
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 | 217 | Founded | 4 years ago |
|---|---|---|---|---|---|
| Number of Listeners | Category | Society & Culture | |||

In this gripping episode of Nightmare Success In and Out, Brent Cassity sits down with Ryan Bloom to tell one of the most shocking stories ever featured on the show. Ryan shares how his life was turned upside down by a gunpoint FBI arrest in his fron... more
What happens when your worst fear becomes your reality—and it lasts 21 years?
In this unforgettable episode of Nightmare Success In and Out, host Brent Cassity interviews Sibil “Fox” Richardson and Robert “Rob” Richardson, the New Orleans couple fea... more
Jonathan Schwartz was Hollywood’s go-to financial manager—nicknamed the “Diva Whisperer”—trusted by some of the biggest names in entertainment, including Beyoncé, Mariah Carey, and Alanis Morissette. But behind the scenes, Jonathan was fighting a bru... more
David Carrillo was sentenced to life without the possibility of parole at just 19 years old — for a gang-related murder where he wasn’t the trigger man.
After spending years in maximum security prisons and solitary confinement, David faced a definin... more
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I am so grateful that I was able to be a guest on this podcast! Brent has an amazing platform that gives a voice to those who have been through incredible transformations in their lives. These stories are empowering and inspiring. Thank you Brent for what you do!!
As a guest and as a consumer, I love this podcast! Week after week, Brent is sharing the stories of such inspiring guests. This isn’t just a podcast that you listen to during your commute, this is a podcast that inspires, educates, and empowers listeners as they hear from those who have lived their worst nightmare and bounced back. Additionally, Brent is a great host as he always has such profound questions while giving his guests the opportunity to tell their story. This one is 10/10 and I enco... more
This podcast is a powerful reminder of the strength of the human spirit. Each episode shares real stories of people who have turned devastation into growth and success. It’s moving, uplifting, and leaves me feeling hopeful every time I listen.
Brent’s interviews with his guests are easily a 10 star rating 🤩!!! I tune-in weekly and I can’t wait for what the next podcast will discuss. The topics are very interesting, educational and thought provoking. You will want to subscribe and be a regular listener….I LOVE Brent’s podcast interviews and you will too!!!!! ⭐️✨💫
I just love the way this man interviews. He keeps me at the edge of my seat! The people he brings on his podcast are remarkable, and he special talent with the way he helps people tell their stories.
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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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1. The Shawn Ryan Show
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4. Real Time with Bill Maher
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Nightmare Success In and Out launched 4 years ago and published 217 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. Fox Richardson
2. Rob Richardson
3. Jonathan Schwartz
4. David Carrillo
5. Jennifer Rogers
6. Sean Mueller
7. Cheryl Armstrong
8. Allyssa Baker
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