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An audience with the Wolf of Wall St

Jordan Belfort was one of the most crooked and debauched businessmen in recent history, but claims to have reinvented himself as a motivational speaker specialising in sales techniques. Jenene Crossan has a word to the Wolf.

Writing an article about someone like Jordan Belfort is pretty daunting. Not because the notorious (and now uber-famous) Wolf of Wall Street isn’t interesting, but mostly because, well, what is there really left to talk about? When virtually the whole world has watched in bemused horror and utter astonishment as Leonardo di Caprio plays out the very intimate and full-on adaptation of your life, there’s seemingly not a lot left to cover.

Unsurprisingly, Belfort has reacted accordingly and been on the bender of his life—of the PR variety—wringing out every last cent from this surge in awareness/popularity as a way to help make a dent in his enormous restitution debt (reportedly $200m+). 

For those of you who somehow managed to miss the hype around this man, let me succinctly sum it up: crooked stock trader with a bent for hookers, Quaaludes (sedative-hypnotic “calming” sex drug), fast cars and equally fast women, who took the game too far with his firm Stratton Oakmont and lost 0-1 to the FBI. His hobbies have been known to include dwarf tossing and naked marching bands, and he’s considered one of the best sales motivators in the world. 

I first stumbled across his book back in 2007 and devoured it. There’s no doubt he can confidently add “exceptional story teller” to his LinkedIn profile, because the man can really spin a yarn or two (hundred). It’s all mind-boggling stuff that’s so outrageous you can’t help but wonder how many of the anecdotes are really just delusions brought on by the vast quantities of narcotics he was known for gobbling down like candy. That said, others have vouched for the authenticity of his debauchery and assured the doubters that everything printed and filmed did in fact happen. I guess it’s just so hard to imagine, as it’s so far removed from the kind of lives that most of us lead. I’ve barely met any dwarves, let alone felt compelled to toss them (or any other human being) up against a wall for the entertainment of staff. A sheltered life, I have led.

For Belfort, however, that’s one of the tamer tales. “You know the bachelor party scene in the movie? All true. Single most debauched weekend of my life.” And coming from the man who crashed his $25 million helicopter in his own backyard (due to being under the Quaalude influence), that’s saying something. Don’t ever get into a game of truth or dare with this man. He will win.

Which is exactly why when offered the opportunity to interview him for my blog, I was left pondering what exactly I was going to ask him. Thankfully he made that bit easy with an opening line of “you can ask me anything you want. And I mean ANYTHING”.  What an opportunity. Still, I couldn’t help but wonder what was actually left to ask that he hadn’t already put out there for financial gain and maximum shock factor impact. This man hasn’t exactly left much to the imagination.

So I zeroed in on his sales knack. It’s what’s got him in and out of trouble his entire life and is now at the core of his journey to redemption. He charges up to $30k ?for his Straight Line Persuasion seminars, but gets to pay back investors and gain closure. I’m curious to find out what someone might get out of this.

The thing with interviewing Belfort is that it’s obvious he has a plan in his head; it’s a formula and it’s what he’s sticking to. I guess that’s not surprising, he’s talking it day and night continuously. He knows what he wants me to hear and he’s ‘on’. But what I wonder is that if, as he says, “building rapport” is the single most important element in sales, then surely taking a formulaic approach to being interviewed risks coming across as a touch disingenuous? I can’t help but want to be dazzled by this man, in a fashion similar to how I felt after reading the book and seeing the movie. Perhaps I’m being a little harsh (or expecting a bit much) given you can only imagine that after 300 keynote talks a year (four this week alone), you’d be left feeling a little … empty.

I quiz him on whether you really can teach someone how to build rapport, or is it in fact an innate skill, to which he agrees in part, but is adamant that he can turn a sales pig’s ear into a shiny silk purse. “It’s an entirely learnable skill. Sure, you can find those with natural rapport and teach them strategies and they will take to it faster. But equally, you can find those with no natural rapport-building skills, and with my system, practice and hard work they’ll get results. But most importantly, they need to have the innate desire to begin with. But let’s be honest, I don’t attract those types of kids. It’s the ones who want to be the next big thing who are hungry and driven that I meet.” Fair point, I’m sure there aren’t too many kids waiting for handouts in New York. They’re ambitious folk.

I changed tact into addictions and obsessions. I’m curious as to what’s replaced the nosebag, pills, girls and pots of money and, yip, it’s pretty tame: tennis and talking about himself. Full credit to the guy, he openly admits that speaking is, in fact, his favourite thing to do. “The connection I get from speaking publicly and empowering people has replaced the high I got from closing deals.  Speaking, tennis and cookies, that’s it. I have what I consider healthy addictions; they’re sustainable and they enhance my life, not destroy it.”

This pathway to a healthy mindset is something Belfort refers to often. He teaches understanding who you are and what you are: self-elevation, self-destruction and self-redemption. I ask him about understanding and forgiveness as part of his healing process. “You go through stages like guilt and remorse. The self-serving emotion, guilt, comes first, but when you move past that to remorse and accept the mistakes you made and that good people can do bad things, then you can make a real change in who you are.”

Does he feel like he can hold his head up high today? “I feel guilt every day and I’m working my ass off to pay back the debt and for me that will be full circle.” Upon hearing that and how he phrased it, I can’t help but wonder if the restitution payment is actually less about redemption, and more as a goal that he set himself to mark when he can abscond himself of guilt and remorse. His frequently published remarks about having really only ripped off ‘really rich people’ somewhat illustrates that this is less personal, and perhaps more of an accepted journey or game. 

Belfort has remained adamant that he has turned his life around and that his energy is put towards making good, not nefarious choices. And with that consideration lingering in the air, he’s off for lunch with his fiancée, making the most of the very small amount of downtime he currently allows himself. He leaves me pondering how must the prospect of becoming the next Mrs. Jordan Belfort be, given his extremely public previous relationship with “The Duchess”. Being married to the ex-Wolf of Wall Street would be an interesting ride, that’s for sure. 

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