The podcast episodes discuss the personal experiences of individuals who have served time in prison, providing a window into the harsh realities of incarceration.

In #2107 - Billy Walters, legendary sports bettor Billy Walters shares his firsthand account of serving a 31-month prison sentence, describing the poor conditions and lack of medical care at the facility.

Similarly, in Steve Madden Loves Quaaludes, Hates Adderall, & Is Addicted To Nose Spray, shoe designer Steve Madden discusses his time in federal prison, challenging the misconception of it being a 'country club' and highlighting the difficult realities of life behind bars.

Lastly, in 132: Sam the Vendor, former darknet market vendor Sam Bent shares his experiences of serving time in prison for his illicit activities, including his compassionate release and subsequent efforts to help others navigate the legal system.