
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 | 221 | Founded | 5 years ago |
|---|---|---|---|---|---|
| Number of Listeners | Category | Society & Culture | |||

What happens when your worst fear becomes your reality? On this episode of Nightmare Success In and Out, Brent Cassity sits down with Dr. Ron Elfenbein — a board-certified emergency room physician trained at Johns Hopkins who stepped up when the worl... more
What happens after prison? For most people, that’s where the real struggle begins.
In this episode of Nightmare Success In and Out, Brent Cassity sits down with Doug Feller—an entrepreneur who went from building businesses and living fast… to facing... more
What happens when your worst fear becomes your reality… and you come back determined to rebuild the very system that once held you?
In this powerful episode of Nightmare Success In and Out, Brent Cassity sits down with Kerwin Pittman, a nationally r... more
What happens when your worst fear becomes your reality… and you turn it into art?
On this episode of Nightmare Success In and Out, host Brent Cassity sits down with musician Jason Pears, known artistically as Jason Made, whose life took an unexpecte... 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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Stories focus on lives touched by incarceration, transformation, and reintegration, with conversations that explore life before prison, experiences inside, and the path back home. The show frequently centers on redemption, advocacy, and practical steps to rebuild—often highlighting education, mentorship, entrepreneurship, and policy change. Noteworthy elements include deeply personal narratives, resilience in the face of systemic barriers, and a host who probes for actionable lessons and ongoing impact beyond personal turnaround.
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These podcasts share a similar audience with Nightmare Success In and Out:
1. Crime Junkie
2. Nothing’s Off the Table with Louis Ruggiero
3. Locked In with Ian Bick
4. Betrayal Season 5
5. Court Junkie
Nightmare Success In and Out launched 5 years ago and published 221 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. Doug Feller
2. Kerwin Pittman
3. Jason Pears
4. Ryan Bloom
5. Fox Richardson
6. Rob Richardson
7. Jonathan Schwartz
8. David Carrillo
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