Brent Cassity: Author and Host of the Nightmare Success Podcast

We were honored to host Brent Cassity, author, speaker, and host of the podcast Nightmare Success In and Out, as our March 2024 White Collar Support Group Tuesday Night Speaker Series presenter. Brent joined us from his own podcast studio and gave us the whole arc, from the best year his family company ever had through five years at Leavenworth, and the five rules that got him through it. You can watch the full recording above.

Most of us tell our story as something that happened to us. Brent tells his as a room he walked out of and never went back to. If you are running something today and there is a corner of it you have decided belongs to somebody else, this hour is uncomfortable in the useful way. If you already have a report date, the middle of it is what our members bring up months later.

The $13 million he asked about once and never followed up

A friend who ran one of the country’s largest private insurers once told Brent over drinks why he had passed on buying a book of business from them. Too many policy loans. So Brent walked into his CFO’s office and asked what it would take to wipe out the $13 million on their books. About a hundred million dollars in sales, he was told. He ran the number, decided he could sell that much, and left the room. He never went back to see whether it happened.

The other thing is that I think about too, is when I look back and reflect on why didn’t I ask and do more when I was at the top of the food chain? And I think what the real answer is, is that I didn’t want to mess things up. My life was so good.

That is the honest version, and it is what makes this talk land. There is no moment in it where he decides to break a law, only a moment where he decides not to make things messy. The loans grew. A reinsurance fight his father refused to settle drained the companies into receivership, and a six-year investigation followed, six years of other people reading books that a financial expert of his own could have read first. The count that finally stuck was a 1994 statute almost nobody outside insurance has heard of, and it carried five years by itself. Money laundering, mail fraud and wire fraud stacked on top. He does that arithmetic out loud in the talk, and anyone staring at a number like that on their own case should follow it with Doug Passon on what actually decides a federal sentence months before the hearing.

What the night before a guilty plea actually looks like

Six years of fighting had become a routine, and the routine kept him from ever sitting down with what was coming. He was going to prison. He was going to be a felon. It landed on him the night before he pleaded, alone in the house, his wife and daughters up at the vacation home because he did not want them near him for it. He drank. He wrote out everything Julie had done for the family and all the fatherly advice he could think of for his girls. Then he took the keys and went out to the garage.

What stopped him is his to tell, and he tells it without flinching, the way Brian Cuban told our group about the .45 on his own nightstand. The part worth flagging is the sequence, because it is the most useful thing in the hour for anyone with a date on the calendar. He hit bottom before the gate, not inside it. By the time he and Julie drove out the next night to watch the lights come on along the fence at Leavenworth, who he would be in there was already settled. Members who have worked with Sam Mangel and Craig Rothfeld know the logistics of getting ready. This is the other half, and nobody puts it on a checklist.

The five rules he used to survive prison

His first night in A2, Brent climbed out of the bunk, carried a piece of paper over to the light from the bathroom, and wrote down what he meant to accomplish in there. Five rules came out of the five years that followed. He gives all of them in the talk. We will give away one, the one our members steal.

He kept a calendar his youngest daughter made him, and every night he wrote his win for the day in that day’s box. Forklift certified. A good phone call home. More push-ups than yesterday. Bad days went in the box too, felt all the way down.

My hack, I would never allow myself to fill in two boxes of bad side by side.

Two bad boxes become a bad week, then a bad month, then a man who is institutionalized. The other four run from humbling yourself enough to walk up to the men who are getting it right, which he calls getting “the answers to the test before the test,” to what he saw after release, in men more afraid of freedom than of prison and in the rest of us stuck in jobs and marriages we will not leave. He picked up a line for it: the ugly comfort routine becomes a warden to your freedom. Anyone building a new life after prison knows the circle he means.

About Brent Cassity

Brent Cassity is the author of Nightmare Success: Loyalty, Betrayal, Life Behind Bars, Adapting, And Finally Breaking Free, and the host of the podcast Nightmare Success In and Out, which many of our members have been guests on. He is building a nonprofit reentry company, Nightmare Success Solutions. Before all of it he was CEO of Forever Enterprises, the family company he grew from a regional operation into one working in 22 states and covered by TIME, CNN, Fortune, Forbes and the Wall Street Journal. He served five years at Leavenworth.