
What happens if your worst fear becomes your reality? Brent Cassity was a successful CEO working in a family business that grew to a national company that was recognized by the media of being the pioneers in their industry. Brent had it all and lost it all. He found himself standing at the gates of Leavenworth Prison to serve a 5 year sentence. Brent's podcast explores the stories of inmates who w... more
| Publishes | Weekly | Episodes | 233 | Founded | 5 years ago |
|---|---|---|---|---|---|
| Number of Listeners | Category | Society & Culture | |||

Grammy Award-winning jazz trumpeter Irvin Mayfield Jr. joins Brent Cassity for an unforgettable conversation about success, public failure, federal prison, and rebuilding a meaningful life.
Once celebrated as New Orleans' Cultural Ambassador and one... more
For nearly eighteen years, Damien lived inside a prison cell waiting for the state to execute him.
Most people know the story of the West Memphis Three. They know the headlines, the documentaries, the controversy, and the legal battle that ultimatel... more
Rashmi Airan had it all—an Ivy League education, a successful law career, and a bright future.
Then everything changed.
After becoming entangled in a mortgage fraud scheme during the housing boom, Rashmi faced federal prosecution, prison, and the p... more
Scott Maddox spent decades at the center of Florida politics.
He served as Mayor of Tallahassee, chaired the Florida Democratic Party, and ran statewide campaigns for Attorney General and Governor. He was widely viewed as one of Florida's rising pol... more
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Brent Cassity’s Nightmare Success podcast shows that, although people have made mistakes that have landed them in prison, the moment and the consequence doesn’t define who they are. That in spite of those circumstances people can overcome those moments and find hope, change, possibility, a new life full of meaning and purpose.
Brent creates a space where people impacted by the federal justice system can finally tell their stories. He gives a voice to those who deserve to be heard by shining a light on realities most Americans never see and revealing the human cost of a system that often punishes unfairly. Brent has a rare gift for helping guests open up about their darkest chapters. Nightmare Success Stories is an insightful podcast that truly contributes to the national conversation about reform.
I’ve lived both sides of success—the version the world applauds and the one it turns away from. That’s why Nightmare Success In and Out resonates with me on a different level.
Brent Cassity isn’t interested in surface-level stories. He goes straight to the truth—the mistakes, the consequences, the fallout—and more importantly, what comes after. Being a guest on the show wasn’t just an interview, it was a real conversation about accountability, ownership, and what it actually takes to rebuild a ... more
I was rush indicted on a fraud case so thin, it fell apart immediately once the AUSA was disqualified in a precedent-setting order - there is very little American case law where the optics of a prosecutor were so horrifying the judge had to step in. This roller coaster story didn’t have a home nor media willing to touch it - until Brent Cassity did. Now, what I lack in public vindication, I can at least point to one single place the whole story (or most of it) lives. This has brought unexpected ... more
Brent has created something truly special with Nightmare Success. As a recent guest on the show, I got to experience firsthand what a thoughtful, empathetic, and prepared host he is. He doesn’t just focus on the 'nightmare' of the justice system; he guides the conversation toward the resilience, purpose, and redemption that comes after. He creates a safe space for real vulnerability. Whether you have justice system experience or are just looking for proof that you can rebuild your life after hit... more
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Listeners, social reach, demographics and more for this podcast.
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A compelling look at resilience and reinvention after prison, with guests who recount pre-incarceration success, the experiences inside, and the path forward after release. Episodes often center on legal ordeals, the impact on families, and practical strategies for rebuilding careers, credibility, and purpose. The show stands out for empathetic interviewing, a focus on second chances, and guests who transform hardship into advocacy, coaching, or entrepreneurship, making it useful for listeners seeking inspiration, accountability, and reform-minded perspectives.
Rephonic provides a wide range of podcast stats for Nightmare Success In and Out. We scanned the web and collated all of the information that we could find in our comprehensive podcast database. See how many people listen to Nightmare Success In and Out and access YouTube viewership numbers, download stats, audience demographics, chart rankings, ratings, reviews and more.
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These podcasts share a similar audience with Nightmare Success In and Out:
1. Matthew Cox | Inside True Crime Podcast
2. Locked In with Ian Bick
3. The Joe Rogan Experience
4. Love Trapped
5. This Is Actually Happening
Nightmare Success In and Out launched 5 years ago and published 233 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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Recent guests on Nightmare Success In and Out include:
1. Rasmi Airan
2. Scott Maddox
3. Desmond Meade
4. Kalise White
5. Gordie Ernst
6. Mike Castillero
7. Kelly Givens
8. PJ Jensen
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