Joseph De Gregorio was raised in a good family and built a successful career on Wall Street, but the 2008 market crash derailed everything. After losing his footing, he started his own business, which eventually turned into a fraud scheme—a decision he ultimately took responsibility for by coming clean and turning himself in to authorities. At the same time, Joseph was battling a severe alcohol addiction, drinking himself to the point of needing a liver transplant. He was later sentenced to federal prison, where he faced harsh conditions and medical challenges while serving time in a federal medical center prison. After his release, Joseph reinvented his life, dedicating himself to helping others navigate the justice system through prison consulting and sentence mitigation work, turning his darkest chapter into a mission to help people avoid the same mistakes.

Ernie Leon shares a story of survival, violence, and redemption. Growing up in Arizona, Ernie fell into addiction and gang life at a young age, which led to an armed robbery conviction and time in the Arizona prison system. After getting into trouble behind the walls, he was sent to maximum-security prison, where survival became a daily battle. Following his release, tragedy struck when Ernie witnessed his brother get shot and killed, and Ernie himself was shot and paralyzed. Despite everything, he was later sent back to Arizona max prison on another armed robbery case. In this conversation, Ernie breaks down the realities of Arizona maximum-security prisons, the consequences of street life, and what it takes to keep going after losing everything.

Paul Collette spent years working inside the criminal justice system as a New York probation officer before leaving to become a federal probation officer. In this episode, Paul pulls back the curtain on what probation really looks like, sharing real stories from the job while breaking down the biggest myths and truths the public gets wrong. He talks about supervising violent criminals and sex offenders, handling high-risk situations, and the daily pressure of balancing public safety with rehabilitation. From the differences between state and federal probation to the realities of working with dangerous individuals, this conversation offers an unfiltered, insider look at life behind the badge and what it truly means to work inside the probation system.

Max B sits down with Ian Bick for a raw, open & honest conversation about his life, music, and surviving more than 15 years behind bars. He opens up about growing up in Harlem, his first prison sentence at Rikers Island and in New York State prison, and how he initially got into music and rose to fame. Max B then breaks down his second arrest, being sentenced to 75 years in prison, and what it took to survive New Jersey State Prison while continuing to put out music from behind the walls. He also shares how his sentence was eventually reduced, the mindset that kept him going, and what it’s been like finally getting out of prison and moving forward with his life.

Matt Crosby shares how getting caught selling drugs led him from a Rhode Island county jail to serving time in a state prison. In this episode, Matt breaks down the choices that put him on that path, what county jail was really like compared to state prison, and how incarceration forced him to confront the reality of his decisions. He speaks honestly about the mindset that comes with drug dealing, the shock of incarceration, and the long-lasting impact prison has on your life even after release.