Nightmare Success In and Out

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:

Surviving War, Cancer, and the DOJ: The Resilient Dr. Rifai Aug 14, 2025

Show notes

In this episode of Nightmare Success, Brent Cassity interviews Dr. Muhamad Ali Rifai, who shares his incredible journey from surviving a war-torn childhood in Syria to facing a federal investigation in the United States. Dr. Rafi survived machine gun fire as a child. He escaped thyroid cancer and a car crash that should have killed him, but nothing prepared him for going to trial with the United States Government. The Doctor discusses his experiences with raw authenticity, the challenges of navigating the legal system, and the importance of telemedicine. Dr. Rifai, who is both an internist and psychiatrist, was a pioneer of telemedicine. He emphasizes the need for professionals to understand the complexities of the law and shares insights from his own trial, where he was ultimately acquitted of all charges. His big "tip" is do not talk to the investigators, they are professionals. Let your attorney handle all communications. The conversation highlights the power of staying true to your beliefs and the importance of supporting others in similar situations. Dr. Rifai is the author of the book Doctor Not Guilty, and he is the founder of SHIELD that helps professionals through the complicated process of being indicted.

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Pamela Winn: Prison to Presidential Lifetime Award Winner Aug 07, 2025

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What makes someone go from "I can't" to "I can" mindset. Pamela Winn's mindset change came from having a conversation with a friend after returning home from a 78 month Federal Prison Sentence. Pamela Winn earned a scholarship to college and later became a registered nurse before her world came crashing down with a charge of mortgage fraud. She had a miscarriage in custody being shackled with a hard fall. Her journey is one of courage, advocacy, and unshakable resolve. After experiencing firsthand the devastating gaps in our criminal justice system, Pamela turned her pain into purpose, founding RestoreHER, a policy and advocacy organization dedicated to ending the mass incarceration of women and addressing the unique challenges justice-impacted women face. Honored with numerous awards for her leadership, including The Presidential Lifetime Achievement Award in 2023, Forbes 50 Over 50 Impact List, and PBS Short Film Festival Winner "Winn Movie" to name a few. Pamela has become a powerful national voice for dignity, health, and human rights. She added language for women incarcerated in the the First Step Act.

In this episode of Nightmare Success In and Out, Brent Cassity sits down with Pamela to explore her personal story, the systemic barriers she’s fighting to dismantle, and the hope she’s building for women across the country.

"From Rock Bottom to Roofing Powerhouse: Brandon James Rewrites His Future" Jul 31, 2025

Show notes

Brandon James walked out of prison over 6 years ago, and has created one of the biggest roofing companies in the state of Missouri. Brandon was stuck at rock bottom who attempted to take his life a few weeks out of prison. This is an incredible redemption comeback story. He says you cannot be a victim and victor at the same time. Brandon became intentional about what he wanted in life. He wrote it down and asked for help. He is now the founder of Brandon J Roofing of one of the fastest growing roofing companies doing over $60 million a year annually. In this episode of Nightmare Success In and Out, Brent Cassity interviews Brandon James, who shares his incredible journey from a troubled childhood and a 10 year incarceration to becoming a successful entrepreneur, podcast host of WIT "Whatever It Takes", and a motivational speaker. The discussion delves into themes of overcoming fears, the impact of early life experiences, the challenges of re-entering society after prison, and the importance of sharing one's story. Brandon is constantly seeking advice from mentors, coaches, and studying the people who have been a success. This episode is full of life lessons of how to get unstuck and act on your purpose.

From Judge to Prison: Jessica O'Brien's Fall and Rise Jul 24, 2025

Show notes

In this powerful and revealing episode of Nightmare Success In and Out, Brent Cassity sits down with former Illinois Judge Jessica O’Brien—the first Filipino-American elected to the bench in Cook County—who went from a respected courtroom authority to a federal inmate. Jessica opens up about her stunning journey through the justice system:the decision to go to trial that led to a conviction for mortgage fraud, the surreal experience of trading her judge robe for a prison uniform, and how she rebuilt her identity from the inside out. With raw honesty, she reflects on the shame, isolation, and loss of purpose she faced, and how she found resilience and redemption in the most unlikely place. Now an advocate for second chances and systemic reform, Jessica shares how her experience has reshaped her understanding of justice—and her mission moving forward. She is still diligently fighting to overturn her conviction. This is a conversation about resilience , surviving, and the courage to rewrite your story. A must-listen for anyone who believes that rock bottom can be the beginning of something new.

Cooking Up a Comeback: Darnell "SuperChef" Ferguson Unfiltered Jul 17, 2025

Show notes

From homelessness to cooking for Team USA at the Olympics, to Food Network fame—Darnell "SuperChef" Ferguson has lived a life of extremes. But behind the fame and fire in the kitchen, his journey has been anything but smooth. In this powerful episode of Nightmare Success: In and Out, Darnell opens up about his early battles with the law, rebuilding his life through food, and the recent legal storm that nearly unraveled everything he worked for. We go deep into his rise from rock bottom, the pressures of success, the realities of public scrutiny, and what redemption means when your past keeps knocking on your door. This is a raw, unfiltered conversation about second chances, staying accountable, and finding purpose through the pain.

"The Fall of a Financial King: The James Catledge Story" Jul 10, 2025

Show notes

James Catledge was once a high-flying investment promoter with a charismatic edge and a growing empire that promised wealth and security. He decided to diversify for his clients in real estate in the Dominican Republic that turned into a nightmare. James shares his incredible journey from a challenging childhood to becoming a successful entrepreneur. James discusses the impact of his early experiences, including his time as a missionary. In this gripping episode of Nightmare Success: In and Out, James opens up about the rise of his financial kingdom, the criminal investigation that turned his world upside down, and what it was like facing the reality of federal indictment and incarceration. Now out of prison, he reflects on the hard lessons learned, the people affected, and the long road to redemption. James has transitioned into a new career in financial services, developing a scoring algorithm to help financial advisors better serve their clients. This is a raw, revealing conversation about character, reputation, justice, and second chances.

From Prison to Properties: The Inspiring Journey of Donald Hinton Jul 03, 2025

Show notes

In this episode of Nightmare Success, Brent Cassity interviews Donald Hinton, who shares his inspiring journey from a troubled childhood to overcoming significant challenges in prison and ultimately finding success in real estate. Donald discusses the impact of his father's incarceration on his life, and the turning point that led him to change his life while in prison. His son came to visit him in the exact same prison visiting room Donald had visited his own dad. He committed he was going to break the cycle. He emphasizes the importance of planning for life after incarceration, the challenges he faced, and how he now helps others by providing housing and mentorship. Donald's story is a testament to resilience, personal growth, and the power of second chances. Check out his book on Amazon: From Prison to Properties.

From Bad Things On The Streets: To Healthy Treats: The Owen Hanson Story Jun 26, 2025

Show notes

A surfer kid from California, Owen Hanson was still in his twenties when he found himself the leader of a multimillion-dollar criminal empire. What began as an attempt to fit in with the rich kids at the University of Southern California soon grew into gambling and loan sharking, which then opened the door to drug trafficking and money laundering. Hanson wasn’t just involved in this stuff—he excelled at it. Living the fast-paced lifestyle of the rich and famous, Hanson was finally gaining the respect he craved. But with the cartel, a serious drug-abuse problem, and the pursuit of the FBI all threatening to overtake him, it wouldn't be long before his glamorous lifestyle caught up with him. It all came to a head with a 21 year Federal Sentence. Instead of wallowing in self pity, Hanson got reinspired with his entrepreneur instincts. He created a protein ice cream in a mop bucket in prison, and California Ice Protein was born. Hanson is ramping up to take California Ice Protein all across the country. If you like comeback stories, sprinkled with words of lived experience for building a business...this is your episode. Find Owen Hanson on social media platforms ⁠ ⁨@theofficialcakid⁩ ⁠ ...get your personal signed copy of his book The California Kid at his website : thecaliforniakid.com

Honored Combat Veteran to Conviction: Jeremy Harrell's Battle with PTSD and the DOJ Jun 19, 2025

Show notes

How does an honored combat veteran who became an expert on PTSD helping so many with the Veterans Club, end up in prison? Jeremy Harrell survived the Iraq War only to return home to a different kind of battlefield—PTSD. Jeremy has been hailed as a leader in veteran advocacy and mental health. He founded the Veterans Club that has been nationally heralded as the leader of veteran PTSD treatment. Jeremy’s world unraveled when he was convicted of veteran benefit fraud with being disabled with PTSD. Jeremy did not diagnose himself of PTSD, no, that was diagnosed by several doctors. Jeremy took his case to trial and lost. Fresh out of federal prison, Jeremy joins us to talk about the fight for his reputation, the realities of navigating the justice system, and why the Bureau of Prisons now sees him as a voice for hope and redemption. This is a raw, honest look at the thin line how good people that are helping people can follow into the justice system abyss. A warrior for criminal justice reform has been awakened: Jeremy Harrell.

Finding Hope in Chaos: The Noah Asher Journey Jun 12, 2025

Show notes

Noah Asher is an award-winning author, podcast host, speaker, and CEO, known for his impactful work surrounding reentry and rehabilitation. His first book, CHAOS, has reached over 1.4 million people, sparking change and inspiring those on the path to purpose and redemption. Through his writing, speaking, and leadership, Noah’s mission is clear: to bring Hope, Help, and Humor to those living in their darkest moments. His unique perspective and passion make him one of the leading voices in the conversation around prison reform and personal transformation. Noah's journey to becoming a change-maker began ten years ago when his life took a dramatic turn. Arrested and struggling with depression, he attempted to take his life in jail. But after surviving that attempt, he realized that while he couldn’t change where he was physically, he could change where he was mentally and spiritually. Today, Noah dedicates his life to helping individuals find purpose in their pain and embrace the power of their past. Life experience wisdom is shared throughout this episode.

Noah's journey to becoming a change-maker began ten years ago when his life took a dramatic turn. Arrested and struggling with depression, he attempted to take his life in jail. But after surviving that attempt, he realized that while he couldn’t change where he was physically, he could change where he was mentally and spiritually.

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