Nightmare Success In and Out

brent cassity
  • 5.0 (209)
  • SOCIETY & CULTURE
  • UPDATED WEEKLY

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.

  1. 1D AGO

    From Federal Prison to Entrepreneur | Doug Feller’s Comeback Story :Reentry Truth

    What happens after prison? For most people, that’s where the real struggle begins. In this episode of Nightmare Success In and Out, Brent Cassity sits down with Doug Feller—an entrepreneur who went from building businesses and living fast… to facing federal charges, prison time, and starting over from nothing. Doug shares the truth about reentry that nobody talks about:👉 Why getting out of prison is just the beginning👉 The stigma that follows you for life👉 How he rebuilt from $10/hour jobs to building and selling a company👉 Why he created the MyHarvest App to help others succeed after incarceration “Getting out of prison isn’t the end of the sentence… it’s the beginning of the climb.” This is more than a prison story—it’s a blueprint for resilience, second chances, and rebuilding your life when everything is gone. Show sponsors: Navigating the challenges of white-collar crime? The White-Collar Support Group at Prisonist.org offers guidance, resources, and a community for those affected. Discover support today at Prisonist.org Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount on services to boost your digital image and online reputation. Visit Discoverability.co and secure your online presence today. Skip the hassle of car shopping with Auto Plaza Direct. They’ll handle every detail to find your perfect vehicle. Visit AutoPlazaDirect.com "Your personal car concierge!"

    1h 23m

  2. MAR 26

    From Prisoner to Prison Owner: Kerwin Pittman’s Blueprint for Second Chances

    What happens when your worst fear becomes your reality… and you come back determined to rebuild the very system that once held you? In this powerful episode of Nightmare Success In and Out, Brent Cassity sits down with Kerwin Pittman, a nationally recognized recidivism reduction expert, founder and executive director of Recidivism Reduction Educational Program Services, and the first formerly incarcerated person in U.S. history to purchase a decommissioned prison. Kerwin shares his journey from growing up in poverty and violence, to gang involvement, prison time, solitary confinement, and ultimately a complete transformation from the inside out. He opens up about the moment that changed everything, how he educated himself while incarcerated, and how he came home with a mission to create real second-chance infrastructure. Now, Kerwin is turning a former prison into a recidivism reduction campus focused on workforce development, behavioral health, education, housing support, and opportunity for justice-impacted people. This is a story about redemption, purpose, and what it really means to keep the main thing the main thing. Show sponsors: Navigating the challenges of white-collar crime? The White-Collar Support Group at Prisonist.org offers guidance, resources, and a community for those affected. Discover support today at Prisonist.org Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount on services to boost your digital image and online reputation. Visit Discoverability.co and secure your online presence today. Skip the hassle of car shopping with Auto Plaza Direct. They’ll handle every detail to find your perfect vehicle. Visit AutoPlazaDirect.com "Your personal car concierge!"

    51 min

  3. MAR 19

    From Federal Prison to a Piano: Jason Made Turns a Nightmare Into Music | Jason Pears

    What happens when your worst fear becomes your reality… and you turn it into art? On this episode of Nightmare Success In and Out, host Brent Cassity sits down with musician Jason Pears, known artistically as Jason Made, whose life took an unexpected turn when a PPP fraud case led to a 30-month federal prison sentence. Raised in Fairhope, Alabama, Jason’s life had always been intertwined with music—from teaching himself piano in church as a child to writing songs in Nashville and Los Angeles. But financial pressures, entrepreneurship, and a pandemic-era business decision eventually led him into the federal justice system. What happened next is the heart of this story. Inside Federal Prison Camp Pensacola, Jason found an unlikely refuge: a chapel piano and a spiral notebook. Over the course of his sentence, he wrote more than 40 original songs, turning isolation, uncertainty, and reflection into deeply personal music. Jason Made's music can be heard on Spotify https://open.spotify.com/artist/6YIPePfcIWGBLFqICgmHYv In this powerful conversation, Brent and Jason discuss: The moment the FBI showed up at his door Navigating the psychological toll of waiting for sentencing Life inside federal prison Finding purpose in unexpected places How music became his path to redemption The creation of his debut EP “Go Lay Down” Jason’s story is a reminder that sometimes your purpose finds you—even in the darkest places. And sometimes, a nightmare becomes the soundtrack to a brand-new life. Show sponsors: Navigating the challenges of white-collar crime? The White-Collar Support Group at Prisonist.org offers guidance, resources, and a community for those affected. Discover support today at Prisonist.org Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount on services to boost your digital image and online reputation. Visit Discoverability.co and secure your online presence today. Skip the hassle of car shopping with Auto Plaza Direct. They’ll handle every detail to find your perfect vehicle. Visit AutoPlazaDirect.com "Your personal car concierge!"

    1h 14m

  4. MAR 12

    All Charges Dismissed: Ryan Bloom’s 18-Month DOJ Nightmare

    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 front yard, an 18-month federal ordeal, and a legal fight that threatened to destroy everything he had built. But this story takes a turn almost nobody ever sees. After relentless research, the right legal team, and the courage to fight back, all charges against Ryan were dismissed. This is a powerful conversation about fear, family, resilience, justice, and what it takes to stand your ground when the full weight of the government is pressing down on you. This episode is for anyone facing adversity, navigating the criminal justice system, or looking for proof that persistence and courage still matter. Show sponsors: Navigating the challenges of white-collar crime? The White-Collar Support Group at Prisonist.org offers guidance, resources, and a community for those affected. Discover support today at Prisonist.org Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount on services to boost your digital image and online reputation. Visit Discoverability.co and secure your online presence today. Skip the hassle of car shopping with Auto Plaza Direct. They’ll handle every detail to find your perfect vehicle. Visit AutoPlazaDirect.com "Your personal car concierge!"

    1h 19m

  5. MAR 5

    Fox & Rob Richardson: 21 Years as an Incarcerated Family | TIME Documentary, Angola Prison, Clemency & Redemption

    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 featured in the award-winning documentary ** TIME **. Fox and Rob share the true story of surviving as an incarcerated family—raising six sons, enduring separation, and navigating the Louisiana justice system after Rob received a 61-year sentence and was sent to Angola Prison. They break down what the documentary couldn’t fully show: the pressure on marriage, the emotional cost on children, the grit required to keep hope alive, and the legal fight that ultimately led to freedom. Today, Fox and Rob continue their mission through Participatory Defense Movement NOLA (an initiative of Rich Family Ministries)—training families to become powerful advocates and helping save years of incarceration by organizing community-based defense. If you’ve ever wondered how families survive prison, how clemency happens, or what real redemption looks like—this episode is for you. 📌 Watch/Listen, then drop a comment: What part of Fox & Rob’s story hit you the hardest?✅ Subscribe for more stories of survival, accountability, and second chances. Show sponsors: Navigating the challenges of white-collar crime? The White-Collar Support Group at Prisonist.org offers guidance, resources, and a community for those affected. Discover support today at Prisonist.org Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount on services to boost your digital image and online reputation. Visit Discoverability.co and secure your online presence today. Skip the hassle of car shopping with Auto Plaza Direct. They’ll handle every detail to find your perfect vehicle. Visit AutoPlazaDirect.com "Your personal car concierge!"

    1h 4m

  6. FEB 26

    He Managed Beyoncé & Mariah… Then Stole Millions: Jonathan Schwartz’s Comeback Story

    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 brutal cocaine and gambling addiction that spiraled into embezzling millions from celebrity clients and ultimately led to a six-year prison sentence. In this raw conversation with host Brent Cassity, Jonathan breaks down the roots of addiction, the moment everything collapsed, what prison taught him about accountability and consequences, and how recovery rebuilt his life. Now approaching 10 years sober, Jonathan serves as a Program Director at Altus Rehab, helping others fight the demons that nearly destroyed him. This is a powerful story about secrecy, shame, responsibility—and redemption one day at a time. Show sponsors: Navigating the challenges of white-collar crime? The White-Collar Support Group at Prisonist.org offers guidance, resources, and a community for those affected. Discover support today at Prisonist.org Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount on services to boost your digital image and online reputation. Visit Discoverability.co and secure your online presence today. Skip the hassle of car shopping with Auto Plaza Direct. They’ll handle every detail to find your perfect vehicle. Visit AutoPlazaDirect.com "Your personal car concierge!"

    55 min

  7. FEB 19

    Sentenced to Life Without Parole at 19 | How David Carrillo Earned an MBA in Prison & Won Clemency

    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 defining moment: would he let prison define him… or transform him? Instead of surrendering to despair, David chose radical accountability. He earned his associate’s degree, bachelor’s degree, and MBA while incarcerated. He became the first incarcerated adjunct college professor in the nation, teaching other inmates while serving a life sentence. He mentored men, built programs, and rebuilt himself from the inside out. After 31 years behind bars, David was granted clemency. This episode explores: ​Gang culture and growing up in trauma​Life inside maximum security and solitary confinement​Radical ownership and personal transformation​The power of education in prison​Losing his son and father while incarcerated​Faith, forgiveness, and redemption​What freedom feels like after 31 yearsThis isn’t a story about excuses.It’s about responsibility, growth, and refusing to let your worst decision define your entire life. 📘 Book: Kiko: From Life Without Parole to Life With Purpose Show sponsors: Navigating the challenges of white-collar crime? The White-Collar Support Group at Prisonist.org offers guidance, resources, and a community for those affected. Discover support today at Prisonist.org Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount on services to boost your digital image and online reputation. Visit Discoverability.co and secure your online presence today. Skip the hassle of car shopping with Auto Plaza Direct. They’ll handle every detail to find your perfect vehicle. Visit AutoPlazaDirect.com "Your personal car concierge!"

    2h 1m

  8. FEB 5

    Pageant Queen to Drug QueenPin to Purpose — Jennifer Rogers’ Fenced In No More

    Jennifer Rogers’ story is a full-blown roller coaster—small-town “perfect life,” cheerleading and pageants, then addiction, meth dealing, custody loss, and a federal sentence that forced her to face everything she tried to outrun. In this episode, Jennifer opens up about the double life, the turning points, and the moment she finally realized: it’s you vs. you. Now the founder of the National Women’s Prison Reform Coalition, the visionary behind Rise Up Media, host of the Fenced In podcast, and author of The You Within, Jennifer shares what recovery really took, how she rebuilt her career through sales, and the spiritual shift that helped her reclaim her identity—and her life. Show sponsors: Navigating the challenges of white-collar crime? The White-Collar Support Group at Prisonist.org offers guidance, resources, and a community for those affected. Discover support today at Prisonist.org Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount on services to boost your digital image and online reputation. Visit Discoverability.co and secure your online presence today. Skip the hassle of car shopping with Auto Plaza Direct. They’ll handle every detail to find your perfect vehicle. Visit AutoPlazaDirect.com "Your personal car concierge!"

    1h 48m
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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.

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