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Nightmare Success In and Out

brent cassity
White Collar Crime
White Collar Conference
Community Support
Prison Reform
Duane Williams
Isolation and Recovery
Reentry After Incarceration
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

PublishesWeeklyEpisodes217Founded4 years ago
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Society & Culture

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Artwork for Nightmare Success In and Out

Latest Episodes

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

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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

YouTube

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

YouTube

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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Key Facts

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Recent Guests

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
Sean Mueller
Hedge fund manager, author, and lecturer on ethics and leadership
Mueller Capital / Author of Fuel to Change
Episode: From Wall Street High to Rock Bottom: Sean Mueller’s Redemption Story: Fuel To Change
Cheryl Armstrong
Two-time international best-selling author, keynote speaker, founder of Plant Your Energy
Plant Your Energy
Episode: Sentenced at 16, Free at Last: Cheryl Armstrong on 26 Years in Prison & Planting Purpose
Allyssa Baker
Former incarcerated individual who became an account executive at Paychex
Paychex
Episode: The Power of One Decision: From Prison to Paychex — Allyssa Baker’s Comeback Story
Tom Hardin
Author and former FBI informant on insider trading, aka Tipper X
Tipper X / Wired on Wall Street
Episode: Wired on Wall Street: Tom Hardin (Tipper X) on Wearing a Wire and Surviving the Sting

Host

Brent Cassity
Host of Nightmare Success In and Out

Reviews

5.0 out of 5 stars from 300 ratings
  • A Podcast To See!

    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!!

    Apple Podcasts
    5
    Plant Your Energy Interview
    United States22 days ago
  • Great Podcast with an even better host!

    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

    Apple Podcasts
    5
    Big sarge 1981
    United States6 months ago
  • Smart, engaging, and real!

    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.

    Apple Podcasts
    5
    Baseball_Mom13
    United States6 months ago
  • I would give a 10 star if I could 🌟

    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!!!!! ⭐️✨💫

    Apple Podcasts
    5
    Mrs.Trisha
    United States6 months ago
  • Edge of my seat

    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.

    Apple Podcasts
    5
    Mikki RayeRaye
    United States6 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.

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Talking Points

Recent interactions between the hosts and their guests.

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.
From Bad Things On The Streets: To Healthy Treats: The Owen Hanson Story
Q: How did you handle the fear and keep going through the long prison sentence?
He emphasizes breaking the time into quarters, maintaining focus on short-term goals, education, and eventually channeling energy into building a new brand and writing a book while incarcerated.

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?

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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How many subscribers and views does Nightmare Success In and Out have?

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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. The Shawn Ryan Show
2. Locked In with Ian Bick
3. This American Life
4. Real Time with Bill Maher
5. Prof G Markets

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

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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What guests have appeared on Nightmare Success In and Out?

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

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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