Welcome back to the Deep Dive. Today we are tackling
a subject that, I mean, it feels almost synonymous
with a certain era of American excess. Oh, absolutely.
If I say the wolf, you immediately have an image
in your head. Yeah. Leonardo DiCaprio. You're
picturing Leonardo DiCaprio. You're picturing
a white Lamborghini Countach. You're picturing,
I don't know, lobsters being thrown at FBI agents
on a yacht. You are thinking of the movie. Which
is completely understandable. I mean, that Scorsese
film was a massive cultural phenomenon. It really
did. It turned a financial criminal into a kind
of rock star. Exactly. And that is precisely
why we're here today. We are going to push that
Hollywood glamour aside. We have to. We are stripping
away the cinematic lens to look at the actual
source material regarding Jordan Belfort. And
we have a massive stack of notes here, comprehensive
biographical accounts, actual court documents
regarding restitution, reports on his post -prison
ventures and, you know, the nitty gritty mechanics
of how his schemes actually work. The mission
here is really specific, I think. We aren't here
to retell the party stories. We want to understand
the mechanics. Right. How does a dental school
dropout become one of Wall Street's most notorious
figures? And maybe more importantly, after losing
absolutely everything, his freedom, his money,
his family, how does he manage to sell himself
back to the public? That is the big question.
Yeah. Really is. Is this a genuine redemption
arc or is it just the ultimate sales pitch? We're
going to trace the rise, the reality of the fall,
and the specific details of the restitution and
reinvention that often get overlooked. Because
when you actually look at the documents, the
story is much more complex and frankly a lot
more cynical than the movie suggests. And we
have to start by just acknowledging the source
of our perception, right? Most of what people
know comes from his memoirs, The Wolf of Wall
Street and Catching the Wolf of Wall Street.
So his version. His version, exactly. But as
we go through this, we have to weigh his narrative
against the legal reality. The source material
paints a picture of a man who is, above all else,
a cyclical creature. He builds, he scales, he
crashes, and then he pivots. So let's unpack
this. Let's go right back to the beginning. Before
the Ferraris, before the Quaaludes, we're talking
about Jordan Ross Belfort, born 1962. Raised
in Bayside, Queens. Right. And here is the first
nugget from the file that I think just sets the
stage perfectly. His parents, Max and Leah, were
both accountants. Which is fascinating context,
isn't it? I mean, think about that environment.
Yeah. He grew up in a household where numbers
were the language. You have this Jewish upbringing
in Queens in the 60s and 70s, parents who understand
the ledger, who understand profit and loss, liabilities
and assets. You have to wonder how much of that
financial literacy was just osmosis. He wasn't
learning this from the street. He was probably
learning it at the dinner table. And clearly,
the entrepreneurial itch started early. I love
this story from the source material, but I also
want to scrutinize it a bit. So between high
school and college, Belfort and a childhood friend,
Elliot Lowenstern, they decide they're going
to hustle. They head out to Jones Beach. A classic
New York summer spot. A classic. And they aren't
just hanging out. They are selling scooped Italian
ice from styrofoam coolers. Now, the source says
they made $20 ,000. In a single summer. Okay,
let's just pause and do the math on that because
that number sounds insane for a couple of teenagers.
It does. We are talking about the early 1980s.
Adjusted for inflation, that $20 ,000 back then
is roughly equivalent to nearly $75 ,000 today.
That is a staggering amount of cash for two kids
on a beach. Right. I mean, when I was a teenager,
a summer job meant making minimum wage bagging
groceries. Yeah. Maybe you'll walk away with
a couple grand if you're lucky. These two walked
away with the equivalent of a mid -level corporate
salary. How is that even physically possible?
I know. Were they selling the ice for $50 a scoop?
What was going on? It's a volume game, and it's
a territory game. If we really analyze this,
it's the first real sign of his sales DNA. It
implies a few things. One, they weren't just
selling a product. They were exploiting a captive
market. Okay. You have hot people on a beach,
dehydrated, looking for sugar. The demand is,
you know, it's inelastic. Two, to move that much
product, we're talking thousands and thousands
of scoops, requires serious logistics. I hadn't
even thought of that part. You have to keep the
ice frozen in styrofoam coolers in the baking
sun. You have to transport it. You have to hustle
up and down the sand. It establishes that he
wasn't afraid of the grind. Not at all. Carrying
styrofoam coolers up and down Jones Beach isn't
glamorous work. It's heavy. It's messy. But the
margin was clearly there. Exactly. And it highlights
his ability to spot a gap. It wasn't about the
Italian ice itself. He didn't care about the
culinary quality of it. No. It was about the
arbitrage. Buy low, sell high, high volume. That
is the blueprint for everything that comes later.
So he has this pile of cash, this small fortune.
For a kid his age. And he heads to American University,
gets a degree in biology, believe it or not.
Which is a surprise to a lot of people who just
assume he studied finance or economics or something.
Right. But then comes the pivot that changes
everything. He takes that Italian ice money,
and he enrolls in the University of Maryland
School of Dentistry. He had a plan. He did. But
this is where the story takes a really sharp
left turn, and I want to get your take on whether
this sounds like a true story or a wolf embellishment.
Okay, let's hear it. It's day one at dental school.
The dean gives the welcoming speech to the incoming
class, and he says, and I'm quoting the source
here, the golden age of dentistry is over. If
you're here simply because you're looking to
make a lot of money, you're in the wrong place.
That is the legendary quote. Belford hears this
and he drops out. Immediately. It's a very cinematic
moment, isn't it? It feels almost too perfect.
Yeah. I walked out the door right then and there.
Do we buy that? Did it happen exactly like that?
Well, you know, whether it happened that dramatically
or whether it took him a week to process it,
the outcome is the verified fact. True. He did
drop out almost immediately. And I think even
if he polished the anecdote for the book, the
psychology behind it is real. How so? Most people
go to dental school because they want to be dentists
or they want the prestige or they have some desire
to help people. For Belfort, the career was purely
a vehicle. It was a vehicle for a financial outcome.
Right. It was just a means to an end. Once the
dean removed the promise of making a lot of money,
the vehicle was useless to him. It's like buying
a car to win a race and then finding out the
car has no engine. You don't just sit in it.
You get out. It crystallizes his motivation perfectly.
It wasn't about the work. It was about the wealth.
So dentistry is out. What does he do next? He
goes into sales. Specifically, door -to -door
meat and seafood on Long Island. This is the
first legitimate adult business venture we see
in the records. And again, look at the pattern.
He creates a business called the Meat and Seafood
Business. Not a very creative name. No, but descriptive.
And he doesn't just sell a few steaks to housewives
here and there. He scales it. He scales it aggressively.
He claims he grew this business to employ several
workers. They were moving 5 ,000 pounds of beef
and fish a week. Let's just contextualize 5 ,000
pounds. Please. That is two and a half tons of
perishable product. Right. Weekly. In the 1980s,
this isn't clicking a button on an app to order
more inventory. No. This is physical inventory.
You need trucks, you need freezers, you need
drivers. And you need to sell it before it spoils.
Precisely. It is a high -pressure logistical
nightmare. And he's doing this door to door.
But here's the foreshadowing. He scales it up,
moving massive volume, and then it collapses.
Poof. He falls for bankruptcy at age 25. Why
do you think that happened? What went wrong?
Well, looking at the retrospective analysis,
it really suggests a focus on aggressive expansion
sales, sales, sales without the underlying capital
structure to support it. So selling faster than
he could actually manage. Exactly. He was likely
extending credit to customers or buying inventory
on credit that he couldn't pay back fast enough.
It establishes this boom and bust cycle, rapid
scaling, followed by a total crash. And he was
25 years old. and already bankrupt. That could
have been the end of the story for a lot of people.
It's a humiliating failure. You're back at square
one. But for Belfour, it seems like it was just
the warm -up. Uh -huh. So he's broke, he's 25,
a family friend pulls some strings and gets him
a trainee job at L .F. Rothschild, a real, you
know, blue -blooded Wall Street firm. Finally,
he is in the arena. But talk about bad timing.
He gets there, he starts trading, he's ready
to become a master of the universe, and then
wham! Black Monday. The stock market crash of
1987. Right. October 19, 1987. The biggest one
-day percentage drop in stock market history.
The Dow dropped 22 .6%. It was just chaos. It
was. And L .F. Rothschild was hit hard. I mean,
really hard. They started laying people off left
and right. And Belfort. Being the low man on
the totem pole was laid off almost immediately.
So the universe is really testing him here. Dentistry?
No. Meat business. Bankrupt. Wall Street. The
market literally crashes the moment he arrives.
But this is the crucial pivot point. This is
where the wolf is actually born. How so? Because
he can't play in the big leagues anymore. The
big leagues are bleeding. L .F. Rothschild isn't
hiring. Goldman isn't hiring. So he looks at
the underbelly. He finds a job at a small brokerage
center on Long Island selling penny stocks. And
this leads to the founding of Stratton Oakmont.
Now, originally, this was a franchise of something
called Stratton Securities, right? It wasn't
his name to start. Correct. He started as a franchisee,
which is an interesting detail. He didn't invent
the name immediately, but eventually he buys
out the original founder and makes it his own.
And this is where we need to explain what Stratton
Oakmont actually was. Yes. Because in the movie,
it just looks like a chaotic party where people
are screaming into phones. But structurally,
it was a boiler room. Let's break that down for
the listener who might hear that term but not
know the mechanics. What is a boiler room specifically?
A boiler room is basically an outbound call center
that sells questionable investments using high
pressure sales tactics. They are literally turning
up the heat on the investor. The term refers
to the high pressure environment and often the
physical location. Originally, these scams were
run out of cheap basement offices, you know,
near the boiler room of a building. And Stratton
Oakmont specialized in marketing penny stocks.
Right. Penny stocks are shares of very small
public companies that trade at very low prices,
usually under five dollars a share. They're highly
volatile, thinly traded and very easy to manipulate
because there isn't much public information about
them. And the specific fraud they were running
is. known as pump and dump i want to walk through
this step by step so we understand exactly how
the theft happened okay let's look at the mechanism
described in the text it starts with the setup
belfort and his partners stratton oakmont would
acquire a huge position in a cheap stock sometimes
they would control nearly the entire supply of
the stock through what are called nominee accounts
or rat holes rat holes that sounds pleasant It
means they own the stock, but it's hidden in
accounts under other people's names, so it doesn't
look like Stratton Oakmont owns it all. Got it.
That's step one. Step two is the pump. Belfort's
army of brokers gets on the phones. And they
had a very specific script for this, didn't they?
I read about the Kodak pitch. This is the genius
and the evil of the sales tactic. They wouldn't
start by selling the garbage stock. They would
call a potential client, often a blue -collar
guy or a small business owner, and pitch a blue
-chip stock. Something safe like Kodak or IBM
or Disney. Mr. Smith, Kodak is poised for a breakout.
Why do that? Why sell a legitimate stock first?
To build trust. It's brilliant in a sinister
way. If you buy Kodak and it goes up a few bucks,
you think, hey, this broker knows his stuff.
You trust him. You think he's on your side. Belfort
called this papering the client. So once the
client is papered and trusts the broker, then
comes the switch. Exactly. Then comes the call
for the house stock. the garbage penny stock
that Stratton Oakmont secretly owns. The broker
calls back breathless with excitement. Mr. Smith,
I have something incredible. It's a small company.
It's about to explode, but you have to move now.
That urgency, the scarcity. It's classic psychological
manipulation. The client, who now trusts the
broker, dumps his savings into this penny stock.
And that's the bump. The price of the stock skyrockets
because of this artificial demand created by
the call center. And then? Then comes the dump.
Once the price hits a peak, Stratton Oakmont
and Belfort personally sell off their hidden
holdings. They dump millions of shares into the
market. Which kills the price. It obliterates
it. The supply floods the market. The price crashes
to zero. Belfort walks away with millions in
cash. The investors, Mr. Smith in Ohio, the retiree
in Florida, are left holding stock that is literally
worthless. They lose everything. It's a direct
transfer of wealth from the gullible to the manipulator.
Correct. And the scale of this was unbelievable.
The source says at one point, Stratton Oakmont
employed over one... thousand stockbrokers. A
thousand brokers. Imagine the noise in that room.
Imagine the energy required to keep a thousand
people lying on the phone all day. And they were
involved in stock issues totaling over a billion
dollars. A billion with a B. Including, famously,
the IPO for Steve Madden Footwear. That was their
crown jewel. Steve Madden was a legitimate company.
They actually made shoes. Taking them public
gave Stratton Oakmont a veneer of credibility.
Right. Look, we aren't just selling penny stocks.
We took Steve Madden public. But even that IPO
was manipulated behind the scenes to ensure Belfer
and his cronies controlled the share price from
the jump. Now we have to talk about the culture
that fueled this. Because you can't have a thousand
young men ripping people off all day without
a certain atmosphere. Oh yeah. The source material
describes a life of lavish parties and intensive
use of recreational drugs. Specifically methaqualone.
Qualudes. The source mentions his addiction to
qualudes explicitly. And this is where the movie
leans in heavily. But from an analytical perspective,
we have to look at what that drug does. Qualudes
are a sedative hypnotic. They lower inhibitions.
They make you feel invincible. They numb the
moral center. Is that a fair way to put it? In
a way, yes. When you are operating a billion
dollar fraud while addicted to heavy sedatives,
your risk assessment is completely broken. Yeah.
You stop worrying about the SEC. You stop worrying
about the FBI. You feel like a god. That drug
-fueled invincibility likely accelerated the
fraud. It pushed them to be more brazen, more
reckless. So you have this boiler room. You have
a thousand brokers. You have drugs. You have
money pouring in. But you also have eyes on you.
The government isn't blind. The regulatory cat
and mouse game had to begin. The source says
Stratton Oakmont was under near constant scrutiny.
from the NSD, which is now Fine RA, from 1989
onward. That is almost the entire existence of
the firm. It was. They were fighting regulators
constantly. Belfort spent a fortune on lawyers
to delay, to obfuscate, to pay fines and just
keep going. But the wheels finally fell off in
December 1996. The NASD expelled Stratton Oakmont.
They effectively put the firm out of business.
But the criminal charges took a bit longer. It
wasn't until 1999 that Belfort was indicted for
securities fraud and money laundering. And this
leads to the next major pivot in his life. The
pivot from wolf to rat, if you want to use the
street terminology. Because in the movies, not
just the Belfort movie, but crime movies in general,
there's this code of silence. Omerta, you don't
snitch. You do your time. That is not what happened
here. Not at all. Not at all. The source material
is very clear. Jordan Belfort became an FBI informant.
He didn't just talk. He wore a wire. He wore
a wire against his partners and associates. He
gathered evidence. He testified against them.
I just want to pause on the reality of that for
a second. Wearing a wire isn't simple. You are
walking into a room with your best friends, people
you have partied with, done drugs with, committed
crimes with. And you're actively recording them
to send them to prison. It's a profound betrayal.
But it's also, it's a rational calculation. Hell
so. Belfort is a salesman. He deals in transactions.
The deal on the table from the FBI was, you are
looking at 20 or 30 years in prison. Yeah. Give
us everyone else and we will give you a discount.
And he took the deal. He did the math. He realized
his friends were a depreciating asset, and his
freedom was the only thing that mattered. He
sold out his friends to buy his freedom. And
the discount was significant. Let's look at the
sentence. He was sentenced to four years. Which,
for a fraud of this magnitude, investor losses
estimated at $200 million is remarkably light.
It's nothing. There are people serving longer
sentences for selling small amounts of marijuana.
But he didn't even serve the four years. No,
he served 22 months. 22 months. He did less than
two years for a $200 million fraud. At the Taft
Correctional Institution in California. And let's
be clear about Taft. This isn't Rikers Island.
No, it's often referred to as club fed. It's
a low security camp, no bars on the windows,
dorm style living. But still, it is a loss of
freedom. And this is where the story gets really
weird. Because you think, okay, he's in prison,
he's disgraced, the party is over. But even in
prison, the universe throws him a lifeline. Or
rather, a cellmate. This is one of those facts
that if you wrote it in a screenplay, a producer
would tell you to cut it because it's too unbelievable.
Right. His cellmate was Tommy Chong. As in Cheech
and Chong, the guy from Up in Smoke? The stoner
comedy icon. Chong was in there for a paraphernalia
charge -selling bongs online, essentially. Which
was a huge controversy at the time. So you have
the Wolf of Wall Street and Tommy Chong sharing
a bunk in California. And they're swapping stories.
I'd love to have been a fly on that wall. Exactly.
Belfort is telling these wild tales about the
midget tossing, the yacht sinking, the drugs,
and Chong is just listening. And Chong is the
one who says, hey, you should write this down.
Chong told him, this is a book. You are a natural
storyteller. You need to write your memoirs.
Chong basically coached him into his next career.
So Belfort starts writing. The source says he
actually wrote and destroyed 130 pages at first,
a false start. He tried to write it like a novel,
and it was bad. But eventually, he finds his
voice. He produces The Wolf of Wall Street and
Catching the Wolf of Wall Street. And the commercial
instinct kicks in again. These books were published
in roughly 40 countries, translated into 18 languages.
And here's the kicker. A bidding war for the
film rights began before the first book was even
released. He hadn't even published the book yet
and Hollywood was already throwing money at him.
Wow. It just shows the undeniable appeal of the
story. Studios and new audiences would eat up
this tale of debauchery. But we have to pause
here and look at the fact versus fiction aspect.
Because Belfort is the narrator of his own life.
And he has a history of, let's call it, creative
truth. He is a notoriously unreliable narrator.
The former federal prosecutor who led the investigation
is quoted in our source material. He said that
Belfer invented much and aggrandized his importance.
Aggrandized his importance? The man who calls
himself the wolf. I'm shocked. Chuckles. Right.
But the prosecutor's point is crucial. He emphasized
that the real story isn't just the parties and
the fun. It involves thousands of victims who
lost their savings. Yeah. When we get swept up
in the narrative of the wolf, we forget the sheep,
the people who got slaughtered financially. The
book makes it funny. The reality was tragic for
the victims. That is a perfect segue into the
money trail because part of his sentence wasn't
just time. It was restitution. He was ordered
to pay back $110 .4 million to his victims. victims.
Correct. That was the legal debt. So let's look
at the scorecard. As of 2013, which is years
after his release, how much had the victims recovered?
About $10 million. Out of $110 million. That
is less than 10%. And most of that $10 million
didn't come from Belfort writing checks. It came
from the sale of forfeited properties, houses,
cars that the government seized early on. It
wasn't coming from his new income. This brings
us to the 50 % dispute. This is a legal battle
that really highlights how Belfort operates.
I want to dive into the legalese here because
it shows his mindset. It does. So his original
sentencing agreement stated he had to pay 50
% of his gross income toward restitution. That
sounds like a lot, right? Half of everything
you make goes to the victims. Right. If you make
a million, the victims get $500 ,000. Seems fair.
But in 2013, federal prosecutors filed a complaint
saying he was in default. They claimed he wasn't
paying. And Belford's lawyers had a very technical
argument. A very technical argument. They argued
that the 50 % requirement was only valid during
his parole. Technically, it's called supervised
release. His supervised release ended in 2009.
Therefore, his lawyers argued, once that supervision
period ended, the contractual obligation to pay
50 % That is bold. I'm off parole, so I don't
have to give you half my money anymore, even
though I still owe $100 million. It's legalistic
jujitsu. And the judge agreed, or at least ruled,
that the specific 50 % requirement had expired.
with the supervision, so they had to strike a
new deal. What was the new deal? He has to pay
a minimum of $10 ,000 per month for life. $10
,000 a month. Now, for the average listener,
$10 ,000 a month is a huge amount of money. Sure.
But for a guy who claims to make millions in
speaking fees, it's a drop in the bucket. Let's
do the math. $10 ,000 a month is $120 ,000 a
year. To pay off the remaining $100 million,
it would take roughly 833 years. So the victims
are never getting that money back. Mathematically,
no. Unless he voluntarily writes a check for
$100 million, the victims are out of luck. And
there was also a controversy regarding the movie
Royalties, right? I remember seeing him claim
he was giving all the money to the victims. He
went on TV and said it. He did claim that. On
his website, on Facebook, in interviews, he said,
I am not making a dime from the movie or the
books. I am turning over 100 % of the royalties
to the victims. That sounds noble. That sounds
like redemption. It does. But the U .S. attorney
stepped in and filed documents saying that claim
was not factual. They pointed out that he had
received money from the initial sale of the film
rights and kept it. Businessweek had a report
on this that was pretty damning. Yes. They reported
that before the movie release, out of roughly
$1 .2 million he received, he had paid only $21
,000 toward restitution. $21 ,000 out of $1 .2
million. That's not even 50%. That's not even
2%. So there is a massive gap between the redemption
brand, the guy who says I'm giving it all back,
and the financial reality. He was keeping the
vast majority of the cash while telling the public
he was a martyr for his victims. That gap brings
us to his current career. Reinvention. He didn't
go hide in a hole. He didn't retire quietly.
he pivoted to motivational speaking and sales
training. He became a guru. And markets it as
Jordan Belfort's straight -line sales psychology.
Which is incredibly ironic if you think about
it. He is teaching the straight -line system.
Is that a new system? Did he invent this post
-prison? No, that is the exact same sales technique
he developed at Stratton Oakmont. It is the system
he used to train those 1 ,000 brokers to defraud
people. He has repackaged the weapon of the crime
as a legitimate business tool. And people are
paying for it. They're paying a lot. His speaking
fees range from $30 ,000 to $75 ,000 per engagement.
His sales seminars can cost $80 ,000 or more
for corporate training. Who is paying that? Who
hires a convicted fraudster to train their sales
team? That is the fascinating market question.
It's a mix. You have aspiring entrepreneurs who
see his wealth and want the secret. You have
legitimate companies who think, well, say what
you want about his ethics. The guy knows how
to close a deal. They want the technique without
the jail time. They think they can strip mine
the skill and leave the fraud behind. It's dangerous
territory. It is. Because the technique itself,
the high pressure, the psychological manipulation
is inherently aggressive. And speaking of dangerous
territory, the source mentions a scandal in Australia
that sounds suspiciously familiar. This is something
that often gets buried under the movie hype.
This is a really important detail. The Australian
training scandal. Tell me about this. What happened
down under? An investigation by 7 News and the
Sunday Mail in Australia found links between
Belfort and a company called Face -to -Face Training
and another called Career Pathways Australia.
Belfort gave workshops for the staff of these
companies. He was the brand ambassador. He promoted
them heavily. And what was the business model
of these companies? They were vocational training
companies. In Australia, the government provides
funding for worker training. Ah, government money.
Yeah. Always a target. Right. So face to face
training was receiving millions in state government
funding to train employees. But the investigation
alleged that the training never happened. A ghost
training program. Nine News Australia called
it a tick and flick scam. Tick and flick. What
does that mean? You tick the box to say someone
was trained. You flick the paperwork to the government
and you collect the check. The employees never
got the training. But the company got the funding.
And Belfort was involved with them. He was the
face of their workshops. He was training the
people who are running this scheme. Now, to be
fair, the source doesn't say Belfort was the
architect or the owner of that specific scam.
OK, so he wasn't charged with anything. No, he
wasn't charged, but he was in the orbit of it.
He was a paid associate of a company accused
of a multimillion dollar fraud against the government.
That pattern again. Exactly. He finds himself
adjacent to or directly. involved in situations
where value is being faked and money is being
extracted from a large faceless entity. First,
it was investors. Then it was the Australian
government. It's like he has a magnet for it.
Or maybe he is the magnet. It suggests that even
in his legitimate phase, he attracts operators
who cut corners. Precisely. Birds of a feather.
Let's shift gears to his modern moves. Because
a guy like Belfort. has to stay on the cutting
edge of money. What is the cutting edge right
now? Crypto, of course. Of course. And his journey
with cryptocurrency is classic Belfort. A flip
-flop. A total 180. Originally, back around 2017,
he was a massive skeptic. He called Bitcoin freaking
insanity and mass delusion. He was on TV telling
people to get out before they lost everything.
I remember that. He was warning people away from
it. He sounded like the voice of reason for a
minute. But then prices skyrocketed. The market
cap hit trillions and suddenly the wolf changed
his tune. Now he is an inventor in crypto startups.
He has pivoted to being a crypto bull. Why the
change? Did he suddenly understand the technology
better? Cynically. I think he saw where the money
was. Yeah. Belfort chases liquidity. When the
money was in meat, he sold meat. When it was
in penny stocks, he sold stocks. Now the money
is in crypto, so he sells crypto wisdom. But
the blockchain bit him back. It did. In 2021,
a hacker stole $300 ,000 in digital tokens from
his crypto wallet. There is a certain irony in
the wolf getting robbed. There is. He was very
vocal about it, very angry. But it shows that
even the master can get played in this new Wild
West. I also want to touch on the yacht incident.
Yeah. Because the sinking of the Nadine is such
a perfect metaphor for his hubris. The source
gives us some specific details on this that are
just wild. Yes. The yacht, the Nadine. And you
know who it was originally built for? No. Poco
Chanel. Get out. I did not know that. That's
a piece of genuine history. It was a beautiful
historic vessel and Jordan Belfort sank it. Ego.
Pure ego. He insisted on sailing into high winds
off the coast of Sardinia. The captain, the expert,
the guy who actually knows how to sail, advised
him against it, said it was dangerous, said the
wingers were too high. And Belfort. Belfort overruled
him. He essentially said, I'm the wolf. I control
the weather. Full steam ahead. And nature didn't
care about his ego. The waves smashed the foredeck
hatch. The yacht took on water and sank. It's
at the bottom of the Mediterranean. And everyone
on board. They all had to be rescued by Italian
Navy Special Forces. It's the Stratton Oakmont
story in miniature. Ignore the rules. Ignore
the experts. Push full throttle until the whole
thing goes under. And assume someone will come
rescue you. Which, in both cases, they sort of
did. He survived the yacht sinking and he survived
the prison sentence. He always seems to have
a life raft. Let's touch... Briefly on his politics
before we wrap up, because for a guy who lives
such a chaotic life, his political views are
interesting. They are a mix. In the 90s, he donated
to the Republican Party $100 ,000. OK, straightforward
enough. But socially, he describes himself as
a liberal at heart. He's pro -choice, things
like that. He's not a staunch conservative on
social issues. But he voted for Trump in 2016.
He did. He said he agreed with the policies on
government size and immigration. But he also
later criticized Trump's rhetoric, calling it
divisive. So he's not a blind loyalist, but he
leans right on economics. And he had some strong
words for the Democrats in 2020. Right. He criticized
Bernie Sanders and Elizabeth Warren specifically.
He said their financial policies would destroy
the fabric of the country. Which, coming from
a man who defrauded investors of $200 million.
Is a bold statement on what destroys the fabric
of a country. Exactly. Don't listen to Bernie.
He'll ruin the economy. Now let me tell you about
this penny stock that will make you rich. It
highlights his worldview. He believes in the
unchecked market. He believes that regulation
is the enemy of opportunity, even though regulation
is the only thing that eventually stop him from
robbing more people. He views himself as a capitalist
hero, not a villain. So we've traced the arc.
We've gone from the styrofoam coolers on Jones
Beach to the boiler room. We've been in the cell
with Tommy Chong. We've seen the lawsuits, the
payouts, or lack thereof, and the reinvented
guru on stage. It is a heck of a journey. So
what does this all mean? Why are we so fascinated
by him? Why did we just spend an hour dissecting
his life? I think it's because Jordan Belfort
represents a very specific American conflict.
On one hand, we value the hustle. We love the
story of the kid from Queens who makes 20 grand
selling Italian ice. We admire the salesmanship,
the ability to generate wealth from thin air.
We want to believe that we could do it too. We
want to believe in the magic trick. We want to
believe there is a shortcut. But on the other
hand, we despise the fraud. We hate the idea
of the little guy getting ripped off. Belfort
forces us to ask, where is the line? At what
point does sales become scam? And are we complicit
because we buy the ticket to the movie? Yeah.
Are we cheering for the bad guy because he's
charming? It's the magnetism of the villain and
the reality of forgiveness. Society has, for
the most part, forgiven him. He is a celebrity.
He is rich again. We have rewarded the reinvention.
Which brings me to the final thought. The source
mentions that Bill Ford's greatest regret is
losing people's money. He says that in interviews.
I regret it. He says the words. But actions speak
louder. He fought the government. tooth and nail,
to stop paying 50 % of his income to his victims.
He found the legal loophole. He kept the movie
money. So it raises the question, has the wolf
actually changed his stripes? Or did he just
find a legal way to hunt? I think the sheep should
probably keep watching their backs. That's a
wrap for this deep dive. Thanks for listening,
and we'll catch you on the next one. Bye.