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.

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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.

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Dillan Judkins grew up in Utah after being put up for adoption at birth by his mother, who was struggling with addiction, and raised by a loving Mormon family — but rebellion, alcohol, and trouble started early. In this episode, Dillan shares how a sexual assault charge stemming from a one-night stand at a party when he was 18 changed his life forever, leading to months in county jail awaiting trial, a probation deal, repeated violations, and ultimately spending nearly 15 years inside the Utah prison system. He explains how he survived prison with a stigmatizing charge, his side of the story, the realities of navigating the system, and the long-term impact incarceration has had on his life, identity, and future.

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Brian Watson spent over 20 years as a special agent in the IRS Criminal Investigation Division. In this episode, he explains how he got into the IRS, what the job is really like, and how criminal tax evasion cases are built from start to finish. Brian breaks down common myths about the IRS, how payroll tax cases work, what restitution actually means for defendants, and how investigations move from audits to criminal charges. This conversation offers a rare inside look at IRS criminal enforcement from someone who spent decades inside the system.

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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.

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LUCY: Go to HTTP://LUCY.CO/IANBICK and use promo code IANBICK to get 20% off your first order.

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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.

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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.

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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.

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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.

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LUCY: Go to HTTP://LUCY.CO/IANBICK and use promo code IANBICK to get 20% off your first order.

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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.

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LUCY: Go to HTTP://LUCY.CO/IANBICK and use promo code IANBICK to get 20% off your first order.

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