Nightmare Success In and Out

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.comShow 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!"

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!"

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!"

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!"

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!"