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 were in and now out of prison. What was life like before they went in, life inside prison, and life now that they are back home. These conversations are deep, sad. often funny, but always interesting.
Latest episodes
Showing 20 · updated from the feed
From Wall Street to Federal Prison: How Failure Rebuilt Pierre Rogers
Pierre Rogers rose from childhood poverty to become one of the youngest senior vice presidents at Columbia Management, Bank of America’s asset-management division. By age
Oct 22 1 h 12 min
Dickie Scruggs: King of Torts | From Billions to Federal Prison & Redemption
He was known as the "King of Torts"—one of America's most powerful trial lawyers, who helped take on Big Tobacco in historic multibillion-dollar litigation. Then came a f
Oct 15 1 h 28 min
Life After Prison: Ending the White Collar Life Sentence | Jeff Grant & Drew Chapin
The prison gates open. But does the sentence really end?
Jeff Grant and Drew Chapin join Brent Cassity to explore the lasting consequences of a white collar conviction—f
Oct 5 51 min
The Death Row Artist Who Helped Solve Cold Cases | William Noguera
William “Bill” Noguera was 18 years old when he committed a murder he neither minimizes nor excuses. Sentenced to death, he would spend approximately 42 years incarcerate
Oct 1 1 h 04 min
He Met Him in a Cage on Death Row: William Noguera & Walt Pavlo’s Unlikely Friendship
In 2013, Forbes contributor and former federal prisoner Walt Pavlo walked onto San Quentin’s Death Row and into a cage with William Noguera—a man who had been condemned t
Sep 24 37 min
60 Years in Prison. A Governor’s Pardon. Sam Harris’s Second Chance
Samuel E. Harris went from serving his country in the U.S. Army to battling addiction and receiving a 60-year prison sentence. More than 24 years later, a rare gubernator
Sep 17 59 min
From Addiction and Prison to Award-Winning Journalist | Ryan Moser
Addiction cost Ryan Moser his marriage, his freedom, and precious years with his son. After cycling through juvenile detention and prison, he received a 10-year Florida s
Sep 10 1 h 05 min
“I Ran Out of Tomorrows”: From Luxury Interior Designer to Federal Prison | Jennifer Michele Helm
Jennifer Michele Helm built a successful career designing luxury homes and believed she had finally made it. But behind the beautiful interiors and public image, her busi
Sep 3 1 h 38 min
Sentenced to 40 Years—He Became the Jailhouse Lawyer Who Set Himself Free | Chad Marks
At 24 years old, Chad Marks received a 40-year federal prison sentence. Facing the possibility of spending most of his life behind bars, he began teaching himself the law
Aug 27 1 h 01 min
Wrongfully Convicted: Bruce Bryan Lost 29 Years — But Never Lost Hope | Nightmare Success
Imagine being 23 years old and suddenly facing the possibility that you may never come home.Bruce Bryan wrongfully convicted of murder and sentenced to life in prison. He
Aug 20 48 min
The FBI Knocked—and This Attorney Opened the Door | Stuart Anderson
Stuart Anderson spent more than two decades building a successful career in law and business. Then federal investigators knocked on his door and said they only wanted to
Aug 13 1 h 29 min
The Judge Who Sentenced Him to Life Fought to Set Him Free | Chris L. Young Story
Chris L. Young was only 22 years old when a federal judge sentenced him to two mandatory life sentences without the possibility of parole under federal drug laws.
Most b
Aug 6 1 h 00 min
He Wore the Badge. Then Went to Prison. | Kent McGowen's Story
In this unforgettable episode of Nightmare Success, Brent Cassity sits down with former Harris County Sheriff's Deputy Kent McGowen to hear the story that has defined mor
Jul 30 1 h 46 min
Former Arkansas State Senator Jeremy Hutchinson: Federal Prison, Presidential Pardon & Finding Purpose Again
What happens when your entire life changes overnight?
Former Arkansas State Senator Jeremy Hutchinson appeared to have it all—a successful legal career, a respected posi
Jul 23 1 h 06 min
The Hidden Cost of Gambling Addiction: Dr. Julie Howell opens up about surviving prison
How does a respected university professor lose everything?
Dr. Julie Howell spent decades building a successful career in higher education, earning the respect of collea
Jul 16 1 h 29 min
From Future Baseball Star to 27 Years in Prison: The Two-Time Exoneration of Jimmie Gardner
Exonerated twice. Jimmie Gardner was living his dream as a professional baseball prospect with the Chicago Cubs when a wrongful conviction stole 27 years of his life. Aft
Jul 9 1 h 38 min
Irvin Mayfield Jr.: Grammy Award, Federal Prison & The Comeback Story Nobody Saw Coming
Grammy Award-winning jazz trumpeter Irvin Mayfield Jr. joins Brent Cassity for an unforgettable conversation about success, public failure, federal prison, and rebuilding
Jul 2 1 h 36 min
Death Row to Bestselling Author | Damien Echols on the West Memphis Three, Freedom & Life After Death
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 he
Jun 25 1 h 05 min
From Federal Prison to Fortune 500 Speaker | Rashmi Airan's Incredible Comeback Story
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 sch
Jun 18 1 h 05 min
Mayor, Governor Candidate, Federal Inmate: Scott Maddox's Untold Story
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 At
Jun 11 1 h 24 min
Chart positions
Where Nightmare Success In and Out ranks today in each Apple Podcasts chart (US, Oct 27, 2026).
A curated, balanced selection of Apple Podcasts reviews.
Brent Cassity’s Nightmare Success podcast is an absolute gem! Brent brings powerful stories of transformation and redemption to the forefront, shedding light on the resilience of the human spirit. Each episode showcases individuals who have faced unimaginable challenges—many after time in prison—yet have turned their lives around in ways that inspire hope for anyone feeling stuck or defeated.
What sets this podcast apart is Brent’s authentic and empathetic approach. He creates a space where guests feel safe to share their journeys, triumphs, and lessons, offering listeners a roadmap for finding hope, even in their darkest moments.
The show reminds us that no matter where we’ve been or what we’ve done, there’s always a chance to rewrite our story. It’s engaging, thought-provoking, and deeply encouraging. If you’re looking for a podcast that uplifts and challenges you to believe in second chances, Nightmare Success is a must-listen!
Dr. Jeremy Larson · Dec 2024
I found Brent’s podcast originally while I was incarcerated. I felt so isolated during my time in county jail for 15 months because no one was there on white collar crimes. No one could relate to me. This led to suicide attempts and often time in the SHU. However when I found this podcast it became a serious game changer for me. I simply don’t think I’d be here without Brent’s podcast and his strength that he has shown with his family through his own journey.
It’s hard to put into words how much it helped me during my time in jail. The stories are compelling and often shocking, and they made me reflect on my own choices and the world around me. Listening felt like a form of therapy, providing insight into a world I was part of but didn’t fully understand. It was a reminder that there’s always more to the story and that even in the darkest times, understanding and learning can lead to growth. Thank you for shedding light on this often-overlooked aspect of crime.
Strawberry20162022 · Nov 2024
Brent is doing an important work of bringing light to the pain and brokenness in our community! His easy and relaxed interview approach provides the space necessary for transparency. I love this!
js1146 · Sep 2024
Having been interviewed by Brent, and listened to his other interviews, this is a podcast that should be listened to by everyone. The stories of those who have experienced the criminal justice system and all of its flaws is a must listen.
Evesims · Aug 2024
We strive to present a balanced view by showing a diverse range of reviews from Apple Podcasts.
More podcasts like Nightmare Success In and Out
Popular shows in Society & Culture, for your next listen.
Here you find the Apple Podcasts chart positions of Nightmare Success In and Out, its latest episodes to listen to directly, and reviews from listeners. Rankings are updated daily for the United States.
