Travis Richey was a successful hedge fund owner with a background in finance — until a paperwork mistake landed him in an Arizona state prison. Raised in Boston with family ties to organized crime, Travis built a career on Wall Street before a technicality changed his life forever. In this gripping episode, Travis opens up about his rise in the finance world, the moment it all came crashing down, and how he’s now using his experience to help others through his nonprofit.

DJ Whitmore spent 30 years inside the walls of federal prisons — not as an inmate, but as an associate warden. From serving in the Gulf War to working his way up through the ranks of the Bureau of Prisons, DJ has seen every side of the justice system. In this powerful interview, he shares what really goes on behind bars, from low-security camps to high-security penitentiaries. If you’ve ever wondered what prison is like from the other side — this episode pulls back the curtain.

Roger Upchurch was a successful homebuilder in Indiana—until the 2008 market crash pushed him into the synthetic marijuana trade. He built a multi-million dollar K2 empire, making over $50,000 a week, until an undercover DEA agent brought it all down. At 69 years old, Roger was sentenced to 4 years in federal prison for drug trafficking and money laundering. In this jaw-dropping episode, he reveals how he went from building homes to building a drug empire—and what it cost him.

Kyle Farace grew up with a normal life—until he found out his dad was secretly growing and selling weed. What started as a curiosity turned into a full-blown operation, with Kyle eventually joining forces with his father. But everything changed when he got set up by a confidential informant and an undercover ATF agent, leading to drug and gun charges and a 3-year federal prison sentence. Kyle believes his own father may have had a hand in the setup. In this raw interview, he shares how prison changed him, the hustles that kept him going inside, and the struggle to rebuild life after getting out.

Smiley B grew up in the Bronx without a father figure and was pulled into gang life at an early age. Recruited into the Bloods, he was in and out of juvie and Rikers Island before catching two federal cases that led to 15 years behind bars. From surviving 11 different federal prisons—6 of them being the most violent U.S. penitentiaries—to becoming a shot caller inside, Smiley B lived through it all. In this raw and unfiltered interview, he shares the brutal war stories, the codes of prison politics, and the moment he finally decided to walk away from the life that nearly destroyed him.