Writing Men In Prison For Their Psychological Tactics
A few years back, I decided to write a letter to Kevin Trudeau. If you’re not familiar with this master of gimmicks, he’s the guy behind countless books you’ve probably seen collecting dust at Goodwill, like Natural Cures “They” Don’t Want You to Know About. Trudeau was the quintessential pitchman of the 90s and 2000s, selling everything from health “cures” to financial advice in a way that made you believe he had all the insider secrets the world was hiding from you. He even hosted syndicated radio shows back when podcasts weren’t a thing, crafting a persona that was part conspiracy theorist, part self-help guru, and entirely captivating to a certain audience.
But Trudeau’s house of cards didn’t stay upright forever. The Federal Trade Commission (FTC) came after him hard, not just for making millions, but for the way he made them. His health claims were repeatedly found to be deceptive, like promoting natural remedies that supposedly cured everything from cancer to diabetes — claims that had no scientific backing. The FTC hit him with fines, which he often ignored or circumvented.
Eventually, the real nail in the coffin was his promotion of The Weight Loss Cure “They” Don’t Want You to Know About.In his infomercials, he claimed the book contained a surefire way to shed pounds effortlessly. The reality? The “cure” involved an extreme diet, daily injections of a prescription drug, and was far from effortless. When the FTC took him to court over misleading advertising, Trudeau refused to back down, leading to a $37.6 million fine.
But that wasn’t all. Kevin Trudeau’s troubles with the law extended beyond false advertising. He was also accused of living lavishly while claiming he couldn’t pay his fines, hiding assets, and failing to report income. In 2013, a federal judge had enough and sentenced him to 10 years in prison for contempt of court, marking the end of his reign as one of America’s most infamous modern-day hucksters.
While some see him as a snake oil salesman, others still admire his audacity and ability to tap into the fears and desires of millions. Either way, I decided to write him a letter.
At that time he was impisioned in Alabama I believe correctly, this was back in 2017ish. And I write the guy, you know, not thinking he was going to write me back.
So I’ve got to hand it to him. I mean, seriously — credit where it’s due. I go, “Damn, Kevin, you might just be one of the best hypnotists on the planet.” The guy had the entire world convinced that injecting pregnant women’s urine was the ultimate secret to staying thin. Let that sink in. Pregnant. Women’s. Urine. And people bought it — literally and figuratively.
What’s even crazier is how many products and spinoffs exploded because of his wild claims. The dude didn’t just sell a product; he sold a belief, a movement, a conspiracy-laden fantasy that had people scrambling for his next big “secret.” Whether you think he was a genius or a total scam artist, there’s no denying he knew how to get into people’s heads and make them see dollar signs where there were none. Hypnosis at its finest.
So he writes me back. It takes about a month. The letter starts:
“Dear Kali, thank you for the note. I understand you want to talk about advertising. At this time, all of my notes have to go to my assistant.”
And I’m sitting there thinking, Really? An assistant? Come on, Kevin, we both know you’re in federal prison. Who is this “assistant”? The guy pissed off everyone who ever worked with him and lost all his money. It’s not like someone’s sitting around in a suit, waiting to field his notes.
So I write him again. This time, I cut the fluff:
“Dear Kevin, cut the crap. You don’t have an assistant. Here’s $20 for commissary. Let’s talk ad copy.”
He writes back:
“Thanks for the $20. What specifically do you want to talk about with ad copy?”
And thus begins a back-and-forth that spans four months. Over the course of our exchange, he breaks down how he made $37 million using psychological tactics to sell, well, whatever he could. Say what you will about the man, but he’s an encyclopedia of persuasion techniques.
The sad thing is, Kevin eventually gets out of prison, serves his time, and jumps right back into his old hustle. It’s like watching a drug addict relapse or a man who left prison thinking the war is still going on. He’s still pitching the same recycled nonsense — “They don’t want you to know this!” — but his audience has dwindled. His shtick is old, and now everyone’s just watching to see how he reframes it this time. “Yes, I was in prison, but only because I was giving you the secrets they didn’t want you to know!” It’s predictable, almost tragic.
It reminds me of this woman I heard about who went to federal prison for running an illegal brothel. She wasn’t operating in the right jurisdiction, got caught, and did her time. When she got out — in her 60s, mind you — she went right back to prostituting. It was all she knew. She didn’t have a backup plan, just muscle memory for the only trade she’d ever mastered.
What really makes me curious, though, is why people go back to the very thing that caused their downfall. Is it the money? The familiarity? Or is it that, deep down, they can’t imagine doing anything else? It’s a strange kind of loyalty — to a career, a lifestyle, or maybe even a self-identity — that keeps pulling them back, no matter the cost.
