5 Invaluable Lessons from a Trailblazing Multimillionaire

We recently had the opportunity to hear Jesse Itzler speak at an industry event and it was both entertaining and inspiring. You may recognize Itzler as the author of the New York Times best-selling book “Living with a Seal.” The experience of having a U.S. Navy Seal move in with him, his wife Sara Blakely (founder of Spanx) and family is just one chapter in his extraordinary life. Aside from his success as a writer, Itzler is an accomplished entrepreneur.

  • He became an MTV rapper despite the fact that he didn’t know how to play an instrument, had no connections in the music industry and by his own admission, didn’t have a great voice.
  • He launched and sold to Warren Buffett a jet company named Marquis Jets even though he had zero aviation experience.
  • He founded and sold a company that writes theme songs for sports franchises.
  • He partnered with a coconut water company, Zico, which was eventually sold to Coca Cola.
  • He’s a determined endurance athlete who has climbed to the summit of Mt. Washington in winter and ran over 100 miles in a single day.
  • He’s the owner of the Atlanta Hawks.

While entertaining our group with some outlandish tales of his entrepreneurial adventures, he dropped a few nuggets of wisdom we can all learn from. Here are five of them.

Find Your Point of Differentiation

What set Itzler on this journey of incredible accomplishments was a college class presentation on selling brownies. That never came to fruition but the lesson learned from his instructor during his less-than-stellar presentation in class was invaluable and it’s been the driving force behind all of his endeavors.

A mere 30 seconds into his class presentation, the professor stopped him and said, “Son, I want to know what your point of differentiation is? How is your brownie different from all the other brownies on the market? If you want to make it and be great and have a long-lasting, successful, scalable business, your brownie has to be different from all the other brands on the market. Sit down.”

From that point forward, Itzler focused on his point of differentiation when launching new businesses. “I’ve always asked myself, what makes me different?”

Don’t Let Off the Gas

By the mid ‘80s, rap had become more mainstream featuring artists like Run DMC, Tone Loc, and Young MC. There was, however, a shortage of white rappers in the business which was Itzler’s point of differentiation. But he needed more than his skin color to break into the business. He had heard that the owner of Delicious Vinyl, an LA record label that signed and promoted hip hop artists, happened to be a huge fan of another rapper, Dana Dane, from Brooklyn, N.Y. So he called the offices of Delicious Vinyl and got the owner’s assistant on the phone. As he tells it, Itzler said the assistant might have been a little confused. After a brief hold, she came back on the phone and said, “Dana, Mr. Ross is so excited to see you. If you could be here at two o’clock, Mike would love to buy you lunch.” Itzler responded with, “Dana, will be there at two o’clock.” Keep in mind that Itzler did not know Dana nor had he ever met the rapper. Nonetheless, he showed up promptly at two and was whisked into a room to wait for the owner.

“I’m sitting on a chair in his office, no agenda. I just want to get my demo heard. And in comes Mike Ross. And he looks at me and he says, ‘who in the world are you?’ I said ‘I’m Jesse. I work with Dana.’ He said, ‘you work with Dana, what do you do?’ I said, ‘I rap. While we wait for Dana. Do you mind I put my demo in?’” After 30 seconds, Itzler had a record deal. Using the stage name Jesse James, his first single, “Shake it Like a White Girl,” made it to number 74 on Billboard’s Hot 100 chart and was featured in the 2004 move “White Chicks.”

And this is when he learned an important life lesson. After reaching his goal of becoming a rapper with a record deal, he became complacent. “I took my foot off the gas pedal,” he said. “When you get momentum, that’s when you have to step on the gas, accelerate and double down. When you hit a goal, you check that box and you set higher goals. And that’s how you get separation from the competition. I did the opposite and got dropped from the label.”

Find Your Purpose

Itzler’s wife, Sara Blakely, often says that you find your true purpose at the intersection of these three things:

  • What you love to do
  • What you’re good at
  • Providing a product or service that helps people


After being dumped by Delicious Vinyl, Itzler realized that he loved sports and he loved music. So he married the two and wrote a theme song for the New York Knicks, “Go NY Go,” which became wildly popular among fans. Because of the song’s popularity, the NBA hired him to create the “I Love This Game” slogan and campaign. This business grew and after three years was bought by SFX Entertainment. Which brings us to his next nugget of wisdom.

Create Your Own Luck

Wiggling his way into the studio of a record label is one example of creating your own luck. “You put yourself in a position where luck will find you – you attract luck,” he said. “Luck happens when you put yourself out there.” Itzler put himself in a position to have his demo tape heard by an executive in the music biz and wound up with a record deal.

He also explained how he actually lost money creating and recording the Knicks’ theme song. “The Knicks paid me $4,000 to do the song. By the time I paid the studio engineer, singer, producer, drummer, the lawyer, it cost me $4,800. Is that a good business model?” he asked us which was met by a resounding “no” throughout our group.

“Wrong,” he said. “That’s an amazing business model. Because when you start out, people buy into people, stories and momentum more than they do products. You’re the business plan. You are the business plan. I would have paid the next $5,000 to say they were my customer.”

 Establish Credibility

After successfully building a business that wrote theme songs for a number of professional sports teams, he and his partner were invited on a private jet with the owner of SFX, a public company that eventually bought out Itzler’s theme song business. The very luxurious private jet was part of a fleet that belonged to a time-share company owned by Warren Buffett. His next big idea was sparked from that plane ride. After experiencing how the wealthy travel, the 27-year-old Itzler and his partner decided they wanted to travel like that whenever they flew. Marquis Jets was born from the idea that other people might like to fly on private jets without the hassle or expense of actually owning one. The idea was it worked like a debit card – if you purchase 25 hours of flight time and took a two-hour flight, you’d still have 23 hours left. Marquis Jets would cover the cost of the pilot, maintenance, fuel and scheduling.

Still, Itzler didn’t have a fleet of private jets. Heck, he didn’t even have any experience in aviation. Yet he was convinced his plan would be successful. So he managed to get an audience with the CEO of Warren Buffett’s company NetJets and pitched his idea. Instead of a boring PowerPoint presentation, Itzler brought a focus group of prominent people with him to his meeting with the CEO. Included in that group were people he had met during his time in the music industry including Run from Run DMC and Carl Banks from the New York Giants. One by one each member of this focus group stood and said they would definitely purchase a jet card if it was available. Itzler and his focus group were convincing enough for the CEO to give him and his jet card idea a shot.

Establishing credibility by selling to professional athletes and entertainers was their strategy for rapid growth.  Early on, Itzler (cunningly) put himself in a position to meet and pitch some pretty big names – Matt Damon, Ben Affleck and Jennifer Lopez. He knew if he could convince these three A-listers to become clients of Marquis Jets, he’d have all the credibility he needed for the company to take off. And it worked! Just one year after Marquis Jets was started it had already done $5 billion in cumulative sales and was even bigger than NetJets. Itzler and his partner sold the company to Warren Buffett.

The young Jesse Itzer may have used some pretty unconventional methods along the way, no one can argue that he hasn’t been wildly successful. Even if finagling your way to the top isn’t your thing, you can certainly take some of his lessons and apply them to your business.

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