Brent Cassity

Brent Cassity ran a national company. He was in TIME, Fortune, and the Wall Street Journal. HBO made a documentary about his business that later inspired "Six Feet Under." He had money, media attention, and a team across 22 states.

Then he went to prison.

How He Got There

Brent grew up in St. Louis. His family owned a funeral business. After graduating from the University of Missouri, he moved to Austin to build a sales team for National Prearranged Services, the family's pre-need funeral company. He broke sales records his first year and got promoted to run the entire Texas region.

By 1990, he was back in St. Louis running Cassity Heritage Funeral Homes. He looked at how funeral homes marketed themselves and thought it was stuck in the past. So he changed it. Video tributes. Better hospitality. Actual advertising. Things that seem obvious now but weren't common then.

The New York Times wrote about their revamped Hollywood Cemetery and called it "the cemetery of the 21st Century." Fortune did a profile. TIME covered them. HBO showed up with cameras. The documentary they made, "The Young and the Dead," got enough attention that it helped inspire the TV show "Six Feet Under."

What Went Wrong

In 2008, National Prearranged Services collapsed. The feds said customer money had been used for things it wasn't supposed to be used for. Over 97,000 people across 16 states were affected. The losses added up to more than $450 million.

In 2013, Brent pleaded guilty to fraud and money laundering charges. He got 60 months at Leavenworth.

Leavenworth is one of the oldest federal prisons in the country. Built in 1879. When you show up, you get processed through the main penitentiary. Big walls. Old stone. The kind of place that makes it very clear what you've lost.

Five Years Inside

Brent spent his sentence watching people. Some guys got crushed by prison. Others found ways to keep themselves together. A few actually got better.

He started figuring out what separated the people who survived from the ones who didn't. It came down to a handful of mental strategies. Ways of thinking that helped you adapt when everything around you was designed to break you down. He calls them his "5 Rules."

Those same rules work outside prison too. Divorce. Getting fired. Addiction. Health problems. Any situation where you feel trapped and can't see a way forward.

After

When Brent got out, he didn't try to pretend it never happened. He wrote a book about it: Nightmare Success. The whole story. What led up to it, what prison was actually like, and how he put himself back together after. It became an Amazon bestseller.

Then he started this podcast. Over 200 episodes now. Every week he talks to someone who went through something similar. Wrongful convictions. White collar cases. Addiction. Athletes who lost everything. Entrepreneurs who crashed and rebuilt.

The conversations get real. These aren't polished PR interviews. People talk about what they actually did, what it cost them, and how they found their way back.

Some Guests You'll Hear

• Ameer Williams — Grew up dealing drugs, did time, came out and became a police sergeant.
• Brandon James — Spent 10 years locked up, now runs a roofing company doing $60 million a year.
• Topeka Sam — Did federal time, became a national voice for criminal justice reform.
• Shaun Hayes — Small-town guy who sold a bank for $400 million, then ended up in prison.

The Name

"Nightmare Success" sounds like a contradiction. That's the point. Brent's worst fear came true. He went to federal prison. And somehow that became the foundation for what he does now.

He says everything you want is on the other side of fear. Easy to say. Harder to believe when you're standing at the gates of Leavenworth about to give up five years of your life.

But he did it. And so did the 200+ people he's interviewed on this show. Their stories prove that hitting bottom doesn't have to be the end.

"A lot of us build our own prisons. They're not made of concrete and razor wire, but they trap us just the same. The rules for getting out are the same either way."

Speaking

Brent does podcasts, keynotes, and panel discussions. He talks about:

• How to survive when everything falls apart
• What federal prison is actually like
• Building a business (and the mistakes that can destroy one)
• Second chances and why they matter