brent cassity

Nightmare Success In and Out

Society EN ↓ 234 episodes

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.

Author

brent cassity

Category

Society

Podcast website

www.brentcassity.com

Latest episode

Jul 9, 2026

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Episodes

A Life Sentence, A Path to Redemption: The Lester Young Story 02.01.2025

In this episode of Nightmare Success, host Brent Cassity interviews Lester Young, a former inmate who turned his life around after serving 22 years of a life sentence. Lester is the founder of Path2Redemption a non-profit that helps the formerly incarcerated transition back into society. The organization also has a powerful at-risk youth program. Young is a TEDX Speaker, a Best-Selling Author, and...

Building Second Chances: Sean Stegeman's and Lee Loveall's CMC Journey 19.12.2024

In this episode of Nightmare Success, Brent Cassity interviews Sean Stegeman and Lee Loveall about what it means to value a real second chance after prison. They discuss Sean's journey from a troubled youth to in and out of prison in his twenty's and early thirty's and ultimately finding faith and purpose in life. Lee shares insights on building a successful company, CMC, that builds the buildings...

US Army Combat Vet: PTSD Expert: Federal Prison, The Jeremy Harrell Story 12.12.2024

In this episode of Nightmare Success, host Brent Cassity interviews veteran Jeremy Harrell. Jeremy is a Iraq War Combat Veteran. He was diagnosed with PTSD and became a national expert on the subject. He created Veterans Club INC, that is a nationally recognized non-profit that helps veterans recover from PTSD. How did he get federally indicted? Harrell shares his incredible journey from a challen...

From Montreal to Omaha to Prison: The Wendy Lankton Story 05.12.2024

How does Wendy Lankton go from a wife working in her husbands law firm in Montreal to being arrested in a drug conspiracy in Omaha Nebraska? It is quite the Odessey to what she is doing today. In this episode of Nightmare Success, host Brent Cassity interviews Wendy Lankton, who shares her harrowing journey from addiction to incarceration and eventual recovery. Wendy discusses the impact of the Fe...

Carlos Watson: The Visionary Entrepreneur Railroaded by Injustice 28.11.2024

On this episode of Nightmare Success with Brent Cassity, we explore the shocking and deeply troubling story of Carlos Watson—a pioneering Silicon Valley entrepreneur who built OZY Media from the ground up, transforming it into a near-billion-dollar powerhouse. But in 2019, everything changed. When Watson refused to sell OZY to East Coast competitor Ben Smith (formerly of BuzzFeed)—not once, but fi...

"Dad what were you thinking?" Bill Carlson's Journey from American Dream to Prison 21.11.2024

The call to his daughter explaining how he had committed a white collar crime...her response was, "Dad what were you thinking?" Bill Carlson established his own investment firm naming the firm after his grandfather Victor. He had it all but became blinded by chasing the material things in life. He ended up making a choice that changed his life. In this episode of Nightmare Success, host Brent Cass...

The Nightmare Marriage: The Leah Howard Story 14.11.2024

In this episode of Nightmare Success, host Brent Cassity interviews Leah Howard, who shares her harrowing journey from a troubled marriage to a life-changing incident that led her to prison. Leah discusses her early life, the challenges of her marriage, the stalking she endured, and the climactic moment when she snapped that changed everything. Through her experiences, Leah found her purpose and n...

Founder of Real Estate Empire Falls: Sentenced to Years in Prison at 77 Years Old, John Dimenna 07.11.2024

In this episode of Nightmare Success, host Brent Cassity interviews John Dimenna, a former real estate mogul who sold his commercial real estate empire before the crash of 2008. Many said he was the smartest guy in the business. He says he began to believe it, and he jumped back in the game instead of a comfortable retirement... at 77 years old he was federally convicted to years in prison. John s...

Facing Your Fears: The Journey of Nate Schott 31.10.2024

Could Nate Schott have been the next United States Senator from Tennessee, probably. In this episode of Nightmare Success, host Brent Cassity engages with Nate Scott, who shares his journey from a successful entrepreneurial career in dentistry to facing the consequences of healthcare fraud. Schott was known to buy groceries for folks or letting someone stay rent free to get back on their feet. Nat...

Turning Adversity into Opportunity: Lessons from Good Planet Foods CEO David Israel 24.10.2024

David Israel, a successful serial entrepreneur, shares his journey of overcoming adversity and turning lemons into lemonade. From serving a prison sentence to founding successful companies like Pop Gourmet created from prison, taking the snack industry by storm. The idea originated from inmates who were making their popcorn taste good. Oprah became a raving fan of the product. David then founded a...

Redemption Behind Bars, A Story Of Hope: Jason Holland 17.10.2024

Can a teenager, who commits a murder, find redemption and purpose back in society 28 years later? In this episode of Nightmare Success, host Brent Cassity interviews Jason Holland, who shares his harrowing journey from a life of crime to serving 28 years in prison for a murder that he would give anything to be able to take back that night. Jason's story became a national story covered by Rolling S...

Prostate Cancer In Prison: CEO survives it all, The David Grosky Story 10.10.2024

In this episode of Nightmare Success, host Brent Cassity speaks with David Grosky, a former CEO and attorney who faced a tumultuous journey from corporate success to incarceration. His case went from SEC violations to criminal charges. David shares his experiences of navigating the complexities of the legal system, the emotional toll of losing family members while in prison, and the importance of...

Finding Hope and Transformation in the midst of Desperation: Wesley Keziah 03.10.2024

How does a man arrested 82 times transform his life to help others in a profound way? Wesley Keziah shares his journey from a troubled childhood to addiction and incarceration, and ultimately finding redemption and transformation through faith. He opens up about the challenges he faced growing up in a broken home, being molested, and the impact it had on his mental health. Wesley's addiction led h...

Committing to Change and Rebuilding a Life: The Portia Louder Story 19.09.2024

In this episode of Nightmare Success, Brent Cassity interviews Portia Louder, author of the book Living Louder- A Compassionate Journey Through Federal Prison. Portia shares her incredible journey from a non-traditional upbringing to facing the challenges of teenage motherhood, addiction, and ultimately, a prison sentence for mortgage fraud. Portia's story is one of resilience, transformation,...

Out of Isolation and Into Community: White Collar Conference October 19 17.09.2024

In this episode of the Nightmare Success podcast, Brent Cassity and guests Jeff Grant, founder of White Collar Support Group, and Bill Livolsi, Deputy Director of White Collar Support Group discuss the upcoming White Collar Conference, emphasizing the importance of community and support for individuals affected by white collar crimes. They explore the challenges of reintegration into society, the...

From Nightmare to Success: Augie Ghilarducci's Comeback Story Asking for Help: The Path to a Successful Second Chance 12.09.2024

How did Augie Ghilarducci survive and thrive after serving 13 years in Federal Prison? Augie Ghilarducci is the founder of the Second Opportunity Reentry Program, which provides courses focused on employment readiness, financial literacy, life skills, and reentry. He developed these programs while serving a 13-year sentence in the federal prison system. Augie's story is a true nightmare succes...

The Power of Belief: Kaysia Earley's Redemption Journey from Prison to Powerhouse Attorney 05.09.2024

Could a person go from prison solitary confinement to respected attorney? Kaysia Earley did just that. She was arrested and charged with felony embezzlement during her senior year in college. She was working at a shoe store giving discounts on shoes to friends. Despite being four months pregnant, she was put in solitary confinement. However, this experience didn't break her, but made her stron...

From Wrongful Conviction to Freedom: Duane Williams' Story 29.08.2024

Imagine waking up in your bed with police guns drawn at you. You have no idea why they are there because you are being wrongly accused of murder, a nightmare. Dwayne Williams shares his story of being wrongfully convicted and imprisoned for a crime he didn't commit. The nightmare began when he was arrested and charged with a double murder and arson. Throughout the trial, Dwayne faced numerous...

Finding Hope and Purpose after Prison: The William Sansing Story 22.08.2024

How do you survive the nightmare of losing everything and going to prison? If you are William Sansing you spend the next two decades, post prison, advocating for people of disabilities, people directly impacted by the legal system, and people with substance use disorders. William received a Doctor of Philosophy in Counselor Education/ School Counseling and Guidance Services. He is the author of th...

Private Equity COO risks it all then prison: The Mark Varacchi Story 15.08.2024

It has been said that success on Wall Street can become intoxicating. Mark Varacchi, a 20 year former hedge fund executive, shares his story of how he went from success to standing at the gates of prison. He took responsibility for his actions after building systems and processes identifying flaws and risks in those systems, which eventually led to his downfall. Those skills were clearly used when...

Surviving Sexual and Physical Abuse - Murder of Abuser - The David Garlock Story 08.08.2024

David Garlock shares his story of surviving sexual and physical abuse, eventually he and his brother killed their abuser. The brothers received a 25 year prison sentence. He grew up in a dysfunctional home and experienced multiple traumatic events. At 11 years old, he lost his innocence and had to hide the abuse. David served 13 years in prison and used his experience to advocate for criminal lega...

Wall Street Hedge Fund Founder/Prison to Passion - The Chip Skowron Story 01.08.2024

What happens when a Wall Street Hedge Fund Founder goes to prison. He rises in again to become a force for change of reentry. In this episode of the Nightmare Success In an Out podcast, Brent Cassity interviews Chip Skowron, the CEO of Prison Entrepreneurship Program. Chip shares his journey from being the founder of one the largest Hedge Funds on Wall Street, Frontpoint Partners, to being convict...

All American Running Back Stumbles But Rises Again: The Stephen Barbee Story 25.07.2024

Stephen Barbee's life story is one of dreams, destruction, disgrace, and deliverance. He grew up in a loving Christian home with a pastor father and excelled in sports, particularly football. Stephen earned All-American honors as a college running back. However, he struggled with addiction and eventually found himself homeless and facing a 70 month federal sentence. After getting out of prison...

From Prison to State House Rep - The Tarra Simmons Story 18.07.2024

How does someone go from prison to becoming an attorney, and State Representative? Tara Simmons shares her inspiring story of overcoming adversity and turning her life around after experiencing extreme poverty, substance abuse, and incarceration. She dropped out of middle school at 13, got pregnant at 14, but eventually found her way back to school and graduated high school. She went on to earn a...

A 55 year sentence for a 17yr Old - The Elizabeth Shatswell Story 11.07.2024

Elizabeth Shatswell’s story is one of resilience and a thirst for knowledge after receiving a 55 year prison sentence as a 17 year old. Teenagers have events in their lives they wish they could take back. Elizabeth had a night that involved a robbery and carjacking. The events that followed shows how broken our justice system is for far too many. This inspiring story shows us how you can grow and...

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