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.

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.

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.

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.