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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
Resilience
Mental Health
Domestic Violence
Networking
Redemption
Reentry Programs
Addiction
Wayne County Prosecutor's Office Integrity Unit
Redemption Stories

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

PublishesWeeklyEpisodes226Founded5 years ago
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Society & Culture

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Artwork for Nightmare Success In and Out

Latest Episodes

What happens when everything you built comes crashing down?

On this episode of Nightmare Success In and Out, host Brent Cassity sits down with Michael Castillero, co-founder of StraightPath Venture Partners, a pre-IPO investment firm that exploded i... more

YouTube

What happens when a career built on trust… ends in a federal conviction?

In this episode of Nightmare Success In and Out, Brent sits down with Kelly Givens, a former credit union executive whose life changed overnight when accounting mistakes and a ... more

YouTube

What happens when innovation collides with power?

On this episode of Nightmare Success In and Out, Brent Cassity sits down with entrepreneur Steve Keller, a man who built a multi-billion-dollar empire by revolutionizing the life settlement industry—... more

YouTube

What happens when addiction leads you to federal prison—but doesn’t break you?

In this episode of Nightmare Success In and Out, Brent Cassity talks with PJ Jensen, host of the LFG Life Podcast, about his journey through addiction, prison, and rebuil... more

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Recent Guests

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
Doug Feller
Entrepreneur and founder of Superior Asphalt; creator of MyHarvest App
Superior Asphalt; MyHarvest App
Episode: From Federal Prison to Entrepreneur | Doug Feller’s Comeback Story :Reentry Truth
Kerwin Pittman
Founder and Executive Director of Recidivism Reduction Educational Program Services
Recidivism Reduction Educational Program Services
Episode: From Prisoner to Prison Owner: Kerwin Pittman’s Blueprint for Second Chances
Jason Pears
Musician, also known as Jason Made
Go Lay Down project / Jason Made Music
Episode: From Federal Prison to a Piano: Jason Made Turns a Nightmare Into Music | Jason Pears
Ryan Bloom
Guest on the show; testified about his federal case and its resolution
Business owner ( Oklahoma-based construction/utility services)
Episode: All Charges Dismissed: Ryan Bloom’s 18-Month DOJ Nightmare
Fox Richardson
New Orleans-based advocate and co-author of Time, and advocacy leader
Percipitory Defense Movement / Rich Family Ministries
Episode: Fox & Rob Richardson: 21 Years as an Incarcerated Family | TIME Documentary, Angola Prison, Clemency & Redemption

Host

Brent Cassity
Host of Nightmare Success In and Out

Reviews

5.0 out of 5 stars from 309 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 States2 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 States2 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 States2 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 States2 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 States2 months ago

Listeners Say

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

Listeners value the host's empathy and thoughtful questions that encourage guests to share meaningful insights.
The show is praised for inspiring stories of redemption and practical takeaways for reentry and advocacy.
Fans appreciate high-quality interviews that balance hard topics with hopeful, actionable guidance.

Top Society & Culture Podcasts

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The Determined Society with Shawn French | Mindset, Adversity & GrowthShawn French | Adversity & Determination Expert
This American Life
This American LifeThis American Life
Behind the Bastards
Behind the BastardsCool Zone Media and iHeartPodcasts
Sword and Scale
Sword and ScaleSword and Scale
If Books Could Kill
If Books Could KillMichael Hobbes & Peter Shamshiri

Talking Points

Recent interactions between the hosts and their guests.

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.
All Charges Dismissed: Ryan Bloom’s 18-Month DOJ Nightmare
Q: What was the turning point when the case began to shift toward resolution?
The critical shift happened after the AUSA was disqualified, new prosecutors took over, and Bloom's legal team presented compelling evidence and strategy, leading to a real chance of dismissal and a supervised resolution.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

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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?

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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Which podcasts are similar to Nightmare Success In and Out?

These podcasts share a similar audience with Nightmare Success In and Out:

1. Crime Junkie
2. The Girlfriends: Trust Me Babe
3. Dateline NBC
4. 20/20
5. Matthew Cox | Inside True Crime Podcast

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

Nightmare Success In and Out launched 5 years ago and published 226 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. Mike Castillero
2. Kelly Givens
3. PJ Jensen
4. Juliet Jacobs
5. Doug Feller
6. Kerwin Pittman
7. Jason Pears
8. Ryan Bloom

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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