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How Jordan Belfort finally figured out his ‘why’ (with video)

(Photo: FreightWaves)

Jordan Belfort believes that anyone can achieve greater success than they imagine themselves capable of if only they learn some essential skills and discover their ‘why’ – a core value or commitment that provides abiding motivation. 

For Belfort, the notorious stockbroker and principal at Stratton Oakmont whose rise, fall and rise was immortalized in The Wolf of Wall Street (2013), the ‘why’ turned out not to be quaaludes, womanizing or money, but the unconditional love he felt for his children. It just took a 22-month stint in prison for fraud to get him there.

In a humorous, wide-ranging interview on the stage at FreightWaves LIVE in Chicago, Belfort and FreightWaves president George Abernathy discussed Belfort’s life, successes, mistakes and lessons learned.

Amid stories of multiple ex-wives, yacht crashes, cellmates and Hollywood, a theme emerged – you are not merely the sum of your past experiences and mistakes, Belfort said – “that’s a load of bullshit.” Instead, Belfort realized, his story “goes to show you the power you have over your own life, especially when things don’t go your way.”


That was the human-centered, motivational core of Belfort’s message, but Abernathy also asked him about the advantages of a high-energy sales culture and how to generate leads in the internet age.

“In the beginning [of Stratton Oakmont] there was was positive energy,” Belfort recalled. “We took young kids from poor families, taught them a system of selling, made them incredibly effective on the phone. It was a great place, but there were things that went on that weren’t right. It was a culture that was success-oriented and working toward a common vision, with no room for negativity; any negativity was overwhelmed by positivity.”

One of the fundamental changes in selling that has occurred over the last 10 years, Belfort said, was that internet-driven inbound lead generation has made sales forces vastly more efficient. Instead of the top of the sales funnel being dominated by hundreds of cold calls per day, now salespeople can begin the process by contacting leads who are already interested in what they’re selling. 

The granular segmenting and targeting enabled by social media platforms, in particular Facebook and Instagram, generates a quantifiable and predictable return on ad spend, Belfort said. But right now he’s enamored with TikTok, the social video platform beloved by teenagers.


“Whatever your IQ is, it goes down as you watch it,” Belfort laughed. “It’s people doing stupid shit. It almost defies imagination.” But what Belfort likes about TikTok is that it’s still a young platform with immature algorithms that give content creators a vast reach on the cheap.

It wasn’t always easy for Belfort to find an audience. Even though he was a talented verbal communicator, he struggled to tell his story in writing. His cellmate, comedian Tommy Chong, encouraged him, but was also a harsh critic of early drafts of Belfort’s book. 

Languishing in prison, Belfort became desperate to redeem himself in the eyes of his children, so he systematically studied the prose styles of Tom Wolfe’s Bonfire of the Vanities and Hunter S. Thompson’s Fear and Loathing in Las Vegas, two gonzo accounts of excess and debauchery. 

What was fascinating about Belfort’s account of learning how to write was his story of an old dog learning new tricks. At Stratton Oakmont, he developed a high pressure sales system that any motivated new hire could learn and use to make a lot of money, but one gets the idea, watching Belfort on stage, that selling came easily to him. Writing was different. 

The experience of developing a writing voice and then the success the book found with publishers is Belfort’s second act, where he commits himself to the hard work of learning the skills he knows he needs to find success again. Belfort’s evolution as a writer is inspiring because it didn’t come easy and because it serves as further proof of his belief that people are more capable of learning new skills than they think.

Ultimately, though, Belfort concluded that it wasn’t mere ‘motivation’ that powered him to a new career in writing, content creation, and sales training.

“Remember this – motivation unto itself is like a warm bath,” Belfort said. “It feels good, you should take one every day, but it doesn’t do that much for you.”

“I had a powerful ‘why,’” Belfort said. “I knew why I had to come back – not for money or for fame, in those moments when I thought I couldn’t go on, I saw the faces of my two kids. I came back for my kids. That was my ‘why.’ Once you know your ‘why’ – a cause you believe in, someone you love unconditionally – once you tap into the power of your ‘why’ and you learn those skills, you become an unstoppable force, and everyone here is capable of doing that.”


John Paul Hampstead

John Paul conducts research on multimodal freight markets and holds a Ph.D. in English literature from the University of Michigan. Prior to building a research team at FreightWaves, JP spent two years on the editorial side covering trucking markets, freight brokerage, and M&A.