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.

Cory Simek grew up in Texas surrounded by crime and addiction, with both of his parents involved in drug dealing and his father eventually sentenced to prison. Following in his family’s footsteps, Cory found himself in and out of Texas jails before ultimately receiving a state prison sentence. In this episode, Cory shares what it was really like surviving Texas state jails and prisons, including running with an independent prison group, navigating constant violence, and learning the unspoken rules of life behind bars. He opens up about how his upbringing shaped his choices, the realities of incarceration in Texas, and the moments that forced him to confront where his life was headed.

Jim Cole, a retired Supervisory Special Agent with Homeland Security Investigations (HSI) and global expert on child exploitation and victim identification, sits down to reveal the untold truth about fighting child predators and digital crime. With nearly 35 years in law enforcement, Jim led major initiatives including founding the HSI Victim Identification Program, co-founding Project VIC to help identify and rescue thousands of children worldwide, and serving as Chair of the INTERPOL Specialists Group on Crimes Against Children. He now serves as Chief of Law Enforcement Enterprise & Technology at Operation Light Shine and partners with law enforcement, technology providers, and nonprofits to innovate how child exploitation investigations are handled. In this heart-breaking conversation with Ian Bick, Jim shares inside stories from real cases, the mental and emotional toll of this work, and why putting victims first changes everything in the fight against online predators.