Nightmare Success In and Out

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.

Latest Episodes:

Mayor, Governor Candidate, Federal Inmate: Scott Maddox's Untold Story Jun 11, 2026

Show notes

Scott Maddox spent decades at the center of Florida politics.

He served as Mayor of Tallahassee, chaired the Florida Democratic Party, and ran statewide campaigns for Attorney General and Governor. He was widely viewed as one of Florida's rising political stars.

Then came the federal investigation, public scandal, conviction, and prison sentence that changed everything.

In this candid conversation, Scott joins Brent Cassity to discuss the pressures of politics, the realities of federal prosecution, surviving a public downfall, life inside federal prison, and the difficult road to rebuilding after losing power, reputation, and freedom.

This episode is ultimately about resilience, accountability, and discovering who you are when the titles, status, and influence are stripped away.

If you've ever faced failure, public criticism, or a life-changing setback, Scott's story offers a powerful perspective on surviving the fall and finding purpose on the other side.

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 at prisonist.org. Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount Visit Discoverability.co. Auto Plaza Direct "Your personal car concierge!" Let them handle every detail to find your perfect car autoplazadirect.com. Author Saffron Gustafson www.mynameissaffron.com, "My Name is Saffron." Author Nevin Shetty, "Second Chance Economics: How Hiring The Formerly Incarcerated Can Unlock $1 Trillion in GDP." www.secondchanceeconomics.com

From Homelessness to the Time 100 List | Desmond Meade's Incredible Redemption Story Jun 04, 2026

Show notes

In this powerful episode of Nightmare Success In and Out, host Brent Cassity sits down with Desmond Meade, one of the most influential voices in criminal justice reform and voting rights advocacy.

Before becoming a Time 100 Honoree, MacArthur Genius Grant recipient, Nobel Peace Prize Nominee, and national leader, Desmond was homeless, addicted, justice-impacted, and standing on railroad tracks contemplating ending his life with a train that never came.

Then everything changed.

Desmond shares his remarkable journey from prison and addiction to helping restore voting rights for more than 1.4 million Americans. He discusses overcoming despair, surviving incarceration, finding purpose through service, attending law school, and transforming personal pain into a movement that changed lives across the country.

This conversation is about redemption, resilience, second chances, faith, recovery, and discovering purpose after losing everything.

If you've ever felt defeated, hopeless, or written off by society, this episode will remind you that your story is not over.

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 at prisonist.org. Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount Visit Discoverability.co. Auto Plaza Direct "Your personal car concierge!" Let them handle every detail to find your perfect car autoplazadirect.com. Author Saffron Gustafson, "My Name is Saffron." Author Nevin Shetty, "Second Chance Economics: How Hiring The Formerly Incarcerated Can Unlock $1 Trillion in GDP." www.secondchanceeconomics.com

From Silence to Strength: Kalise White’s Justice-Impacted Comeback Story May 28, 2026

Show notes

On this episode of Nightmare Success In and Out, host Brent Cassity sits down with justice-impacted author Kalise White, whose powerful journey from trauma and silence to healing and purpose is inspiring people everywhere.

Kalise opens up about the pain, labels, and emotional battles she faced after her life changed forever—and how she rebuilt herself piece by piece instead of allowing her past to define her future.

Author of the books You Left Me, God Blessed Me and No Longer Silenced, Kalise shares raw truths about survival, identity, trauma, faith, and reclaiming your voice after everything falls apart.

This is a story about redemption, resilience, healing, and refusing to stay broken.

If you’ve ever faced shame, setbacks, judgment, incarceration, or the feeling that life knocked you down too hard… this episode is for 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 at prisonist.org. Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount Visit Discoverability.co. Auto Plaza Direct "Your personal car concierge!" Let them handle every detail to find your perfect car autoplazadirect.com. Author Saffron Gustafson, "My Name is Saffron." Author Nevin Shetty, "Second Chance Economics: How Hiring The Formerly Incarcerated Can Unlock $1 Trillion in GDP." www.secondchanceeconomics.com

The Golden Boy, Varsity Blues & Prison: Gordie Ernst’s Fall and Fight Back May 21, 2026

Show notes

What happens when the “golden boy” becomes national headlines overnight?

On this episode of Nightmare Success In and Out, host Brent Cassity sits down with former Georgetown University tennis coach Gordie Ernst for one of the most honest conversations yet about the infamous Varsity Blues Scandal.

Gordie opens up about growing up as Rhode Island’s “golden boy,” becoming a respected college coach, working with the Barack Obama family, and how his life exploded after the college admissions scandal became national news.

This is more than a story about indictment and prison. It’s about identity, shame, family, survival, rebuilding, and finding purpose after public failure.

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 at prisonist.org. Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount Visit Discoverability.co. Auto Plaza Direct "Your personal car concierge!" Let them handle every detail to find your perfect car autoplazadirect.com. Author Saffron Gustafson, "My Name is Saffron." Author Nevin Shetty, "Second Chance Economics: How Hiring The Formerly Incarcerated Can Unlock $1 Trillion in GDP." www.secondchanceeconomics.com

Pre-IPO Millions, Federal Conviction & Fighting Back | Michael Castillero on Nightmare Success May 14, 2026

Show notes

What happens when everything you built comes crashing down?

On this episode of Nightmare Success In and Out, host Brent Cassity sits down with Michael Castillero, co-founder of StraightPath Venture Partners, a pre-IPO investment firm that exploded into the world of private investing before becoming the target of a massive federal prosecution.

Michael shares his side of the story for the first time in depth — from immigrating from Panama and building a Wall Street career… to launching a booming pre-IPO investment company handling hundreds of millions of dollars… to being convicted in federal court and awaiting sentencing.

This is a raw conversation about:

Federal prosecution
Wall Street ambition
Asset seizures
Trial strategy
Family pressure
Public humiliation
Fighting the U.S. government
Redemption and survival

Michael discusses the rise of StraightPath Venture Partners, the government’s allegations, the emotional toll on his wife and children, and why he believes he was targeted and misunderstood.

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 at prisonist.org. Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount Visit Discoverability.co. Auto Plaza Direct "Your personal car concierge!" Let them handle every detail to find your perfect car autoplazadirect.com. Author Saffron Gustafson, "My Name is Saffron." Author Nevin Shetty, "Second Chance Economics: How Hiring The Formerly Incarcerated Can Unlock $1 Trillion in GDP." www.secondchanceeconomics.com

She Was a Credit Union President… Then the FBI Showed Up | Kelly Givens’ Story May 07, 2026

Show notes

What happens when a career built on trust… ends in a federal conviction?

In this episode of Nightmare Success In and Out, Brent sits down with Kelly Givens, a former credit union executive whose life changed overnight when accounting mistakes and a federal investigation led to a prison sentence.

Kelly shares her raw and honest journey—from rising through the ranks to becoming president of a credit union… to facing the FBI, navigating the justice system, and ultimately serving time in federal prison.

But this isn’t just a story about the fall.

It’s about survival, accountability, and rebuilding a life after everything changes. Today, Kelly is using her platform @convicted.andclimbing to help others facing prison, reentry, and the stigma of a conviction.

This episode dives deep into:

What really happens during a federal investigation
The emotional toll of waiting for sentencing
The reality of women’s federal prison
The hidden struggles of reentry
Why telling your story can be the key to freedom

If you’ve ever wondered what it’s like to lose everything—and rebuild—it starts here.

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 at prisonist.org. Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount Visit Discoverability.co. Auto Plaza Direct "Your personal car concierge!" Let them handle every detail to find your perfect car autoplazadirect.com. Author Saffron Gustafson, "My Name is Saffron." Author Nevin Shetty, "Second Chance Economics: How Hiring The Formerly Incarcerated Can Unlock $1 Trillion in GDP." www.secondchanceeconomics.com

He Built a $13 Billion Empire… Became a Fugitive | Steve Keller Story Apr 30, 2026

Show notes

What happens when innovation collides with power?

On this episode of Nightmare Success In and Out, Brent Cassity sits down with entrepreneur Steve Keller, a man who built a multi-billion-dollar empire by revolutionizing the life settlement industry—only to watch it all unravel. Author of the new book "Pay to Play."

From launching securitized life insurance bundles on Wall Street to controlling 65% of the global life settlement market, Keller was at the top. His company, Kelco, helped terminally ill patients access money when they needed it most.

But success brought attention… and enemies.

After disrupting the insurance industry, Keller found himself: Indicted by the federal government. Branded a fugitive. Sentenced to 14 years in federal prison.

This is a story of ambition, innovation, power, and survival—and what happens when the system turns against you.

📘 His new book Pay to Play dives even deeper into the truth behind it all.

👉 Don’t forget to LIKE, COMMENT, and SUBSCRIBE—it helps the show grow and reach more people.

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 at prisonist.org. Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount Visit Discoverability.co. Auto Plaza Direct "Your personal car concierge!" Let them handle every detail to find your perfect car autoplazadirect.com. Author Saffron Gustafson, "My Name is Saffron." Author Nevin Shetty, "Second Chance Economics: How Hiring The Formerly Incarcerated Can Unlock $1 Trillion in GDP." www.secondchanceeconomics.com

From Federal Prison to $78M Business: PJ Jensen on Addiction, Discipline & No-Excuses Recovery Apr 23, 2026

Show notes

What happens when addiction leads you to federal prison—but doesn’t break you?

In this episode of Nightmare Success In and Out, Brent Cassity talks with PJ Jensen, host of the LFG Life Podcast, about his journey through addiction, prison, and rebuilding his life with discipline and accountability.

PJ shares how prison changed his mindset, how he built a multi-million-dollar business after release, and the moment an intervention forced him to finally confront his addiction.

This is a powerful conversation about ownership, recovery, and what it really takes to create lasting 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 at prisonist.org. Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount Visit Discoverability.co. Auto Plaza Direct "Your personal car concierge!" Let them handle every detail to find your perfect car autoplazadirect.com. Author Saffron Gustafson, "My Name is Saffron." Author Nevin Shetty, "Second Chance Economics: How Hiring The Formerly Incarcerated Can Unlock $1 Trillion in GDP." www.secondchanceeconomics.com

Ambition Addiction: When Success Becomes Your Downfall | Juliet Jacobs Apr 16, 2026

Show notes

What happens when ambition—something we’re taught to chase our entire lives—becomes the very thing that leads to our downfall?

In this powerful episode of Nightmare Success In and Out, Brent Cassity sits down with Juliet Jacobs, author of Ambition Addiction, a justice-impacted survivor, and a mental health professional with over 30 years of experience.

Juliet shares her deeply personal journey—from a childhood rooted in high expectations and success-driven culture… to building a career helping others… to ultimately crossing a line that led to federal prison.

Together, they unpack the hidden dangers of ambition when it becomes compulsive, the emotional roots behind addiction, and how even the most driven individuals can lose themselves in the pursuit of success.

This episode dives into:

The difference between healthy ambition and addiction
How cultural and family expectations shape identity
The psychology behind overachievement and control
What happens when your moral compass starts to shift
Life inside prison and the journey of rebuilding after release

Juliet’s story is raw, honest, and deeply relatable—not just for those impacted by the justice system, but for anyone who has ever felt the pressure to succeed at all costs.

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 at prisonist.org. Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount Visit Discoverability.co. Auto Plaza Direct "Your personal car concierge!" Let them handle every detail to find your perfect car autoplazadirect.com. Author Saffron Gustafson, "My Name is Saffron." Author Nevin Shetty, "Second Chance Economics: How Hiring The Formerly Incarcerated Can Unlock $1 Trillion in GDP." www.secondchanceeconomics.com

Doctor Turned Defendant: The COVID Hero Who Took on the Government | Dr. Ron Elfenbein Story Apr 09, 2026

Show notes

What happens when your worst fear becomes your reality? On this episode of Nightmare Success In and Out, Brent Cassity sits down with Dr. Ron Elfenbein — a board-certified emergency room physician trained at Johns Hopkins who stepped up when the world shut down. During the COVID-19 pandemic, Ron didn’t wait. He acted. He built testing sites before most believed the virus would spread. He treated thousands of patients. He donated critical supplies across multiple states. He became a trusted voice on the frontlines when fear and uncertainty were everywhere. Then, without warning… everything changed. Federal charges. A criminal trial. His reputation, career, and freedom all on the line. But just when it looked like his nightmare was over, a federal judge issued a stunning decision — wiping away the conviction in a rare and powerful ruling 93 page opinion. And still… the fight isn’t over. The DOJ won an appeal overturning the the Chief Judge's acquittal. This is a story about courage under pressure, standing up for what you believe is right, and navigating a system that can turn on you overnight. It’s about resilience. It’s about truth. And it’s about what it really takes to survive — and keep fighting — when your nightmare isn’t finished yet 🎙️ Don’t forget to follow, subscribe, and share — it helps us bring more powerful stories like this to people who need them.

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 at prisonist.org. Protect your online reputation with Discoverability! Use code NIGHTMARE SUCCESS for an exclusive discount Visit Discoverability.co. Auto Plaza Direct "Your personal car concierge!" Let them handle every detail to find your perfect car autoplazadirect.com. Author Saffron Gustafson, "My Name is Saffron." Author Nevin Shetty, "Second Chance Economics: How Hiring The Formerly Incarcerated Can Unlock $1 Trillion in GDP." www.secondchanceeconomics.com

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