How Brent Cassity Gives Voice to an Invisible Community

Earlier this year, Stanford Law professor Joe Bankman sat down for a rare public conversation about the implosion of his son’s crypto empire. But this time, it was not with Anderson Cooper or a New York Times reporter, but with Brent Cassity – a former CEO who spent five years in federal prison for his role in one of Missouri’s largest corporate fraud cases.

The interview happened at the White Collar Conference 2025, a virtual gathering of people who’ve been prosecuted for financial crimes, their families, and the lawyers who work with them.

CNN’s Jeffrey Toobin delivered the keynote. Paul Weiss – one of the country’s most prestigious and controversial law firms – was the lead sponsor. And Cassity, a former federal offender with a podcast called Nightmare Success, was the one asking Bankman about what it’s like to watch your son become the face of a $10 billion collapse.

If that sounds like three parallel universes colliding on a Zoom call, that’s because it is. And that collision is the whole point.

The Mizzou kid who ended up at the gates of Leavenworth

Before any of this, Brent Cassity was a college student at the University of Missouri in Columbia, studying political science and government. After graduation, he returned to St. Louis and joined his father’s funeral services business, a company that was, by then, becoming something much bigger than a local operation.

A good move by Cassity, especially as the small family enterprise started growing into something sprawling: National Prearranged Services, Inc. sold contracts to customers who wanted to lock in the cost of their funerals in advance. The pitch was simple and appealing, especially to older customers on fixed incomes. Pay now, and your family won’t have to worry later.

Brent rose through the ranks. By his thirties, he was Director and Chairman of Lincoln Memorial Life Insurance Company, the entity that was supposed to hold the money safe. He also held titles at Forever Enterprises, National Heritage Enterprises, and other pieces of the corporate puzzle. The whole thing was run by his father, James Douglas “Doug” Cassity, and for years, the machine looked like it was working.

The company expanded across ten states.

The family lived well.

And then the machine collapsed.

A Ponzi scheme in funeral clothes

Federal prosecutors called it what it was: a Ponzi-like scheme that ran from 1992 to 2008. The money customers paid for their future funerals wasn’t being held in trusts or insurance policies, as state law required. Instead, prosecutors say, the funds were being siphoned off for unauthorized purposes and personal enrichment.

By the time it all unraveled, more than 97,000 customers had been victimized and the losses exceeded $450 million.

Families who thought they’d taken care of their final expenses were left scrambling. Some paid twice. Others never got the services they’d been promised.

On November 22, 2010, Brent Cassity was indicted alongside his father and four other defendants. On July 3, 2013, he pleaded guilty to wire fraud, mail fraud, and money laundering. Judge Jean C. Hamilton sentenced him to 60 months in federal prison at a minimum-security camp called Leavenworth.

His father got nearly ten years. The combined sentences for all six defendants totaled 36 years. The restitution order: $435 million.

Brent served his time and walked out the other side. The question, as it always is with these stories, was what happens next.

The podcast nobody expected

If you’ve spent any time around the reentry space – the ecosystem of nonprofits, consultants, and advocates working to help people rebuild after incarceration – you know the playbook: get a job that doesn’t require a background check, keep your head down, and try not to talk about it.

Cassity did the complete opposite.

In 2021, he launched Nightmare Success In and Out, a podcast built around conversations with people who’ve been through the justice system. Long, unvarnished conversations with former inmates he knew from Leavenworth and beyond, casting a net where he’d bring in any people willing to talk about what life looked like before, during, and after.

The title is a riff on his own trajectory: the nightmare of losing everything, and the strange success of coming out the other side with something to say.

As of late 2025, it has over 200 episodes and a devoted audience of people navigating their own legal trouble, family members trying to understand what their loved ones went through, and the occasional curious outsider wondering what this corner of the internet even looks like.

The format is old-school: two people talking, no gimmicks. But the guests are not. Former attorneys, startup founders, executives, and occasionally people with no profile at all, just a story about surviving the system and trying to figure out what comes after.

The invisible community

Here’s the thing about white-collar crime: because of the many failures of our criminal justice system, this is a population of highly educated, professionally trained people who are completely isolated and left with few choices but to disappear.

That’s where the White Collar Support Group comes in. Founded in 2016 by Jeff Grant, the group runs free weekly meetings on Zoom. Over 1,600 people have participated, from more than 40 states and a handful of other countries.

Cassity has become one of the visible faces of that community. At both the 2024 and 2025 White Collar Conference, he served as keynote interviewer, conducting the kind of fireside chats that tech conferences pay six figures to produce, except the people “on stage” are convicted felons, their family members, and the occasional Theranos whistleblower.

The 2024 conference opened with Cassity interviewing David Israel, the CEO of GOOD PLANeT Foods, who rebuilt his career after his own legal troubles. The 2025 edition featured a conversation with Joe Bankman, a Stanford professor talking publicly about his son Sam Bankman-Fried, the crypto wunderkind turned federal inmate, to an audience of people who understood exactly what that kind of fall feels like. (The interviews are available to the public on YouTube.)

None of this erases what happened.

Victims of the NPS fraud are still out there. Some of them have built websites cataloging Cassity’s history and pushing back against his public reinvention. A civil jury awarded $491 million in damages – money that will almost certainly never be fully collected unless YouTube monetization really kicks into high-gear. These are people who paid twice for funerals, or whose loved ones were buried in chaos, have not forgotten.

Cassity doesn’t pretend otherwise. In interviews, he acknowledges the conviction, the guilty plea, the harm. He talks about the experience of walking into Leavenworth and realizing that the life he’d built was gone. He’s written a memoir about it – Nightmare Success, published in 2021 – and the book doesn’t try to spin him as an innocent bystander.

But the same skills that let someone rise through a family business, build a national company, and eventually get prosecuted for running it wrong are also the skills that let someone build a podcast, write a book, and become a spokesperson for an underserved community.

The charisma that got him into trouble is the same charisma that makes the podcast work.

Whether you find that inspiring or infuriating probably depends on where you’re standing.

Podcasting as community infrastructure

The deeper story here isn’t really about Cassity. It’s about what happens when a population that’s been invisible suddenly gets access to the same tools everyone else has.

Podcasts are cheap to make. Zoom calls are free. Social media doesn’t require a background check. The same infrastructure that let a thousand wellness influencers build audiences from their living rooms is now available to people whose LinkedIn profiles have a five-year gap they’d rather not explain.

It’s can be a messy and complicated and occasionally uncomfortable to watch. But it’s also real in a way that most criminal justice discourse isn’t. These are people who actually went through the system, talking to each other, building something, and occasionally landing interviews that mainstream outlets couldn’t get.

What comes next

Cassity still lives in the St. Louis area, not far from Clayton, where the fraud was once headquartered.

He runs the Nightmare Success podcast. He speaks at universities. He’s working on a nonprofit aimed at reentry support. The American Greed episode is still out there, and so are the DOJ press releases, and so is the memory of 97,000 people who trusted a company that betrayed them.

And every week, a group of people who’ve been through something similar open their podcast apps and continue to explore this process through the Nightmare Success podcast.

If you’re looking for a story about what happens when the internet gives voice to communities that used to be invisible – including ones you might not want to hear from – this is as good an example as any.

Brent Cassity is one version of that story.

There will be more.