Jason Abreu grew up in a good family, on track to become a lawyer, until the recession blew up his plans and pushed him into the New York City nightlife scene. What started as legit nightclub promoting slowly turned into moving drugs through NYC clubs, big money, fast nights, and a double life he thought he had under control. Then undercover cops took him down, and Jason was sent to New York state prison. He got out, went right back to the game, and got caught again, earning a second trip upstate. In this episode, Jason sits down with me and breaks down exactly how it happened: the first bad decision, how the nightclub world really works, the rush of easy money, the takedown, and what New York state prison is actually like on the inside, from daily politics to survival.

Anna Delvey sits down with Ian Bick and finally tells the part of her story the world hasn’t heard, not the fake heiress headlines, but the arrest, LA County jail, surviving Rikers Island, doing time in New York state prison, and ending up in an ICE detention center, breaking down the everyday survival, politics, fear, and pressure of prison life that no Netflix series ever showed.

Dr. Joseph Williams was raised in Brooklyn by his mother and grandmother, but the allure of the streets quickly led him into fighting, selling crack, and a 4-year bid in New Jersey. After returning home and falling back into the lifestyle, Joe committed a brazen movie theater robbery that resulted in a stiff 11-year sentence in New York State prison. In this episode, we dive into how Joe survived the New York prison system, earned his college degree behind bars, and turned his life around to become a Licensed Clinical Social Worker dedicated to breaking the cycle of recidivism.

Jesse Smithers was just a teenager when a street fight turned fatal, forcing him to accept a 10-year plea deal in the Minnesota prison system. In this interview, Jesse breaks down how he survived a decade behind bars only to face a new battle upon release: a system that wouldn't hire him. Pushed back into selling drugs to survive, Jesse reveals how a miraculous case dismissal became the final wake-up call he needed to leave the life of crime behind forever.

David Bell sits down with Ian Bick to break down his unconventional path through the criminal justice system — from going to law school for tax law and working at a major firm to walking away and joining the Missouri Public Defender. In this episode, David explains why he chose public defense, what it’s really like defending society’s “worst of the worst,” and how that experience reshaped his view of justice. He dives deep into sentencing guidelines, the use of “ghost dope” to inflate sentences, systemic changes in criminal law, and the real differences between public defenders and paid attorneys. Now in private criminal defense practice in Kansas City, David offers an honest, inside look at how cases are charged, sentenced, and defended — and what most people don’t understand about how the system actually works.