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Artwork for Nightmare Success In and Out

Nightmare Success In and Out

brent cassity
White Collar Crime
White Collar Conference
Community Support
Prison Reform
Duane Williams
Reentry After Incarceration
Isolation and Recovery
Wrongful Convictions
Resilience
Networking
Domestic Violence
Wayne County Prosecutor's Office Integrity Unit
Redemption Stories
Mental Health
Redemption
The Cooley Innocence Project
Overcoming Adversity
Entrepreneurship
Criminal Justice System
Second Opportunity Reentry Program

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

PublishesWeeklyEpisodes221Founded5 years ago
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Society & Culture

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Artwork for Nightmare Success In and Out

Latest Episodes

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

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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

YouTube

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

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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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Recent Guests

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
Rob Richardson
Co-author of Time, advocate, and co-founder of related initiatives
Percipitory Defense Movement / Rich Family Ministries
Episode: Fox & Rob Richardson: 21 Years as an Incarcerated Family | TIME Documentary, Angola Prison, Clemency & Redemption
Jonathan Schwartz
Former Hollywood business manager for celebrities; recovering addict and therapist
Altus Rehab / former business manager in entertainment
Episode: He Managed Beyoncé & Mariah… Then Stole Millions: Jonathan Schwartz’s Comeback Story
David Carrillo
Author of Kiko, Life Without Parole to Life With Purpose
Author; former inmate; advocate
Episode: Sentenced to Life Without Parole at 19 | How David Carrillo Earned an MBA in Prison & Won Clemency
Jennifer Rogers
Founder of National Women's Prison Reform Coalition; Rise Up Media founder; author and sales trainer
Rise Up Media; National Women's Prison Reform Coalition
Episode: Pageant Queen to Drug QueenPin to Purpose — Jennifer Rogers’ Fenced In No More

Host

Brent Cassity
Host of Nightmare Success In and Out

Reviews

5.0 out of 5 stars from 301 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 States11 days 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 States12 days 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 States12 days 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 States14 days 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 States14 days 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

Talking Points

Recent interactions between the hosts and their guests.

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.
From Prison to Properties: The Inspiring Journey of Donald Hinton
Q: How did you close your first real estate deal after getting out?
I found a property being sold by a tired owner during COVID, offered $25,000 even though it was worth more, bought it on contract and used a balloon payment to pay back, then partnered with my girlfriend to take on more deals and build a portfolio.
From Prison to Properties: The Inspiring Journey of Donald Hinton
Q: You mentioned planning for a new beginning after release. What concrete steps did you take to prepare while still in the system?
I wrote down a clear plan for what I would do after release, focused on stock market, real estate, and using newspapers to map out new opportunities in Davenport, while avoiding past environments and learning about local property options.
Injustice for a 17 year old girl: The Sheena Eastburn Story
Q: What role did mentors and organizations play in your transformation and reentry journey?
Sheena credits dream.org, Missouri Justice Coalition, and Human Rights Watch-affiliated groups for teaching her to organize, advocate, and convert personal trauma into public service, culminating in leadership roles and policy work.
Injustice for a 17 year old girl: The Sheena Eastburn Story
Q: Walk us through that moment when your life pivoted after learning you could be released and how you kept hope alive.
Sheena describes a long arc of “almost there” moments, the support from advocates, and the emotional turning point when she finally believed freedom could come, even after decades in prison; she emphasizes education, perseverance, and building advocacy networks as the core of that change.

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. Nothing’s Off the Table with Louis Ruggiero
3. Locked In with Ian Bick
4. Betrayal Season 5
5. Court Junkie

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

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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What guests have appeared on Nightmare Success In and Out?

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

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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