Anthony Milbourne traveled all the way from Australia to sit down with Ian Bick and share his journey into becoming a correctional officer inside an Australian youth prison. In this episode, Anthony breaks down how his life experiences led him to the job, what daily life was really like inside the facility, and the key differences between the Australian and American prison systems — from food, routine, and commissary to discipline and inmate culture. He also opens up about the violent attack he suffered at the hands of inmates, an incident that ultimately pushed him to walk away from the career.

Troy Ave sits down with Ian Bick for an honest conversation about his upbringing, the path that led him into the criminal justice system, and what it took to survive time at Rikers Island. In this episode, Troy Ave breaks down his early life, the court case that changed everything, the realities of being locked up inside Rikers, and how incarceration reshaped his mindset both personally and professionally. He speaks honestly about accountability, survival, and navigating life after the system while continuing his journey in music.

Sarah Wayne Callies sits down to talk about her childhood, her path into acting, and what led to her being cast as Dr. Sara Tancredi on Prison Break. She opens up about the sudden fame that came with the show, how she prepared for the role by visiting real prisons, and how filming Prison Break permanently changed her perspective on incarceration and the criminal justice system. Sarah also shares behind-the-scenes stories from set, the emotional weight of playing a character inside prison walls, and how that experience later influenced her work, including being cast on The Walking Dead.

Amanda Tarver opens up about one of the most shocking chapters of her life, discovering she was pregnant just weeks after self-surrendering to federal prison, navigating pregnancy and childbirth behind bars, and the emotional reality of giving birth while incarcerated. In this conversation with Ian Bick, Amanda breaks down how her decisions led to federal prison time, the trauma and resilience of motherhood inside the prison system, and how that experience inspired her and her husband to start 300 Letters, a nonprofit supporting families impacted by incarceration and helping break the cycle of trauma.

Legend Tarver went from graduating with a degree to serving time in federal prison, learning the hard way how choices, survival, and consequence intersect in the criminal justice system. Two weeks into his sentence, he found out his then-girlfriend, Amanda, was pregnant, and the couple endured separation, hardship, and the challenges of incarceration while growing their family. Drawing strength from the more than 300 handwritten letters they exchanged behind bars, Legend and Amanda turned their experience into purpose by co-founding 300 Letters, a nonprofit dedicated to treating incarceration as a family affair and helping justice-impacted families heal, stay connected, and rebuild after prison. In this episode, Legend opens up about how he ended up in prison, how that time shaped his life and fatherhood, and how he’s working now to change the narrative for others who’ve faced similar struggles.