Nightmare Success
Nightmare Success is a podcast created and hosted by Brent Cassity, a former successful entrepreneur who served a federal prison sentence and now focuses on helping others navigate incarceration and reentry into society. The show centers on personal transformation, resilience, and the hidden realities of the American justice system, often featuring guests who have experienced prison firsthand—either as former inmates, family members, or professionals in the legal, corrections, or advocacy spaces.
Overview & Format
Launched in the early 2020s, Nightmare Success takes its name from the term Cassity uses to describe the disorienting, life-altering experience of going from a life of outward success to serving time in federal prison. The show mixes personal storytelling, interviews, and commentary to shed light on the challenges and opportunities that come with life after incarceration.
Each episode typically runs around 60 minutes and follows an interview-based format. Cassity begins with a short introduction, often tying the guest’s story to a broader theme—like loyalty, redemption, betrayal, or resilience. He then dives into a candid conversation with the guest, using his own experience as a foundation for thoughtful, empathetic dialogue. The tone is informal but purposeful, allowing space for both raw emotion and practical advice.
Host
Brent Cassity, formerly the CEO of a national funeral and insurance services company, pleaded guilty to fraud and served a five-year sentence in federal prison. After his release, he began using his platform to share stories from the incarcerated and formerly incarcerated, aiming to reduce stigma and inspire hope. His own story, chronicled in the book Nightmare Success: Loyalty, Betrayal, Life Behind Bars, Adapting, and Finally Breaking Free, forms the philosophical foundation for the podcast.
Notable Episodes
- Richard Bronson: Once associated with Stratton Oakmont, Richard reflects on his time in prison and his subsequent initiative, 70 Million Jobs, aimed at helping formerly incarcerated individuals find employment opportunities.[1]
- Drew Chapin: A tech startup entrepreneur who discusses the challenges of rebuilding after legal setbacks, emphasizing the lessons learned about ethics in entrepreneurship and how to prevent ethical fading in business organizations.[2]
- Jeremy Harrell: A U.S. Army veteran and founder of Veterans Club Inc., Jeremy discusses his mission to support fellow veterans, particularly those facing incarceration, and his efforts to provide resources for successful reintegration.[3]
- Amy Nelson: The founder of The Riveter, she delves into her experience with the legal system, highlighting the personal and professional impacts of her husband’s legal battles and her advocacy for systemic reform.[4]
- Brad Rouse: A former professional involved in financial services, Brad shares insights into the consequences of white-collar crime and his path to redemption and community service post-incarceration.[5]
- Carlos Watson: Founder of OZY Media who shared his perspective on facing legal challenges and media scrutiny. He discusses the impact of these experiences on his life and career, offering insights into resilience and the pursuit of justice.[6]
Important Links
- Nightmare Success on Apple Podcasts
- Nightmare Success on Spotify
- Nightmare Success on Substack
- Nightmare Success on YouTube
Categories
References
- ↑ https://www.youtube.com/watch?v=cAgQk_ocemc
- ↑ https://chapin.io/podcast-nightmare-success-when-your-worst-fears-become-reality/
- ↑ https://nightmaresuccess.substack.com/p/us-army-combat-vet-ptsd-expert-federal-8dc?utm_source=publication-search
- ↑ https://nightmaresuccess.substack.com/p/the-family-struggle-battling-the-716?utm_source=publication-search
- ↑ https://nightmaresuccess.substack.com/p/the-brad-rouse-story-how-does-a-broadway?utm_source=publication-search
- ↑ https://nightmaresuccess.substack.com/p/carlos-watson-the-visionary-entrepreneur-b43?utm_source=publication-search