Nightmare Success In and Out

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

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

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

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

What happens after prison? For most people, that’s where the real struggle begins.
In this episode of Nightmare Success In and Out, Brent Cassity sits down with Doug Feller—an entrepreneur who went from building businesses and living fast… to facing federal charges, prison time, and starting over from nothing.
Doug shares the truth about reentry that nobody talks about:
👉 Why getting out of prison is just the beginning
👉 The stigma that follows you for life
👉 How he rebuilt from $10/hour jobs to building and selling a company
👉 Why he created the MyHarvest App to help others succeed after incarceration
“Getting out of prison isn’t the end of the sentence… it’s the beginning of the climb.”
This is more than a prison story—it’s a blueprint for resilience, second chances, and rebuilding your life when everything is gone.
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