Nightmare Success In and Out

brent cassity
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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. 2D AGO

    “From Life Sentence to Leader: Yusef Wiley’s 100% Turnaround”

    At 21, Yusef Andre Wiley was sentenced to life in a California prison after growing up in the gang-ridden streets of South Central Los Angeles. After surviving violence, a year in solitary, and a near-fatal run-in with a tower guard, a single letter from his father sparked a complete 180° turn. In this episode of Nightmare Success In and Out, Brent Cassity and Yusef walk through the journey from life sentence to reentry leader, creating self-help programs inside prison and later founding Timelist Group, a reentry and housing nonprofit helping formerly incarcerated people with jobs, housing, education, and community. He is the author of the book "If I Knew Then." If you’ve ever wondered whether real change is possible after a long sentence, this conversation is a masterclass in hope, responsibility, and total commitment to change. 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!"

    58 min

  2. DEC 4

    From Prison to Popcorn: Emily O’Brien’s Comeback Snacks Story

    What happens when your worst fear becomes your reality… and somehow becomes the launchpad for a popcorn empire? In this powerful episode of Nightmare Success In and Out, Brent Cassity sits down with Emily O’Brien, founder of Comeback Snacks, to unpack how a honors grad from Canada went from international development and corporate sales… to being groomed by a boyfriend, caught smuggling cocaine back from St. Lucia, and sentenced to four years in a Canadian prison. Emily shares the raw details of how quickly life can spin out of control, what it was like to be arrested at the airport, face her family in shackles, and navigate the Canadian prison system. She opens up about addiction, bad decisions, shame, and the brutal uncertainty of house arrest and sentencing. But this isn’t just a story about a fall — it’s about a comeback. Inside prison, Emily started experimenting with popcorn recipes, listening to other women’s stories, and dreaming up a brand that would stand for second chances. That prison-born idea became Comeback Snacks — a popcorn company that now sells in over 1,200 retail stores, hires formerly incarcerated people, and uses bold flavors to spark conversations about redemption and prison reform. From building a business out of a halfway house kitchen to speaking on stages, producing documentaries, and becoming a voice for fair-chance hiring, Emily proves that mistakes are universal — and so are comebacks. If you’ve ever wondered whether your worst decisions have to define you, this episode will hit home. Listen in as Brent and Emily talk prison, purpose, entrepreneurship, Comeback Snacks, and what it really takes to rebuild your life after a conviction. 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!"

    57 min

  3. NOV 20

    Why Not?”—Rusty Pangburn on Redemption, Radical Weight Loss & a Second-Chance Career

    What happens when your worst fear becomes your reality—and you decide to ask, “Why not?” instead of “Why me?” In this episode of Nightmare Success In and Out, host Brent Cassity sits down with Rusty (Rustin D.) Pangburn—author of Mindset Matters, founder of Why Not Mindset, motivational speaker, and CDL truck driver—to unpack a remarkable second-chance story. Rusty went from running the streets to serving a 60-month federal sentence, from 480+ lbs to 189 lbs, and from “inmate number” to mentor, author, and nonprofit leader helping justice-impacted people reenter with confidence. We dig into: The “Why Not” question that rewired Rusty’s life and inspired his book & nonprofit How he used walking, running, and routine to lose 300+ lbs inside RDAP, mindset shifts, and preparing for life after the gate Finding a career path in trucking (CDL) and building a future with his wife as team drivers Writing Mindset Matters and the “Ripple Effect” chapter—why small actions change lives Creating an AI-produced song to capture his story and mission If you’re looking for hope, practical reentry insight, and proof that mindset matters, this one’s for you. 📘 Rusty’s book: Mindset Matters🌐 Nonprofit: WhyNotMindset.net🎙️ Subscribe for weekly comeback stories & share with someone who needs a second chance. 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

  4. NOV 13

    Zero Excuses: Kristin Kline’s Convicted Comeback

    Coach Kristin Kline (“Zero Excuses”) turned a prison-yard workout into Convicted Comeback—a movement rebuilding women through fitness, mindset, and real credentials. Brent Cassity interviews Kristin Kline on the Nightmare Success In and Out Podcast. She opens up about childhood trauma, addiction, an armed-robbery charge, and the counselor who told her, “You’re not a gangster,” sparking a total reset. We get into how mindset is a muscle, the 60-day bootcamps that started on the yard, printing certificates inside, navigating reentry fear, and partnering with ISSA so people inside can earn trainer certifications that matter on the outside. Raw, hopeful, and packed with action for anyone fighting for a second chance. 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!"

    54 min

  5. NOV 6

    The Feds Couldn't Break Her Spirit: The Freya Pearson Story

    What happens when you refuse to take a plea deal and the full weight of the federal system lands on you?In this explosive episode, Brent Cassity talks with Freya Pearson, whose story takes you from the world of real estate and a lottery client… to a shocking trial, 60-month sentence, and a prison system full of corruption and retaliation. Freya opens up about: Being indicted and going to trial against federal prosecutors Corruption in the justice system and failures of defense Surviving Alderson and Aliceville federal prisons Writing up staff, exposing abuse, and surviving whatever came her way Coming home to rebuild her life as a paralegal and future attorney This is a raw, unfiltered story of resilience, accountability, and the power of standing up for yourself when everyone tells you to give up. 👉 Subscribe for more real comeback stories of hope 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 33m

  6. OCT 30

    Wrongfully Convicted at 17 to Innocence Pardon: Dieter Tejada’s Comeback | Nightmare Success In and Out

    At 17, a high-school party turned into a baseball-bat attack—and a life-altering case. Dieter Tejada took a plea to avoid a decade in prison, served time, then rebuilt everything: UConn, Vanderbilt Law, passing the bar—only to discover withheld exculpatory evidence years later. In September 2023, he received a full, unconditional pardon recognizing his innocence.Host Brent Cassity and Dieter dig into why innocent people plead guilty, reentry with an ankle monitor, confronting stigma, and the long road to an innocence-based pardon. Highlights The night everything changed (self-defense vs. narrative) Pressure to plead and how the system incentivizes it Reentry: college classes, ankle monitor, and resilience Finding 20+ missing pages in the police report From wrongful conviction to innocence pardon—and what changes now If this story moves you, follow, rate, and share to amplify real 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 29m

  7. OCT 23

    "Unshackled: Topeka Sam on Transforming Incarceration into Advocacy"

    Brent Cassity interviews Topeka Sam on the Nightmare Success Podcast, a true impact leader with an inspiring comeback story. Topeka K. Sam is a nationally recognized leader in criminal justice reform, dedicated to transforming the lives of women and girls impacted by incarceration. After serving time in federal prison herself, Topeka emerged as a powerful voice for change. She is the founder and Executive Director of The Ladies of Hope Ministries (The LOHM), an organization that provides housing, reentry support, and advocacy for formerly incarcerated women. Her story and mission have been featured by major outlets including The Today Show, CNN, The Tamron Hall Show, and The New York Times. Topeka has advised policymakers, including speaking at the White House and testifying before Congress, to advance legislation on prison reform and second chances. Topeka received a Presidential Pardon by President Trump on December 23, 2020. Passionate, fearless, and inspiring, Topeka Sam represents resilience and purpose-driven leadership. Through her advocacy, she challenges the stigma of incarceration and builds pathways of hope, dignity, and opportunity for women returning home. Topeka also does film work highlighting people who need to be released from prison. One of these films featured Alice Johnson that caught the attention of Kim Kardashian. Kim and Topeka teamed up and got President Trump to Pardon Ms. Johnson. Alice Johnson now serves as the Pardon Czar in the Trump Administration. 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 9m

  8. OCT 16

    “Behind the FTX Collapse: A Father’s Story of Survival”: Joe Bankman

    What happens when your son builds one of the largest crypto empires in history—and then it all comes crashing down? On this episode of Nightmare Success In and Out, Brent Cassity sits down with Joe Bankman, Stanford law professor and father of Sam Bankman-Fried, the convicted founder of FTX. In a candid and emotional conversation, Joe shares what it was like to watch the meteoric rise of FTX, the devastating collapse, and the personal toll it has taken on his family. This is not just a story about crypto or courtroom drama—it’s about fatherhood, resilience, and what it means to survive when your worst nightmare becomes your reality. Joe opens up about the weight of public scrutiny, the heartbreak of watching his son fall, and how he and his family are finding a path forward in the shadow of a global scandal. If you’ve ever wondered how families endure when the spotlight turns harsh, this episode is one you won’t forget. 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!"

    52 min
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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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