Nightmare Success In and Out

brent cassity
  • 5.0 (205)
  • SELF-IMPROVEMENT
  • 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

    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

  2. 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

  3. 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

  4. 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

  5. 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

  6. JAN 8

    Wired on Wall Street: Tom Hardin (Tipper X) on Wearing a Wire and Surviving the Sting

    Tom Hardin—better known as Tipper X—went from Wharton to hedge funds, then into a nightmare that turned into one of the most shocking comeback stories on Wall Street. After getting pulled into the world of insider trading, Tom was approached by the FBI and became a covert cooperator in Operation Perfect Hedge, helping build more than 20 cases in what became the largest insider-trading investigation of a generation. In this episode, Tom takes us inside the real-life thriller: the pressure, the rationalizations, the moment the FBI confronted him, and what it’s actually like to wear a wire and get people talking. We also talk about the cost to family, reputation, and identity—and how Tom rebuilt his life into a global speaking career focused on ethics, compliance, and staying off the slippery slope. Preorder / learn more: Tom’s book Wired on Wall Street (out February 2026) and his work as Tipper X. Go to tipperx.com 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 18m

  7. JAN 1

    From Film Sets to Federal Charges: John Santilli Surviving the System

    Filmmaker and producer John Santilli joins Brent Cassity to share a story that goes way beyond Hollywood credits. From working on projects tied to major studio releases to building his career through grit and relationships, John seemed to be living the dream—until a complex business deal spiraled into a federal securities fraud case, a public arrest, and years of legal chaos. In this raw conversation, John walks through what it felt like to watch his reputation collapse, how fear and isolation hit his family, and what it took to survive the mental grind of being overcharged, misunderstood, and pressured into plea deals. He opens up about the raid on his home, the harsh realities of the system, and the rare moment that changed everything: a judge who actually looked at him like a human being. This is a nightmare-to-meaning comeback story about accountability, perspective, resilience, and rebuilding a life—one piece 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!"

    1h 32m

  8. 12/18/2025

    “Duke Got Life: Boxer Charles Duke Tanner’s Journey from Two Life Sentences to Freedom”

    Former undefeated boxing star Charles Duke Tanner went from ESPN and Angelo Dundee’s gym to two life sentences in federal prison for a first-time, nonviolent drug conspiracy. Sixteen years later, he walked out of prison with a presidential clemency in 2020 and a full pardon in 2025. In this powerful episode of Nightmare Success In and Out, Brent Cassity sits down with Duke to unpack a story that feels like a movie script—but it’s all real. Duke shares what it was like growing up in Gary, Indiana during the crack epidemic, becoming a rising boxing phenom, and how money pressures pulled him into a drug conspiracy that changed his life. He talks about hearing the words “two life sentences” in federal court, walking into a maximum-security prison at 24, and the mindset it took to keep hope alive when the system said he would die behind bars. Inside, Duke became a leader—mentoring men, strengthening his faith, and being a present father to his son through letters, calls, and visits. He describes the moment he learned President Trump had granted him clemency, what it felt like to hug his son at the airport for the first time as a free man, and how he’s now using his second chance to fight for others. Today, Duke is co-building Legacy Impact Group with Adam Clausen, serving as VP of Community Affairs for Engineered Tax Services non-profit group, helping justice-impacted entrepreneurs and nonprofits get grant ready, and advocating for the Safer Supervision Act and real second chances. Grab Duke’s book “Duke Got Life” on Amazon — this story needs to be in your hands.If you’ve ever wondered how someone can lose everything, hold onto hope, and come back with purpose—this conversation will stay with you. 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
See All (214)

Trailer

5
out of 5
205 Ratings

About

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.

Information