chatman from The Fortune Society, a leading New York–based nonprofit dedicated to supporting successful reentry and advocating for alternatives to incarceration. Reggie shares his journey into this transformative work and opens up about the barriers that formerly incarcerated people face when trying to rebuild their lives through employment and education.

We explore the systemic gaps that leave people returning home without job training, credentials, or fair opportunities—and how those failures often lead to cycles of recidivism. Reggie discusses how The Fortune Society steps in to fill those gaps, offering workforce development, educational programs, and emotional support to empower individuals long after release.

Together, we unpack the myths surrounding reentry, the policies that make it harder for people with records to move forward, and what real reform could look like if we reimagined education and employment systems built on opportunity, not punishment.

Whether you’re a policymaker, employer, educator, or student, this conversation challenges you to think differently about justice, dignity, and the role we all play in creating pathways to true second chances.