Nightmare Success
Nightmare Success is a podcast hosted by Brent Cassity that gives voice to people whose lives were altered by incarceration—and whose stories became remarkable comebacks. Cassity, a former CEO who served a federal sentence himself, brings lived experience and empathy to the conversations. Each week he meets with someone who has walked through the worst of the criminal-justice system and emerged with purpose, resilience and action.[1][2]
History
The podcast launched in 2021, at a time when stories of justice-involved individuals were gaining broader attention. From its inception, it focused on bringing depth and authenticity to the conversation: life before prison, life inside, and life after release. By late 2025 the show had produced over 200 episodes and entered its fifth season.[3] Over those years it grew from a niche-justice audience into one of the most trusted platforms for understanding incarceration, redemption and second chances.
Popular episodes
Host
Host: Brent Cassity Brent Cassity is a former national-company CEO, author and podcast host. He built his career leading a family-owned business in the funeral, cemetery and preneed-insurance sector that expanded across more than 20 states.[4] His business achievements earned national recognition in publications such as The Wall Street Journal and TIME magazine; an HBO documentary titled The Young and the Dead featured the company’s story.[5] Then Cassity faced a federal prosecution and served a five-year federal sentence.[6]
References
- ↑ Apple Podcasts. “Nightmare Success In and Out – Podcast (Brent Cassity).” https://podcasts.apple.com/us/podcast/nightmare-success-in-and-out/id1588287560
- ↑ NightmareSuccess.com. “Nightmare Success – The Podcast.” https://nightmaresuccess.com/
- ↑ Rephonic. “Nightmare Success In and Out – Audience & Stats.” https://rephonic.com/podcasts/nightmare-success-in-and-out
- ↑ Brent Cassity. “Meet Brent.” https://brentcassity.com/
- ↑ Mark Graban. “CEO Brent Cassity Trusted His Dad and Ended Up in Prison for Fraud and Conspiracy.” December 8, 2021. https://www.markgraban.com/ceo-brent-cassity-trusted-his-dad-and-ended-up-in-prison-for-fraud-and-conspiracy/
- ↑ U.S. Attorney’s Office, Eastern District of Missouri. “Six Defendants Sentenced To Total Of 36 Years In Prison In National Prearranged Services Case.” November 14, 2013. https://www.justice.gov/usao-edmo/pr/six-defendants-sentenced-total-36-years-prison-national-prearranged-services-case