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Artwork for Nightmare Success In and Out

Nightmare Success In and Out

brent cassity
White Collar Crime
Prison Reform
Wrongful Convictions
White Collar Conference
Community Support
Entrepreneurship
Criminal Justice System
Duane Williams
Reentry After Incarceration
Isolation and Recovery
Reentry
Leavenworth
Resilience
Mental Health
Domestic Violence
Networking
Redemption
Reentry Programs
Addiction
Wayne County Prosecutor's Office Integrity Unit

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

PublishesWeeklyEpisodes233Founded5 years ago
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Society & Culture

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Artwork for Nightmare Success In and Out

Latest Episodes

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

YouTube

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

YouTube

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Recent Guests

Rasmi Airan
Ivy League-educated attorney, federal prisoner, and global keynote speaker
Author of All Rise; leadership speaker
Episode: From Federal Prison to Fortune 500 Speaker | Rashmi Airan's Incredible Comeback Story
Scott Maddox
Former mayor of Tallahassee, Florida; political figure
Former Florida politician
Episode: Mayor, Governor Candidate, Federal Inmate: Scott Maddox's Untold Story
Desmond Meade
Advocate for voting rights and former homelessness survivor
Florida Rights Restoration Coalition (FRSC) / Let My People Vote
Episode: From Homelessness to the Time 100 List | Desmond Meade's Incredible Redemption Story
Kalise White
Author and trauma advocate who discusses her life, trauma, and healing journey
Author, Trauma Advocate
Episode: From Silence to Strength: Kalise White’s Justice-Impacted Comeback Story
Gordie Ernst
Former Georgetown tennis coach involved in the Varsity Blues scandal
Georgetown University
Episode: The Golden Boy, Varsity Blues & Prison: Gordie Ernst’s Fall and Fight Back
Mike Castillero
Founder of StraightPath Venture Partners, pre-IPO investor advocate
StraightPath Venture Partners
Episode: Pre-IPO Millions, Federal Conviction & Fighting Back | Michael Castillero on Nightmare Success
Kelly Givens
Former credit union president, TikTok storyteller
Convicted and Climbing
Episode: She Was a Credit Union President… Then the FBI Showed Up | Kelly Givens’ Story
PJ Jensen
Founder of the LFG Life Podcast; recovery advocate and former executive
LFG Life Podcast
Episode: From Federal Prison to $78M Business: PJ Jensen on Addiction, Discipline & No-Excuses Recovery
Juliet Jacobs
Author of Ambition Addiction; justice-impact survivor; behavioral therapist and recovery coach
Author of Ambition Addiction; recovery professional
Episode: Ambition Addiction: When Success Becomes Your Downfall | Juliet Jacobs

Host

Brent Cassity
Host of Nightmare Success In and Out; leads conversations with justice-system impacted guests about life before, during, and after prison.

Reviews

5.0 out of 5 stars from 331 ratings
  • We Are Not Our Worst Mistake

    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.

    Apple Podcasts
    5
    Setting Failure
    United States3 months ago
  • An Honest and Essential Podcast

    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.

    Apple Podcasts
    5
    J.Anthony2
    United States3 months ago
  • Truth is where real change begins

    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

    Apple Podcasts
    5
    JS Gratitude
    United States3 months ago
  • Silent Exoneration

    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

    Apple Podcasts
    5
    Rd__bloom
    United States3 months ago
  • A great host and a powerful platform ⭐️⭐️⭐️⭐️⭐️

    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

    Apple Podcasts
    5
    ItsJasonMade
    United States3 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Shows authenticity and compassion in telling reform stories.
Host asks thoughtful follow-ups that pull out practical lessons.
Narratives emphasize hope, accountability, and structured reintegration.

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Sword and ScaleSword and Scale
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Behind the BastardsCool Zone Media and iHeartPodcasts
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Modern Wisdom
Modern WisdomChris Williamson

Talking Points

Recent interactions between the hosts and their guests.

Mayor, Governor Candidate, Federal Inmate: Scott Maddox's Untold Story
Q: What was your mindset going into the federal prison system?
He describes a mix of trepidation and resolve, detailing the transit, the confinement, and the realization that the experience would test his character, not just legally but personally and emotionally.
Pre-IPO Millions, Federal Conviction & Fighting Back | Michael Castillero on Nightmare Success
Q: What was the experience like inside the courtroom during the trial?
The trial spanned about two and a half weeks, with daily expectations of victory that steadily gave way to a verdict of guilt on all accounts after complex jury instructions and a massive document load.
Pre-IPO Millions, Federal Conviction & Fighting Back | Michael Castillero on Nightmare Success
Q: Why did you decide to go to trial rather than accept a plea?
The decision came from a belief that pleading would involve lying or compromising their stance; they chose to fight to prove they were not investment advisors and to defend the integrity of their operation.
Pre-IPO Millions, Federal Conviction & Fighting Back | Michael Castillero on Nightmare Success
Q: What happened when the government started to tighten its grip on the case?
The case escalated from civil scrutiny to an aggressive federal investigation; asset seizures followed, and the defendants faced the prospect of a lengthy trial and severe forfeiture, with lawyers negotiating and preparing for possible outcomes.
Ambition Addiction: When Success Becomes Your Downfall | Juliet Jacobs
Q: What inspired you to write Ambition Addiction and explore ambition as a potential addiction?
I observed how ambition, when coupled with a need to always look successful, could escalate into unethical choices. By writing, I could dissect these dynamics, share case studies, and offer a framework for recognizing when ambition crosses into compulsion and how to reclaim one's true self.

Audience Metrics

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Frequently Asked Questions About Nightmare Success In and Out

What is Nightmare Success In and Out about and what kind of topics does it cover?

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.

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Which podcasts are similar to Nightmare Success In and Out?

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

How many episodes of Nightmare Success In and Out are there?

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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What guests have appeared on Nightmare Success In and Out?

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

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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