Steven Johnson grew up in Connecticut surrounded by instability and a rough childhood that pushed him toward the streets at a young age. As a teenager, he joined the Latin Kings and quickly rose through the ranks, eventually becoming a chapter president before landing in Connecticut state prison. While serving time in the late 1990s and early 2000s, Steven made a decision that could have cost him his life — walking away from the gang while still incarcerated. In this episode, he shares what prison was really like during that era, how he survived the consequences of leaving the Kings behind bars, and how that choice completely changed the course of his life. After his release, Steven never looked back, building a new path rooted in discipline, accountability, and staying out of the system for good.

Michael Bishop grew up surrounded by emotional trauma, bullying, homelessness, and instability, moving in and out of the foster care system while dealing with serious issues at home. Fighting became a way to survive, and that anger eventually led to him being locked inside Massachusetts juvenile detention centers for nearly two years. In this episode, Michael shares a firsthand account of life inside youth detention, including physical abuse by guards and the long-term impact of being punished instead of protected. This conversation exposes the harsh realities of the juvenile justice system and how a broken upbringing and systemic failures shaped the course of his life.

Matt Frey spent seven years working as a therapist inside Rikers Island from 2011 to 2018, a job he never imagined taking growing up in the suburbs of New York. In this episode, Matt gives a rare inside look at day-to-day life at Rikers from the inmate perspective, breaking down what really happens in both General Population and Mental Observation housing. He shares firsthand experiences with extreme violence, inmate suicides, unprovoked attacks on staff, and the psychological toll of working inside one of America’s most notorious jail systems. Matt also explains how inmates sometimes manipulate mental health services for protection or legal advantage, what it’s like hearing confessions protected by confidentiality, and the surreal reality of assessing people just hours after seeing their alleged crimes on the news. Now running his own psychotherapy practice after leaving Rikers, Matt reflects on boundaries, trauma, and how working inside the jail changed him forever.

Dylan Syer speaks publicly for the first time about the high-profile accusations that upended his life, including allegations of fraud, identity theft, and grand larceny stemming from his work as a celebrity personal shopper. Prosecutors claimed Dylan used access to clients’ finances to make unauthorized luxury purchases, accusations he firmly denies. In this episode, Dylan explains what he says really happened, how the charges caused his business to collapse overnight, and what it was like being sent to Rikers Island while fighting to clear his name. He also opens up about the emotional toll of the case, navigating the criminal justice system, and ultimately being sentenced to one year of weekends at Rikers — a punishment that kept him trapped between freedom and incarceration.

Andrew Gautreau grew up in a good family in Louisiana, but addiction took hold in his teenage years and quickly sent his life off the rails. After finishing trade school, he began getting arrested for drug offenses — yet somehow still landed a job as a prison guard, training for a month at Angola, one of the most notorious prisons in America. His time on the job lasted just six months before he quit right before being fired, all while being arrested twice for drug charges outside the prison. As his addiction spiraled further, Andrew ended up cycling through local jails and a correctional work facility, where he spent nearly two years behind bars. In this episode, he opens up about addiction, hypocrisy inside the justice system, life on both sides of the bars, and how he ultimately turned everything around and got sober.