Nightmare Success In and Out

brent cassity
  • 5.0 (206)
  • SOCIETY & CULTURE
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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.

  1. 1D AGO

    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

  2. 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

  3. 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

  4. 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

  5. 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

  6. JAN 29

    From Wall Street High to Rock Bottom: Sean Mueller’s Redemption Story: Fuel To Change

    Sean Mueller built a hedge fund empire from the ground up—without a college degree—raising over $100M and becoming “the guy who never lost money.” But in the pressure-cooker era of Bernie Madoff and Wall Street crackdowns, a string of ethical blind spots and performance-driven decisions led to a securities fraud conviction and a 40-year state prison sentence. In this episode of Nightmare Success In & Out, Sean opens up about the mindset shifts that fueled both his rise and his downfall, the moment everything collapsed, and what it took to rebuild his life from inside prison walls. Today, he’s a summa cum laude graduate, an advocate for prison education, and the author of the upcoming book: After The Walls: Living Without Shortcuts—speaking to leaders, compliance teams, and professional audiences about ethical decision-making under pressure and transforming setbacks into strength. 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 8m

  7. JAN 22

    Sentenced at 16, Free at Last: Cheryl Armstrong on 26 Years in Prison & Planting Purpose

    Cheryl Armstrong’s nightmare began at 16 years old—when she was sentenced to decades in prison and ultimately spent 26 years incarcerated. In this powerful episode of Nightmare Success In and Out, Cheryl takes us inside the reality of surviving nearly three decades behind the wall without losing hope—and the inner transformation that changed everything. Now a two-time international bestselling author, keynote speaker, and founder of Plant Your Energy, Cheryl shares how daily discipline, intentional energy, and radical ownership of your choices can turn even the darkest chapter into purpose. This conversation is about accountability, redemption, and breaking free from the mental prisons that hold so many of us—inside or out. 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 16m

  8. JAN 15

    The Power of One Decision: From Prison to Paychex — Allyssa Baker’s Comeback Story

    Allyssa Baker’s story is the definition of Nightmare Success. What began as a prescription for pain spiraled into addiction, homelessness, and a six-year prison sentence. But behind bars, Allyssa made one decision that changed everything: she refused to quit. She earned her degree with honors, completed recovery work, and fought her way into Televerde—one of the most competitive, highest-paying jobs inside prison—learning elite B2B sales skills while incarcerated. Now an Account Executive at Paychex, Allyssa opens up about the real moments that broke her, the discipline that rebuilt her, and how second chances—combined with relentless accountability—can turn rock bottom into a foundation. This is a masterclass in resilience, reentry, and the quiet power of doing the next right 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!"

    1h 8m
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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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