WEBVTT

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Welcome back to the Deep Dive. Today we are tackling

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a subject that, I mean, it feels almost synonymous

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with a certain era of American excess. Oh, absolutely.

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If I say the wolf, you immediately have an image

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in your head. Yeah. Leonardo DiCaprio. You're

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picturing Leonardo DiCaprio. You're picturing

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a white Lamborghini Countach. You're picturing,

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I don't know, lobsters being thrown at FBI agents

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on a yacht. You are thinking of the movie. Which

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is completely understandable. I mean, that Scorsese

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film was a massive cultural phenomenon. It really

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did. It turned a financial criminal into a kind

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of rock star. Exactly. And that is precisely

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why we're here today. We are going to push that

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Hollywood glamour aside. We have to. We are stripping

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away the cinematic lens to look at the actual

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source material regarding Jordan Belfort. And

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we have a massive stack of notes here, comprehensive

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biographical accounts, actual court documents

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regarding restitution, reports on his post -prison

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ventures and, you know, the nitty gritty mechanics

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of how his schemes actually work. The mission

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here is really specific, I think. We aren't here

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to retell the party stories. We want to understand

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the mechanics. Right. How does a dental school

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dropout become one of Wall Street's most notorious

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figures? And maybe more importantly, after losing

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absolutely everything, his freedom, his money,

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his family, how does he manage to sell himself

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back to the public? That is the big question.

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Yeah. Really is. Is this a genuine redemption

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arc or is it just the ultimate sales pitch? We're

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going to trace the rise, the reality of the fall,

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and the specific details of the restitution and

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reinvention that often get overlooked. Because

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when you actually look at the documents, the

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story is much more complex and frankly a lot

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more cynical than the movie suggests. And we

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have to start by just acknowledging the source

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of our perception, right? Most of what people

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know comes from his memoirs, The Wolf of Wall

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Street and Catching the Wolf of Wall Street.

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So his version. His version, exactly. But as

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we go through this, we have to weigh his narrative

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against the legal reality. The source material

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paints a picture of a man who is, above all else,

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a cyclical creature. He builds, he scales, he

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crashes, and then he pivots. So let's unpack

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this. Let's go right back to the beginning. Before

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the Ferraris, before the Quaaludes, we're talking

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about Jordan Ross Belfort, born 1962. Raised

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in Bayside, Queens. Right. And here is the first

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nugget from the file that I think just sets the

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stage perfectly. His parents, Max and Leah, were

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both accountants. Which is fascinating context,

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isn't it? I mean, think about that environment.

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Yeah. He grew up in a household where numbers

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were the language. You have this Jewish upbringing

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in Queens in the 60s and 70s, parents who understand

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the ledger, who understand profit and loss, liabilities

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and assets. You have to wonder how much of that

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financial literacy was just osmosis. He wasn't

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learning this from the street. He was probably

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learning it at the dinner table. And clearly,

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the entrepreneurial itch started early. I love

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this story from the source material, but I also

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want to scrutinize it a bit. So between high

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school and college, Belfort and a childhood friend,

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Elliot Lowenstern, they decide they're going

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to hustle. They head out to Jones Beach. A classic

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New York summer spot. A classic. And they aren't

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just hanging out. They are selling scooped Italian

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ice from styrofoam coolers. Now, the source says

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they made $20 ,000. In a single summer. Okay,

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let's just pause and do the math on that because

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that number sounds insane for a couple of teenagers.

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It does. We are talking about the early 1980s.

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Adjusted for inflation, that $20 ,000 back then

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is roughly equivalent to nearly $75 ,000 today.

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That is a staggering amount of cash for two kids

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on a beach. Right. I mean, when I was a teenager,

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a summer job meant making minimum wage bagging

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groceries. Yeah. Maybe you'll walk away with

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a couple grand if you're lucky. These two walked

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away with the equivalent of a mid -level corporate

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salary. How is that even physically possible?

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I know. Were they selling the ice for $50 a scoop?

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What was going on? It's a volume game, and it's

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a territory game. If we really analyze this,

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it's the first real sign of his sales DNA. It

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implies a few things. One, they weren't just

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selling a product. They were exploiting a captive

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market. Okay. You have hot people on a beach,

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dehydrated, looking for sugar. The demand is,

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you know, it's inelastic. Two, to move that much

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product, we're talking thousands and thousands

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of scoops, requires serious logistics. I hadn't

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even thought of that part. You have to keep the

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ice frozen in styrofoam coolers in the baking

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sun. You have to transport it. You have to hustle

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up and down the sand. It establishes that he

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wasn't afraid of the grind. Not at all. Carrying

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styrofoam coolers up and down Jones Beach isn't

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glamorous work. It's heavy. It's messy. But the

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margin was clearly there. Exactly. And it highlights

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his ability to spot a gap. It wasn't about the

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Italian ice itself. He didn't care about the

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culinary quality of it. No. It was about the

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arbitrage. Buy low, sell high, high volume. That

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is the blueprint for everything that comes later.

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So he has this pile of cash, this small fortune.

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For a kid his age. And he heads to American University,

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gets a degree in biology, believe it or not.

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Which is a surprise to a lot of people who just

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assume he studied finance or economics or something.

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Right. But then comes the pivot that changes

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everything. He takes that Italian ice money,

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and he enrolls in the University of Maryland

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School of Dentistry. He had a plan. He did. But

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this is where the story takes a really sharp

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left turn, and I want to get your take on whether

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this sounds like a true story or a wolf embellishment.

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Okay, let's hear it. It's day one at dental school.

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The dean gives the welcoming speech to the incoming

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class, and he says, and I'm quoting the source

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here, the golden age of dentistry is over. If

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you're here simply because you're looking to

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make a lot of money, you're in the wrong place.

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That is the legendary quote. Belford hears this

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and he drops out. Immediately. It's a very cinematic

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moment, isn't it? It feels almost too perfect.

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Yeah. I walked out the door right then and there.

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Do we buy that? Did it happen exactly like that?

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Well, you know, whether it happened that dramatically

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or whether it took him a week to process it,

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the outcome is the verified fact. True. He did

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drop out almost immediately. And I think even

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if he polished the anecdote for the book, the

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psychology behind it is real. How so? Most people

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go to dental school because they want to be dentists

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or they want the prestige or they have some desire

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to help people. For Belfort, the career was purely

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a vehicle. It was a vehicle for a financial outcome.

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Right. It was just a means to an end. Once the

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dean removed the promise of making a lot of money,

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the vehicle was useless to him. It's like buying

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a car to win a race and then finding out the

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car has no engine. You don't just sit in it.

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You get out. It crystallizes his motivation perfectly.

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It wasn't about the work. It was about the wealth.

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So dentistry is out. What does he do next? He

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goes into sales. Specifically, door -to -door

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meat and seafood on Long Island. This is the

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first legitimate adult business venture we see

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in the records. And again, look at the pattern.

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He creates a business called the Meat and Seafood

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Business. Not a very creative name. No, but descriptive.

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And he doesn't just sell a few steaks to housewives

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here and there. He scales it. He scales it aggressively.

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He claims he grew this business to employ several

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workers. They were moving 5 ,000 pounds of beef

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and fish a week. Let's just contextualize 5 ,000

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pounds. Please. That is two and a half tons of

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perishable product. Right. Weekly. In the 1980s,

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this isn't clicking a button on an app to order

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more inventory. No. This is physical inventory.

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You need trucks, you need freezers, you need

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drivers. And you need to sell it before it spoils.

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Precisely. It is a high -pressure logistical

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nightmare. And he's doing this door to door.

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But here's the foreshadowing. He scales it up,

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moving massive volume, and then it collapses.

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Poof. He falls for bankruptcy at age 25. Why

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do you think that happened? What went wrong?

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Well, looking at the retrospective analysis,

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it really suggests a focus on aggressive expansion

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sales, sales, sales without the underlying capital

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structure to support it. So selling faster than

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he could actually manage. Exactly. He was likely

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extending credit to customers or buying inventory

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on credit that he couldn't pay back fast enough.

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It establishes this boom and bust cycle, rapid

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scaling, followed by a total crash. And he was

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25 years old. and already bankrupt. That could

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have been the end of the story for a lot of people.

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It's a humiliating failure. You're back at square

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one. But for Belfour, it seems like it was just

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the warm -up. Uh -huh. So he's broke, he's 25,

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a family friend pulls some strings and gets him

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a trainee job at L .F. Rothschild, a real, you

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know, blue -blooded Wall Street firm. Finally,

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he is in the arena. But talk about bad timing.

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He gets there, he starts trading, he's ready

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to become a master of the universe, and then

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wham! Black Monday. The stock market crash of

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1987. Right. October 19, 1987. The biggest one

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-day percentage drop in stock market history.

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The Dow dropped 22 .6%. It was just chaos. It

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was. And L .F. Rothschild was hit hard. I mean,

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really hard. They started laying people off left

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and right. And Belfort. Being the low man on

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the totem pole was laid off almost immediately.

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So the universe is really testing him here. Dentistry?

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No. Meat business. Bankrupt. Wall Street. The

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market literally crashes the moment he arrives.

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But this is the crucial pivot point. This is

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where the wolf is actually born. How so? Because

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he can't play in the big leagues anymore. The

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big leagues are bleeding. L .F. Rothschild isn't

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hiring. Goldman isn't hiring. So he looks at

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the underbelly. He finds a job at a small brokerage

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center on Long Island selling penny stocks. And

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this leads to the founding of Stratton Oakmont.

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Now, originally, this was a franchise of something

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called Stratton Securities, right? It wasn't

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his name to start. Correct. He started as a franchisee,

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which is an interesting detail. He didn't invent

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the name immediately, but eventually he buys

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out the original founder and makes it his own.

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And this is where we need to explain what Stratton

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Oakmont actually was. Yes. Because in the movie,

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it just looks like a chaotic party where people

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are screaming into phones. But structurally,

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it was a boiler room. Let's break that down for

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the listener who might hear that term but not

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know the mechanics. What is a boiler room specifically?

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A boiler room is basically an outbound call center

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that sells questionable investments using high

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pressure sales tactics. They are literally turning

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up the heat on the investor. The term refers

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to the high pressure environment and often the

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physical location. Originally, these scams were

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run out of cheap basement offices, you know,

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near the boiler room of a building. And Stratton

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Oakmont specialized in marketing penny stocks.

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Right. Penny stocks are shares of very small

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public companies that trade at very low prices,

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usually under five dollars a share. They're highly

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volatile, thinly traded and very easy to manipulate

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because there isn't much public information about

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them. And the specific fraud they were running

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is. known as pump and dump i want to walk through

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this step by step so we understand exactly how

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the theft happened okay let's look at the mechanism

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described in the text it starts with the setup

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belfort and his partners stratton oakmont would

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acquire a huge position in a cheap stock sometimes

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they would control nearly the entire supply of

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the stock through what are called nominee accounts

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or rat holes rat holes that sounds pleasant It

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means they own the stock, but it's hidden in

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accounts under other people's names, so it doesn't

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look like Stratton Oakmont owns it all. Got it.

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That's step one. Step two is the pump. Belfort's

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army of brokers gets on the phones. And they

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had a very specific script for this, didn't they?

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I read about the Kodak pitch. This is the genius

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and the evil of the sales tactic. They wouldn't

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start by selling the garbage stock. They would

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call a potential client, often a blue -collar

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guy or a small business owner, and pitch a blue

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-chip stock. Something safe like Kodak or IBM

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or Disney. Mr. Smith, Kodak is poised for a breakout.

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Why do that? Why sell a legitimate stock first?

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To build trust. It's brilliant in a sinister

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way. If you buy Kodak and it goes up a few bucks,

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you think, hey, this broker knows his stuff.

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You trust him. You think he's on your side. Belfort

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called this papering the client. So once the

00:12:08.139 --> 00:12:10.700
client is papered and trusts the broker, then

00:12:10.700 --> 00:12:13.919
comes the switch. Exactly. Then comes the call

00:12:13.919 --> 00:12:16.840
for the house stock. the garbage penny stock

00:12:16.840 --> 00:12:19.840
that Stratton Oakmont secretly owns. The broker

00:12:19.840 --> 00:12:23.259
calls back breathless with excitement. Mr. Smith,

00:12:23.419 --> 00:12:26.019
I have something incredible. It's a small company.

00:12:26.080 --> 00:12:28.320
It's about to explode, but you have to move now.

00:12:28.500 --> 00:12:31.879
That urgency, the scarcity. It's classic psychological

00:12:31.879 --> 00:12:35.120
manipulation. The client, who now trusts the

00:12:35.120 --> 00:12:38.080
broker, dumps his savings into this penny stock.

00:12:38.360 --> 00:12:41.450
And that's the bump. The price of the stock skyrockets

00:12:41.450 --> 00:12:43.389
because of this artificial demand created by

00:12:43.389 --> 00:12:45.909
the call center. And then? Then comes the dump.

00:12:46.250 --> 00:12:49.029
Once the price hits a peak, Stratton Oakmont

00:12:49.029 --> 00:12:51.509
and Belfort personally sell off their hidden

00:12:51.509 --> 00:12:54.450
holdings. They dump millions of shares into the

00:12:54.450 --> 00:12:56.870
market. Which kills the price. It obliterates

00:12:56.870 --> 00:12:59.289
it. The supply floods the market. The price crashes

00:12:59.289 --> 00:13:01.909
to zero. Belfort walks away with millions in

00:13:01.909 --> 00:13:05.419
cash. The investors, Mr. Smith in Ohio, the retiree

00:13:05.419 --> 00:13:08.419
in Florida, are left holding stock that is literally

00:13:08.419 --> 00:13:10.679
worthless. They lose everything. It's a direct

00:13:10.679 --> 00:13:13.360
transfer of wealth from the gullible to the manipulator.

00:13:13.460 --> 00:13:16.399
Correct. And the scale of this was unbelievable.

00:13:17.019 --> 00:13:19.480
The source says at one point, Stratton Oakmont

00:13:19.480 --> 00:13:22.820
employed over one... thousand stockbrokers. A

00:13:22.820 --> 00:13:26.019
thousand brokers. Imagine the noise in that room.

00:13:26.100 --> 00:13:28.179
Imagine the energy required to keep a thousand

00:13:28.179 --> 00:13:30.860
people lying on the phone all day. And they were

00:13:30.860 --> 00:13:33.580
involved in stock issues totaling over a billion

00:13:33.580 --> 00:13:37.480
dollars. A billion with a B. Including, famously,

00:13:37.659 --> 00:13:40.259
the IPO for Steve Madden Footwear. That was their

00:13:40.259 --> 00:13:43.159
crown jewel. Steve Madden was a legitimate company.

00:13:43.200 --> 00:13:45.840
They actually made shoes. Taking them public

00:13:45.840 --> 00:13:48.139
gave Stratton Oakmont a veneer of credibility.

00:13:48.460 --> 00:13:51.559
Right. Look, we aren't just selling penny stocks.

00:13:51.740 --> 00:13:54.460
We took Steve Madden public. But even that IPO

00:13:54.460 --> 00:13:57.159
was manipulated behind the scenes to ensure Belfer

00:13:57.159 --> 00:13:59.480
and his cronies controlled the share price from

00:13:59.480 --> 00:14:01.720
the jump. Now we have to talk about the culture

00:14:01.720 --> 00:14:04.200
that fueled this. Because you can't have a thousand

00:14:04.200 --> 00:14:06.100
young men ripping people off all day without

00:14:06.100 --> 00:14:08.320
a certain atmosphere. Oh yeah. The source material

00:14:08.320 --> 00:14:10.620
describes a life of lavish parties and intensive

00:14:10.620 --> 00:14:14.299
use of recreational drugs. Specifically methaqualone.

00:14:14.779 --> 00:14:17.039
Qualudes. The source mentions his addiction to

00:14:17.039 --> 00:14:19.970
qualudes explicitly. And this is where the movie

00:14:19.970 --> 00:14:22.409
leans in heavily. But from an analytical perspective,

00:14:22.570 --> 00:14:25.389
we have to look at what that drug does. Qualudes

00:14:25.389 --> 00:14:28.350
are a sedative hypnotic. They lower inhibitions.

00:14:28.370 --> 00:14:30.809
They make you feel invincible. They numb the

00:14:30.809 --> 00:14:32.830
moral center. Is that a fair way to put it? In

00:14:32.830 --> 00:14:36.309
a way, yes. When you are operating a billion

00:14:36.309 --> 00:14:38.710
dollar fraud while addicted to heavy sedatives,

00:14:38.909 --> 00:14:41.690
your risk assessment is completely broken. Yeah.

00:14:42.090 --> 00:14:44.269
You stop worrying about the SEC. You stop worrying

00:14:44.269 --> 00:14:47.289
about the FBI. You feel like a god. That drug

00:14:47.289 --> 00:14:49.669
-fueled invincibility likely accelerated the

00:14:49.669 --> 00:14:52.169
fraud. It pushed them to be more brazen, more

00:14:52.169 --> 00:14:54.629
reckless. So you have this boiler room. You have

00:14:54.629 --> 00:14:56.350
a thousand brokers. You have drugs. You have

00:14:56.350 --> 00:14:59.110
money pouring in. But you also have eyes on you.

00:14:59.330 --> 00:15:02.370
The government isn't blind. The regulatory cat

00:15:02.370 --> 00:15:04.330
and mouse game had to begin. The source says

00:15:04.330 --> 00:15:06.570
Stratton Oakmont was under near constant scrutiny.

00:15:07.049 --> 00:15:09.870
from the NSD, which is now Fine RA, from 1989

00:15:09.870 --> 00:15:12.570
onward. That is almost the entire existence of

00:15:12.570 --> 00:15:14.629
the firm. It was. They were fighting regulators

00:15:14.629 --> 00:15:17.570
constantly. Belfort spent a fortune on lawyers

00:15:17.570 --> 00:15:20.610
to delay, to obfuscate, to pay fines and just

00:15:20.610 --> 00:15:23.450
keep going. But the wheels finally fell off in

00:15:23.450 --> 00:15:27.690
December 1996. The NASD expelled Stratton Oakmont.

00:15:27.850 --> 00:15:29.750
They effectively put the firm out of business.

00:15:30.029 --> 00:15:32.610
But the criminal charges took a bit longer. It

00:15:32.610 --> 00:15:35.490
wasn't until 1999 that Belfort was indicted for

00:15:35.490 --> 00:15:37.669
securities fraud and money laundering. And this

00:15:37.669 --> 00:15:40.250
leads to the next major pivot in his life. The

00:15:40.250 --> 00:15:42.909
pivot from wolf to rat, if you want to use the

00:15:42.909 --> 00:15:45.649
street terminology. Because in the movies, not

00:15:45.649 --> 00:15:47.769
just the Belfort movie, but crime movies in general,

00:15:47.909 --> 00:15:51.289
there's this code of silence. Omerta, you don't

00:15:51.289 --> 00:15:53.940
snitch. You do your time. That is not what happened

00:15:53.940 --> 00:15:55.879
here. Not at all. Not at all. The source material

00:15:55.879 --> 00:15:59.539
is very clear. Jordan Belfort became an FBI informant.

00:15:59.639 --> 00:16:01.679
He didn't just talk. He wore a wire. He wore

00:16:01.679 --> 00:16:04.519
a wire against his partners and associates. He

00:16:04.519 --> 00:16:06.799
gathered evidence. He testified against them.

00:16:07.019 --> 00:16:08.899
I just want to pause on the reality of that for

00:16:08.899 --> 00:16:12.279
a second. Wearing a wire isn't simple. You are

00:16:12.279 --> 00:16:15.399
walking into a room with your best friends, people

00:16:15.399 --> 00:16:18.320
you have partied with, done drugs with, committed

00:16:18.320 --> 00:16:21.639
crimes with. And you're actively recording them

00:16:21.639 --> 00:16:23.960
to send them to prison. It's a profound betrayal.

00:16:24.860 --> 00:16:28.320
But it's also, it's a rational calculation. Hell

00:16:28.320 --> 00:16:30.899
so. Belfort is a salesman. He deals in transactions.

00:16:31.220 --> 00:16:34.379
The deal on the table from the FBI was, you are

00:16:34.379 --> 00:16:37.320
looking at 20 or 30 years in prison. Yeah. Give

00:16:37.320 --> 00:16:39.399
us everyone else and we will give you a discount.

00:16:39.899 --> 00:16:42.379
And he took the deal. He did the math. He realized

00:16:42.379 --> 00:16:45.399
his friends were a depreciating asset, and his

00:16:45.399 --> 00:16:47.320
freedom was the only thing that mattered. He

00:16:47.320 --> 00:16:49.440
sold out his friends to buy his freedom. And

00:16:49.440 --> 00:16:51.700
the discount was significant. Let's look at the

00:16:51.700 --> 00:16:53.980
sentence. He was sentenced to four years. Which,

00:16:54.059 --> 00:16:56.620
for a fraud of this magnitude, investor losses

00:16:56.620 --> 00:16:59.820
estimated at $200 million is remarkably light.

00:16:59.980 --> 00:17:01.980
It's nothing. There are people serving longer

00:17:01.980 --> 00:17:04.140
sentences for selling small amounts of marijuana.

00:17:04.460 --> 00:17:06.420
But he didn't even serve the four years. No,

00:17:06.539 --> 00:17:10.630
he served 22 months. 22 months. He did less than

00:17:10.630 --> 00:17:14.289
two years for a $200 million fraud. At the Taft

00:17:14.289 --> 00:17:16.650
Correctional Institution in California. And let's

00:17:16.650 --> 00:17:19.089
be clear about Taft. This isn't Rikers Island.

00:17:19.390 --> 00:17:22.450
No, it's often referred to as club fed. It's

00:17:22.450 --> 00:17:24.690
a low security camp, no bars on the windows,

00:17:24.829 --> 00:17:28.210
dorm style living. But still, it is a loss of

00:17:28.210 --> 00:17:30.509
freedom. And this is where the story gets really

00:17:30.509 --> 00:17:33.250
weird. Because you think, okay, he's in prison,

00:17:33.349 --> 00:17:36.839
he's disgraced, the party is over. But even in

00:17:36.839 --> 00:17:40.160
prison, the universe throws him a lifeline. Or

00:17:40.160 --> 00:17:42.319
rather, a cellmate. This is one of those facts

00:17:42.319 --> 00:17:44.480
that if you wrote it in a screenplay, a producer

00:17:44.480 --> 00:17:46.500
would tell you to cut it because it's too unbelievable.

00:17:46.980 --> 00:17:50.000
Right. His cellmate was Tommy Chong. As in Cheech

00:17:50.000 --> 00:17:52.619
and Chong, the guy from Up in Smoke? The stoner

00:17:52.619 --> 00:17:55.819
comedy icon. Chong was in there for a paraphernalia

00:17:55.819 --> 00:17:58.099
charge -selling bongs online, essentially. Which

00:17:58.099 --> 00:18:00.160
was a huge controversy at the time. So you have

00:18:00.160 --> 00:18:02.000
the Wolf of Wall Street and Tommy Chong sharing

00:18:02.000 --> 00:18:04.380
a bunk in California. And they're swapping stories.

00:18:05.000 --> 00:18:07.700
I'd love to have been a fly on that wall. Exactly.

00:18:08.279 --> 00:18:10.700
Belfort is telling these wild tales about the

00:18:10.700 --> 00:18:13.000
midget tossing, the yacht sinking, the drugs,

00:18:13.119 --> 00:18:16.660
and Chong is just listening. And Chong is the

00:18:16.660 --> 00:18:18.380
one who says, hey, you should write this down.

00:18:18.759 --> 00:18:21.720
Chong told him, this is a book. You are a natural

00:18:21.720 --> 00:18:23.960
storyteller. You need to write your memoirs.

00:18:24.140 --> 00:18:26.619
Chong basically coached him into his next career.

00:18:26.880 --> 00:18:29.660
So Belfort starts writing. The source says he

00:18:29.660 --> 00:18:33.440
actually wrote and destroyed 130 pages at first,

00:18:33.539 --> 00:18:36.390
a false start. He tried to write it like a novel,

00:18:36.450 --> 00:18:39.970
and it was bad. But eventually, he finds his

00:18:39.970 --> 00:18:42.890
voice. He produces The Wolf of Wall Street and

00:18:42.890 --> 00:18:44.769
Catching the Wolf of Wall Street. And the commercial

00:18:44.769 --> 00:18:47.390
instinct kicks in again. These books were published

00:18:47.390 --> 00:18:50.789
in roughly 40 countries, translated into 18 languages.

00:18:51.109 --> 00:18:53.710
And here's the kicker. A bidding war for the

00:18:53.710 --> 00:18:56.549
film rights began before the first book was even

00:18:56.549 --> 00:18:58.490
released. He hadn't even published the book yet

00:18:58.490 --> 00:19:01.190
and Hollywood was already throwing money at him.

00:19:01.309 --> 00:19:03.450
Wow. It just shows the undeniable appeal of the

00:19:03.450 --> 00:19:06.309
story. Studios and new audiences would eat up

00:19:06.309 --> 00:19:08.710
this tale of debauchery. But we have to pause

00:19:08.710 --> 00:19:11.190
here and look at the fact versus fiction aspect.

00:19:11.990 --> 00:19:15.089
Because Belfort is the narrator of his own life.

00:19:15.809 --> 00:19:19.690
And he has a history of, let's call it, creative

00:19:19.690 --> 00:19:22.529
truth. He is a notoriously unreliable narrator.

00:19:22.809 --> 00:19:25.289
The former federal prosecutor who led the investigation

00:19:25.289 --> 00:19:28.309
is quoted in our source material. He said that

00:19:28.309 --> 00:19:31.490
Belfer invented much and aggrandized his importance.

00:19:31.710 --> 00:19:34.029
Aggrandized his importance? The man who calls

00:19:34.029 --> 00:19:36.440
himself the wolf. I'm shocked. Chuckles. Right.

00:19:37.039 --> 00:19:40.220
But the prosecutor's point is crucial. He emphasized

00:19:40.220 --> 00:19:42.480
that the real story isn't just the parties and

00:19:42.480 --> 00:19:45.119
the fun. It involves thousands of victims who

00:19:45.119 --> 00:19:47.579
lost their savings. Yeah. When we get swept up

00:19:47.579 --> 00:19:49.740
in the narrative of the wolf, we forget the sheep,

00:19:49.859 --> 00:19:52.079
the people who got slaughtered financially. The

00:19:52.079 --> 00:19:54.920
book makes it funny. The reality was tragic for

00:19:54.920 --> 00:19:57.240
the victims. That is a perfect segue into the

00:19:57.240 --> 00:19:59.440
money trail because part of his sentence wasn't

00:19:59.440 --> 00:20:01.940
just time. It was restitution. He was ordered

00:20:01.940 --> 00:20:05.819
to pay back $110 .4 million to his victims. victims.

00:20:05.839 --> 00:20:07.880
Correct. That was the legal debt. So let's look

00:20:07.880 --> 00:20:11.000
at the scorecard. As of 2013, which is years

00:20:11.000 --> 00:20:13.759
after his release, how much had the victims recovered?

00:20:14.059 --> 00:20:17.480
About $10 million. Out of $110 million. That

00:20:17.480 --> 00:20:19.960
is less than 10%. And most of that $10 million

00:20:19.960 --> 00:20:22.640
didn't come from Belfort writing checks. It came

00:20:22.640 --> 00:20:24.799
from the sale of forfeited properties, houses,

00:20:24.920 --> 00:20:28.559
cars that the government seized early on. It

00:20:28.559 --> 00:20:30.900
wasn't coming from his new income. This brings

00:20:30.900 --> 00:20:34.769
us to the 50 % dispute. This is a legal battle

00:20:34.769 --> 00:20:37.430
that really highlights how Belfort operates.

00:20:37.809 --> 00:20:40.089
I want to dive into the legalese here because

00:20:40.089 --> 00:20:42.809
it shows his mindset. It does. So his original

00:20:42.809 --> 00:20:45.509
sentencing agreement stated he had to pay 50

00:20:45.509 --> 00:20:48.730
% of his gross income toward restitution. That

00:20:48.730 --> 00:20:50.650
sounds like a lot, right? Half of everything

00:20:50.650 --> 00:20:52.769
you make goes to the victims. Right. If you make

00:20:52.769 --> 00:20:55.430
a million, the victims get $500 ,000. Seems fair.

00:20:55.750 --> 00:20:59.210
But in 2013, federal prosecutors filed a complaint

00:20:59.210 --> 00:21:02.029
saying he was in default. They claimed he wasn't

00:21:02.029 --> 00:21:05.470
paying. And Belford's lawyers had a very technical

00:21:05.470 --> 00:21:08.569
argument. A very technical argument. They argued

00:21:08.569 --> 00:21:11.210
that the 50 % requirement was only valid during

00:21:11.210 --> 00:21:13.890
his parole. Technically, it's called supervised

00:21:13.890 --> 00:21:17.250
release. His supervised release ended in 2009.

00:21:17.930 --> 00:21:21.250
Therefore, his lawyers argued, once that supervision

00:21:21.250 --> 00:21:24.269
period ended, the contractual obligation to pay

00:21:24.269 --> 00:21:29.319
50 % That is bold. I'm off parole, so I don't

00:21:29.319 --> 00:21:31.359
have to give you half my money anymore, even

00:21:31.359 --> 00:21:34.039
though I still owe $100 million. It's legalistic

00:21:34.039 --> 00:21:38.160
jujitsu. And the judge agreed, or at least ruled,

00:21:38.279 --> 00:21:41.480
that the specific 50 % requirement had expired.

00:21:42.170 --> 00:21:44.490
with the supervision, so they had to strike a

00:21:44.490 --> 00:21:46.670
new deal. What was the new deal? He has to pay

00:21:46.670 --> 00:21:50.369
a minimum of $10 ,000 per month for life. $10

00:21:50.369 --> 00:21:52.269
,000 a month. Now, for the average listener,

00:21:52.450 --> 00:21:55.009
$10 ,000 a month is a huge amount of money. Sure.

00:21:55.170 --> 00:21:57.450
But for a guy who claims to make millions in

00:21:57.450 --> 00:22:00.710
speaking fees, it's a drop in the bucket. Let's

00:22:00.710 --> 00:22:03.950
do the math. $10 ,000 a month is $120 ,000 a

00:22:03.950 --> 00:22:06.160
year. To pay off the remaining $100 million,

00:22:06.380 --> 00:22:10.599
it would take roughly 833 years. So the victims

00:22:10.599 --> 00:22:12.880
are never getting that money back. Mathematically,

00:22:13.000 --> 00:22:15.960
no. Unless he voluntarily writes a check for

00:22:15.960 --> 00:22:19.480
$100 million, the victims are out of luck. And

00:22:19.480 --> 00:22:21.420
there was also a controversy regarding the movie

00:22:21.420 --> 00:22:24.329
Royalties, right? I remember seeing him claim

00:22:24.329 --> 00:22:26.950
he was giving all the money to the victims. He

00:22:26.950 --> 00:22:30.049
went on TV and said it. He did claim that. On

00:22:30.049 --> 00:22:32.549
his website, on Facebook, in interviews, he said,

00:22:32.630 --> 00:22:35.250
I am not making a dime from the movie or the

00:22:35.250 --> 00:22:39.089
books. I am turning over 100 % of the royalties

00:22:39.089 --> 00:22:41.930
to the victims. That sounds noble. That sounds

00:22:41.930 --> 00:22:44.700
like redemption. It does. But the U .S. attorney

00:22:44.700 --> 00:22:47.599
stepped in and filed documents saying that claim

00:22:47.599 --> 00:22:51.819
was not factual. They pointed out that he had

00:22:51.819 --> 00:22:54.039
received money from the initial sale of the film

00:22:54.039 --> 00:22:56.920
rights and kept it. Businessweek had a report

00:22:56.920 --> 00:22:59.220
on this that was pretty damning. Yes. They reported

00:22:59.220 --> 00:23:01.200
that before the movie release, out of roughly

00:23:01.200 --> 00:23:04.819
$1 .2 million he received, he had paid only $21

00:23:04.819 --> 00:23:09.420
,000 toward restitution. $21 ,000 out of $1 .2

00:23:09.420 --> 00:23:12.289
million. That's not even 50%. That's not even

00:23:12.289 --> 00:23:15.609
2%. So there is a massive gap between the redemption

00:23:15.609 --> 00:23:17.710
brand, the guy who says I'm giving it all back,

00:23:17.930 --> 00:23:21.210
and the financial reality. He was keeping the

00:23:21.210 --> 00:23:23.829
vast majority of the cash while telling the public

00:23:23.829 --> 00:23:26.710
he was a martyr for his victims. That gap brings

00:23:26.710 --> 00:23:31.390
us to his current career. Reinvention. He didn't

00:23:31.390 --> 00:23:33.990
go hide in a hole. He didn't retire quietly.

00:23:34.599 --> 00:23:36.839
he pivoted to motivational speaking and sales

00:23:36.839 --> 00:23:39.579
training. He became a guru. And markets it as

00:23:39.579 --> 00:23:42.279
Jordan Belfort's straight -line sales psychology.

00:23:42.720 --> 00:23:45.000
Which is incredibly ironic if you think about

00:23:45.000 --> 00:23:47.859
it. He is teaching the straight -line system.

00:23:48.299 --> 00:23:51.140
Is that a new system? Did he invent this post

00:23:51.140 --> 00:23:54.200
-prison? No, that is the exact same sales technique

00:23:54.200 --> 00:23:57.309
he developed at Stratton Oakmont. It is the system

00:23:57.309 --> 00:24:00.630
he used to train those 1 ,000 brokers to defraud

00:24:00.630 --> 00:24:03.549
people. He has repackaged the weapon of the crime

00:24:03.549 --> 00:24:06.269
as a legitimate business tool. And people are

00:24:06.269 --> 00:24:08.750
paying for it. They're paying a lot. His speaking

00:24:08.750 --> 00:24:12.230
fees range from $30 ,000 to $75 ,000 per engagement.

00:24:12.430 --> 00:24:15.329
His sales seminars can cost $80 ,000 or more

00:24:15.329 --> 00:24:18.180
for corporate training. Who is paying that? Who

00:24:18.180 --> 00:24:20.339
hires a convicted fraudster to train their sales

00:24:20.339 --> 00:24:22.680
team? That is the fascinating market question.

00:24:22.880 --> 00:24:25.359
It's a mix. You have aspiring entrepreneurs who

00:24:25.359 --> 00:24:27.579
see his wealth and want the secret. You have

00:24:27.579 --> 00:24:29.539
legitimate companies who think, well, say what

00:24:29.539 --> 00:24:31.440
you want about his ethics. The guy knows how

00:24:31.440 --> 00:24:33.859
to close a deal. They want the technique without

00:24:33.859 --> 00:24:36.240
the jail time. They think they can strip mine

00:24:36.240 --> 00:24:39.160
the skill and leave the fraud behind. It's dangerous

00:24:39.160 --> 00:24:42.000
territory. It is. Because the technique itself,

00:24:42.200 --> 00:24:44.240
the high pressure, the psychological manipulation

00:24:44.240 --> 00:24:47.799
is inherently aggressive. And speaking of dangerous

00:24:47.799 --> 00:24:50.660
territory, the source mentions a scandal in Australia

00:24:50.660 --> 00:24:54.519
that sounds suspiciously familiar. This is something

00:24:54.519 --> 00:24:56.440
that often gets buried under the movie hype.

00:24:56.619 --> 00:24:59.359
This is a really important detail. The Australian

00:24:59.359 --> 00:25:01.900
training scandal. Tell me about this. What happened

00:25:01.900 --> 00:25:05.039
down under? An investigation by 7 News and the

00:25:05.039 --> 00:25:07.099
Sunday Mail in Australia found links between

00:25:07.099 --> 00:25:09.599
Belfort and a company called Face -to -Face Training

00:25:09.599 --> 00:25:12.440
and another called Career Pathways Australia.

00:25:13.279 --> 00:25:15.920
Belfort gave workshops for the staff of these

00:25:15.920 --> 00:25:18.420
companies. He was the brand ambassador. He promoted

00:25:18.420 --> 00:25:20.440
them heavily. And what was the business model

00:25:20.440 --> 00:25:22.339
of these companies? They were vocational training

00:25:22.339 --> 00:25:24.940
companies. In Australia, the government provides

00:25:24.940 --> 00:25:28.220
funding for worker training. Ah, government money.

00:25:28.339 --> 00:25:31.180
Yeah. Always a target. Right. So face to face

00:25:31.180 --> 00:25:33.799
training was receiving millions in state government

00:25:33.799 --> 00:25:37.000
funding to train employees. But the investigation

00:25:37.000 --> 00:25:40.619
alleged that the training never happened. A ghost

00:25:40.619 --> 00:25:43.400
training program. Nine News Australia called

00:25:43.400 --> 00:25:46.119
it a tick and flick scam. Tick and flick. What

00:25:46.119 --> 00:25:48.259
does that mean? You tick the box to say someone

00:25:48.259 --> 00:25:50.640
was trained. You flick the paperwork to the government

00:25:50.640 --> 00:25:53.500
and you collect the check. The employees never

00:25:53.500 --> 00:25:56.519
got the training. But the company got the funding.

00:25:56.740 --> 00:25:58.720
And Belfort was involved with them. He was the

00:25:58.720 --> 00:26:00.759
face of their workshops. He was training the

00:26:00.759 --> 00:26:02.920
people who are running this scheme. Now, to be

00:26:02.920 --> 00:26:05.240
fair, the source doesn't say Belfort was the

00:26:05.240 --> 00:26:07.660
architect or the owner of that specific scam.

00:26:07.880 --> 00:26:10.240
OK, so he wasn't charged with anything. No, he

00:26:10.240 --> 00:26:12.799
wasn't charged, but he was in the orbit of it.

00:26:12.960 --> 00:26:15.640
He was a paid associate of a company accused

00:26:15.640 --> 00:26:18.319
of a multimillion dollar fraud against the government.

00:26:18.559 --> 00:26:21.339
That pattern again. Exactly. He finds himself

00:26:21.339 --> 00:26:25.230
adjacent to or directly. involved in situations

00:26:25.230 --> 00:26:27.890
where value is being faked and money is being

00:26:27.890 --> 00:26:30.970
extracted from a large faceless entity. First,

00:26:31.049 --> 00:26:33.109
it was investors. Then it was the Australian

00:26:33.109 --> 00:26:35.309
government. It's like he has a magnet for it.

00:26:35.569 --> 00:26:38.529
Or maybe he is the magnet. It suggests that even

00:26:38.529 --> 00:26:41.430
in his legitimate phase, he attracts operators

00:26:41.430 --> 00:26:44.710
who cut corners. Precisely. Birds of a feather.

00:26:45.470 --> 00:26:48.809
Let's shift gears to his modern moves. Because

00:26:48.809 --> 00:26:51.700
a guy like Belfort. has to stay on the cutting

00:26:51.700 --> 00:26:54.500
edge of money. What is the cutting edge right

00:26:54.500 --> 00:26:58.859
now? Crypto, of course. Of course. And his journey

00:26:58.859 --> 00:27:01.640
with cryptocurrency is classic Belfort. A flip

00:27:01.640 --> 00:27:05.240
-flop. A total 180. Originally, back around 2017,

00:27:05.579 --> 00:27:08.279
he was a massive skeptic. He called Bitcoin freaking

00:27:08.279 --> 00:27:10.900
insanity and mass delusion. He was on TV telling

00:27:10.900 --> 00:27:13.099
people to get out before they lost everything.

00:27:13.319 --> 00:27:15.440
I remember that. He was warning people away from

00:27:15.440 --> 00:27:17.059
it. He sounded like the voice of reason for a

00:27:17.059 --> 00:27:20.500
minute. But then prices skyrocketed. The market

00:27:20.500 --> 00:27:23.799
cap hit trillions and suddenly the wolf changed

00:27:23.799 --> 00:27:27.079
his tune. Now he is an inventor in crypto startups.

00:27:27.259 --> 00:27:29.559
He has pivoted to being a crypto bull. Why the

00:27:29.559 --> 00:27:31.640
change? Did he suddenly understand the technology

00:27:31.640 --> 00:27:33.740
better? Cynically. I think he saw where the money

00:27:33.740 --> 00:27:37.559
was. Yeah. Belfort chases liquidity. When the

00:27:37.559 --> 00:27:39.829
money was in meat, he sold meat. When it was

00:27:39.829 --> 00:27:42.269
in penny stocks, he sold stocks. Now the money

00:27:42.269 --> 00:27:45.150
is in crypto, so he sells crypto wisdom. But

00:27:45.150 --> 00:27:48.250
the blockchain bit him back. It did. In 2021,

00:27:48.569 --> 00:27:52.029
a hacker stole $300 ,000 in digital tokens from

00:27:52.029 --> 00:27:54.970
his crypto wallet. There is a certain irony in

00:27:54.970 --> 00:27:57.009
the wolf getting robbed. There is. He was very

00:27:57.009 --> 00:27:59.589
vocal about it, very angry. But it shows that

00:27:59.589 --> 00:28:02.470
even the master can get played in this new Wild

00:28:02.470 --> 00:28:04.769
West. I also want to touch on the yacht incident.

00:28:04.970 --> 00:28:07.309
Yeah. Because the sinking of the Nadine is such

00:28:07.309 --> 00:28:11.630
a perfect metaphor for his hubris. The source

00:28:11.630 --> 00:28:13.650
gives us some specific details on this that are

00:28:13.650 --> 00:28:17.849
just wild. Yes. The yacht, the Nadine. And you

00:28:17.849 --> 00:28:19.910
know who it was originally built for? No. Poco

00:28:19.910 --> 00:28:22.150
Chanel. Get out. I did not know that. That's

00:28:22.150 --> 00:28:24.190
a piece of genuine history. It was a beautiful

00:28:24.190 --> 00:28:29.039
historic vessel and Jordan Belfort sank it. Ego.

00:28:29.200 --> 00:28:32.259
Pure ego. He insisted on sailing into high winds

00:28:32.259 --> 00:28:34.539
off the coast of Sardinia. The captain, the expert,

00:28:34.660 --> 00:28:36.359
the guy who actually knows how to sail, advised

00:28:36.359 --> 00:28:38.640
him against it, said it was dangerous, said the

00:28:38.640 --> 00:28:41.640
wingers were too high. And Belfort. Belfort overruled

00:28:41.640 --> 00:28:44.859
him. He essentially said, I'm the wolf. I control

00:28:44.859 --> 00:28:47.220
the weather. Full steam ahead. And nature didn't

00:28:47.220 --> 00:28:50.180
care about his ego. The waves smashed the foredeck

00:28:50.180 --> 00:28:53.619
hatch. The yacht took on water and sank. It's

00:28:53.619 --> 00:28:55.599
at the bottom of the Mediterranean. And everyone

00:28:55.599 --> 00:28:58.079
on board. They all had to be rescued by Italian

00:28:58.079 --> 00:29:00.519
Navy Special Forces. It's the Stratton Oakmont

00:29:00.519 --> 00:29:03.480
story in miniature. Ignore the rules. Ignore

00:29:03.480 --> 00:29:06.180
the experts. Push full throttle until the whole

00:29:06.180 --> 00:29:08.480
thing goes under. And assume someone will come

00:29:08.480 --> 00:29:12.000
rescue you. Which, in both cases, they sort of

00:29:12.000 --> 00:29:15.220
did. He survived the yacht sinking and he survived

00:29:15.220 --> 00:29:17.660
the prison sentence. He always seems to have

00:29:17.660 --> 00:29:20.730
a life raft. Let's touch... Briefly on his politics

00:29:20.730 --> 00:29:23.269
before we wrap up, because for a guy who lives

00:29:23.269 --> 00:29:25.970
such a chaotic life, his political views are

00:29:25.970 --> 00:29:29.490
interesting. They are a mix. In the 90s, he donated

00:29:29.490 --> 00:29:32.869
to the Republican Party $100 ,000. OK, straightforward

00:29:32.869 --> 00:29:35.970
enough. But socially, he describes himself as

00:29:35.970 --> 00:29:38.049
a liberal at heart. He's pro -choice, things

00:29:38.049 --> 00:29:40.589
like that. He's not a staunch conservative on

00:29:40.589 --> 00:29:43.170
social issues. But he voted for Trump in 2016.

00:29:43.549 --> 00:29:46.650
He did. He said he agreed with the policies on

00:29:46.650 --> 00:29:49.410
government size and immigration. But he also

00:29:49.410 --> 00:29:51.869
later criticized Trump's rhetoric, calling it

00:29:51.869 --> 00:29:54.750
divisive. So he's not a blind loyalist, but he

00:29:54.750 --> 00:29:57.190
leans right on economics. And he had some strong

00:29:57.190 --> 00:29:59.970
words for the Democrats in 2020. Right. He criticized

00:29:59.970 --> 00:30:02.309
Bernie Sanders and Elizabeth Warren specifically.

00:30:02.789 --> 00:30:05.490
He said their financial policies would destroy

00:30:05.490 --> 00:30:08.289
the fabric of the country. Which, coming from

00:30:08.289 --> 00:30:11.289
a man who defrauded investors of $200 million.

00:30:11.730 --> 00:30:14.670
Is a bold statement on what destroys the fabric

00:30:14.670 --> 00:30:17.250
of a country. Exactly. Don't listen to Bernie.

00:30:17.609 --> 00:30:20.190
He'll ruin the economy. Now let me tell you about

00:30:20.190 --> 00:30:22.289
this penny stock that will make you rich. It

00:30:22.289 --> 00:30:24.609
highlights his worldview. He believes in the

00:30:24.609 --> 00:30:26.589
unchecked market. He believes that regulation

00:30:26.589 --> 00:30:29.130
is the enemy of opportunity, even though regulation

00:30:29.130 --> 00:30:31.450
is the only thing that eventually stop him from

00:30:31.450 --> 00:30:34.390
robbing more people. He views himself as a capitalist

00:30:34.390 --> 00:30:37.369
hero, not a villain. So we've traced the arc.

00:30:37.569 --> 00:30:39.910
We've gone from the styrofoam coolers on Jones

00:30:39.910 --> 00:30:42.720
Beach to the boiler room. We've been in the cell

00:30:42.720 --> 00:30:45.339
with Tommy Chong. We've seen the lawsuits, the

00:30:45.339 --> 00:30:48.099
payouts, or lack thereof, and the reinvented

00:30:48.099 --> 00:30:51.180
guru on stage. It is a heck of a journey. So

00:30:51.180 --> 00:30:53.740
what does this all mean? Why are we so fascinated

00:30:53.740 --> 00:30:56.500
by him? Why did we just spend an hour dissecting

00:30:56.500 --> 00:30:59.059
his life? I think it's because Jordan Belfort

00:30:59.059 --> 00:31:01.539
represents a very specific American conflict.

00:31:02.119 --> 00:31:05.589
On one hand, we value the hustle. We love the

00:31:05.589 --> 00:31:08.349
story of the kid from Queens who makes 20 grand

00:31:08.349 --> 00:31:11.069
selling Italian ice. We admire the salesmanship,

00:31:11.230 --> 00:31:13.410
the ability to generate wealth from thin air.

00:31:13.569 --> 00:31:15.109
We want to believe that we could do it too. We

00:31:15.109 --> 00:31:17.069
want to believe in the magic trick. We want to

00:31:17.069 --> 00:31:19.309
believe there is a shortcut. But on the other

00:31:19.309 --> 00:31:22.369
hand, we despise the fraud. We hate the idea

00:31:22.369 --> 00:31:24.529
of the little guy getting ripped off. Belfort

00:31:24.529 --> 00:31:27.630
forces us to ask, where is the line? At what

00:31:27.630 --> 00:31:31.549
point does sales become scam? And are we complicit

00:31:31.549 --> 00:31:33.569
because we buy the ticket to the movie? Yeah.

00:31:33.920 --> 00:31:35.579
Are we cheering for the bad guy because he's

00:31:35.579 --> 00:31:38.180
charming? It's the magnetism of the villain and

00:31:38.180 --> 00:31:41.099
the reality of forgiveness. Society has, for

00:31:41.099 --> 00:31:43.079
the most part, forgiven him. He is a celebrity.

00:31:43.079 --> 00:31:46.099
He is rich again. We have rewarded the reinvention.

00:31:46.420 --> 00:31:48.940
Which brings me to the final thought. The source

00:31:48.940 --> 00:31:51.599
mentions that Bill Ford's greatest regret is

00:31:51.599 --> 00:31:54.579
losing people's money. He says that in interviews.

00:31:54.839 --> 00:31:58.940
I regret it. He says the words. But actions speak

00:31:58.940 --> 00:32:02.009
louder. He fought the government. tooth and nail,

00:32:02.130 --> 00:32:04.849
to stop paying 50 % of his income to his victims.

00:32:05.369 --> 00:32:08.170
He found the legal loophole. He kept the movie

00:32:08.170 --> 00:32:11.250
money. So it raises the question, has the wolf

00:32:11.250 --> 00:32:13.890
actually changed his stripes? Or did he just

00:32:13.890 --> 00:32:15.950
find a legal way to hunt? I think the sheep should

00:32:15.950 --> 00:32:18.170
probably keep watching their backs. That's a

00:32:18.170 --> 00:32:20.269
wrap for this deep dive. Thanks for listening,

00:32:20.349 --> 00:32:22.150
and we'll catch you on the next one. Bye.
