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Behind the Scenes with the Real Wolf of Wall Street


The Real Wolf Of Wall Street: Meet Jordan Belfort

This week I had the pleasure of interviewing the real Wolf of Wall Street aka Jordan Belfort.

I’m sure you guys have seen the movie…

It’s the crazy true story of how Jordan started a company in Long Island selling penny stocks to anybody who would buy them.

By the age of 26, he grew the firm into a $3 Billion company and had over 1,000 brokers working for him.

Jordan lived a crazy lifestyle of money, hookers, and Quaaludes.

The Wolf of Wall Street film does a great job of showing his excessive lifestyle and those dominating the financial sales industry then (and likely now) but of course the movie couldn’t cover everything.

Jordan really is a fascinating guy so we decided to dig a little deeper.

Who is Jordan Belfort Anyway?

Born and raised in New York City, Jordan Belfort is the quintessential go-getter.

A world-class hustler and salesman who started his career in business at an early age selling Italian ice in the summer to tourists on the city’s boardwalks. From this, he was able to save up and pay his way through college expecting to become a dentist.

As it turned out, dentistry didn’t exactly fit the sensibilities of a man like Jordan so he decided to double down on his obviously significant talents in sales.

He started a company selling meat door to door which is no easy feat and even managed to quickly scale it to a decent-sized business. Things didn’t end up working out though and by the time he was 25 he filed for bankruptcy.

Once free he managed to land a gig on Wall Street through a mutual acquaintance, learning some tricks of the trade which would prove to be invaluable for his future exploits.

Telesales being his primary role on Wall Street is a tough racket. Basically, cold calling someone and persuading them to buy what you’re selling over the phone without any face to face contact takes a unique mix of confidence, charisma, and resilience that few people possess.

Jordan Belfort has proven himself to have all three in spades and so when the markets crashed on Black Monday in 1987 and he got laid off like countless others in the business he took what he learned from Wall Street and a lifetime of sales and pursued a career selling a new product, penny stocks.

For those unfamiliar, penny stocks refer to stocks of small companies available to buy for $5 or less.

Because the stocks are so cheap to buy and the companies are so small, investors lack the information about the company’s inner workings and financials that large, publicly traded companies are legally obligated to provide.

It can therefore be hard to know what you’re getting and it’s a bit like Russian roulette for investors.

Jordan leveraged this lack of information available to those he called to the nth degree.

Like others in the business, he would inflate the value of companies he’d promote to seem like the next promising startup with endless potential.

The difference between Jordan and other penny stocks salesmen is that where they would fail, his sales prowess would turn lead into gold.

Soon after getting into the business, he created Stratton Oakmont and quickly scaled the company. Word spread fast of what he was doing over there and he was continuously attracting more and more hungry brokers with similar ambitions.

The company culture was so notorious that the nickname for Jordan Belfort, Wolf of Wall Street, was born out of his recollections of this period in his life.

The Truth Behind The Wolf of Wall Street Scenes

Arguably one of the most amazing things about all of this is how accurate the movie is about this time in his life.

Of course, there isn’t a public record of everything that went on but much of the memoir for which the movie is based has been shown to be true.

One of the best scenes early in the movie involves Jordan Belfort, played by Leonardo DiCaprio having lunch with Wall Street veteran, Mark Hanna played by Matthew McConaughey in a short and memorable cameo role. The lunch involves Hanna explaining to Belfort the ins and outs of the business emphasizing the need for “masturbation, cocaine and hookers.”

McConaughey’s character Mark Hanna is surprisingly a real person and really was Belfort’s real-life mentor which may help to explain what went on at Stratton Oakmont.

Sex, drugs, and a lack of self-control was rampant throughout the company. This led to infamous office parties, excessive spending, and the attention of the National Financial Regulatory Authority.

Crashing a Lamborghini, helicopter, and sinking a luxury yacht off the coast of Sardinia only to be rescued by the Italian navy all while under several influences will do that and are all surprisingly true.

Even the initial public offering of the shoe company Steven Madden was faithfully recreated in the movie as the massive sales force at Stratton Oakmont managed to aggressively lead the charge for what is still a globally recognized and available brand today.

Mostly what was changed for the movie are some names and the extent to which some characters played a role in the company’s development.

In particular one of the biggest changes is Jonah Hill’s character in the movie Donnie Azoff. In the movie, Jonah Hill’s role in the company was exaggerated to be something of a partner in crime but in real life, his name is Donnie Porush and Donnie has disputed much of the characterization.

Another interesting change is that the nickname ‘wolf of wall street’ seems to have first appeared in the memoir for Jordan’s retelling of this period in his life and was not actually a title given to him by the press during his time at Stratton Oakmont.

Although he was featured by Forbes magazine in an article titled ‘Steaks, Stocks — What’s the difference?’ Referring to his journey as a salesman.

It seems Wolf of Wall Street has a better ring to it.

Overall the mood and tone of the film portraying Stratton Oakmont and Jordan’s life at the time are widely regarded to be true to form.

For instance, although it’s remembered as unlikely that little people were literally tossed around during office parties like in the movie, they were apparently hired regularly for entertainment.

Regardless of what actually happened during these office parties and beyond, there was certainly a significant amount of debauchery that was a regular occurrence in Jordan’s life during this time fueled by his tremendous financial success at such a young age.

Just How Much Was Jordan Belfort worth at the Height Of His Career?

It is not exactly clear just how much Jordan Belfort was worth at the height of Stratton Oakmont.

At one point the company was employing over 1,000 stockbrokers and believed to be trading billions of dollar’s worth of stock issues.

As leader and founder of the operation, he was, of course, afforded the lion’s share of their substantial earnings and certainly wasn’t afraid to flaunt it.

With fast cars, big boats, mansions, and everything else that comes along with the riches, Jordan Belfort lived the life most people couldn’t even dream of.

The film highlights his excessive and vice-filled lifestyle in a tremendously entertaining and re-watchable way of which its director Martin Scorsese does perhaps better than anyone.

There’s a great montage in the movie that highlights some of Jordan’s biggest purchases during this time in his life and they just scratch the surface of what his wealth at the time afforded him.

He could buy nearly anything he wanted in the world and by any measure was a massive self-made success.

However, just like in the movie, the flashy lifestyle and company strategies had quickly caught the attention of government agencies who began building a case for close to a decade.

And in 1999… he ended up being tried for securities fraud and lost everything.

He went to jail for 2 years, lost all his money, and his wife left him.

He had hit rock bottom but amazingly during his time in jail, he shared a cell with Tommy Chong who continuously encouraged him to write a memoir of the amazing life he had lived as a stockbroker.

When he got out of jail, he had to start over from scratch but he had some ideas of where to start again.

The rise and fall… and rise again of Jordan Belfort

Jordan has lived an exceptional life.

Through the ups and downs and twists and turns, his has been a roller coaster ride the likes of which very few people in history have experienced or can even relate to.

His life in the 90s is arguably a modern-day reimagining of the classic story of Icarus flying too close to the sun.

The tale of a person’s ambition becoming so strong that it turns to recklessness and eventually leads to their downfall, intoxicated by confidence and a will to succeed.

Where the archetype and Jordan’s story differ, however, is what happens after the big fall.

As we have seen looking back on Jordan’s life, resilience is a trait he holds strong and we all love a redemption story.

Since his release, Jordan has written two hugely successful books which have been published in over 40 countries and 18 languages.

One of these books became the Oscar-nominated movie of the same name ‘The Wolf of Wall Street’ that we’ve been mentioning and there’s even hope for a possible sequel or follow-up.

He has also been busy touring around the world giving motivational talks, and running sales seminars titled ‘Jordan Belfort’s Straight Line Sales Psychology’ where he shares with salespeople his insights on communication and persuasion.

Certainly skilled in the trade, he is always conscious to warn the attendees of how powerful the tactics are, highlighting his own past experiences as proof.

His sales philosophy is helpful for anyone but as he mentions only if used for good.

He’s also got his own show & podcast called “The Wolf’s Den” which I was on as a guest a couple of weeks ago.

It was a real pleasure to talk with him and learn more about the ups and downs of his journey as an entrepreneur in an effort to find out who is the real Wolf of Wall Street.

If you were a fan of the movie, and want to hear more about his amazing life, you’ll love this interview!

In this conversation, you’ll enjoy 3 BIG things:

  1.   2 early day entrepreneurship stories from before Jordan’s stockbroker days
  2.   Jordan shares his personal stories behind a lot of the scenes from the movie
  3.   We talk about what part of Jordan’s Stock Brokerage firm was a scam, and what part was legit

And if you liked the discussion, I’m sure you’ll love our podcast.

Give it a listen and subscribe at Apple Podcasts or Spotify and also don’t forget to write a review to help spread the word to others just like us interested in marketing, business, and everything else fun under the sun!

Subscribe: Apple Podcasts / Spotify


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