One of the major highlights of the 2022 Make BIG Happen Summit in Miami Beach was hearing from Jesse Itzler. Jesse’s eclectic career includes rapping, managing Run-DMC, writing the New York Knicks’ theme song, co-founding Marquis Jet and selling it to Warren Buffet’s Berkshire Hathaway, co-owning the NBA’s Atlanta Hawks, writing books about living with a Navy SEAL and Russian Orthodox monks, and founding All Day Running Co.
Jesse is also the only speaker we’ve had at our Summit who brings his own personal DJ!
But it wasn’t just Jesse’s variety of personal and professional experience and his incredible energy that inspired our Make BIG Happen Summit attendees. It was the values and purpose he shared while discussing all the things that money can’t buy.
Here are five keys from Jesse’s entrepreneurial journey to becoming a “spiritual billionaire.”
1. “Disappointment’s an important part of life.”
Jesse acknowledges the great luck he had to grow up with a billionaire father (not the kind of billionaire you’re thinking of–more on that in a moment). But he says, at heart, his father was a simple man who considered his family his true wealth. And despite the resources available to him, he never sheltered Jesse from experiencing disappointments of all sizes.
“My dad was the checker champ of Brooklyn when I was four years old,” Jesse says. “When I was seven, I was pretty good at checkers. My dad would annihilate me. He never let me win, ever. My dad allowed me to experience disappointment. He kept me hungry. He told me through checkers that nobody, not even your own father, is gonna hand you anything. Nothing’s gonna be given to you. You’re gonna have to earn it, even if it takes 54 years. And as I became an entrepreneur, those lessons kept me hungry. They became important to my journey.”
2. “Attract luck.”
That journey started with a string of failures and odd jobs … until Jesse rode on a private jet for the first time. He put all the lessons about grit and determination his father had taught him to work, including hoarding muffins outside of a TED conference so hungry — and wealthy — attendees would have to talk to him. That’s how Jesse met entrepreneur Josh Kopelman and Marquis Jet made its first sale.
“In four months, I went from kiddie pool attendant to co-owning a company that did $5 billion in sales,” Jesse says. “That’s not a story about me being a great salesman. I’m back-of-the-pack when it comes to sales. That’s a story of me putting myself in a situation where I can attract luck. Luck doesn’t happen Sunday night watching the Kardashians on your couch. Luck happens when you put yourself out there in an environment where the universe can reward you for putting yourself there. And then you have to take advantage of it.”
3. “Relationships can’t be transactional.”
As Jesse built up Marquis Jet, he gave his clients the kind of world-class service that they expected.
And then he went further.
Jesse explains, “I always tell my employees, if nobody taught you how to do your job, how would you do it if you ripped up the industry playbook? How would you retain your customers? How would you talk to them? So when Kopelman went to Mexico, I gave him a list of pediatricians in case there was an emergency with his kids. I made reservations at every hot restaurant at eight o’clock for two in case he and his wife wanted to go to dinner.”
Jesse also built his business relationships with the same three habits he uses with the people in his personal inner circle: Compliment, Congratulate, Console. When you’re there for other people in your business and your life, that goodwill tends to boomerang back when you need it the most. For Jesse, that included reaching out to his friend and fellow coconut water enthusiast, Matt Damon, to film a promo for Zico that helped seal a sale to Coca-Cola.
“Relationships can’t be transactional,” Jesse says. “They have to be deep, authentic, and meaningful. When you do that and you open up that side of business, the floodgates open. You need to pour your soul into things. Have deep, authentic, meaningful relationships with people.”
4. “Listen to the words that you speak.”
The Last Man is an endurance race where runners have one hour to complete a 4.2-mile loop. Finish in under an hour, and you get a timed break before the next loop starts. Eventually, one runner outlasts the rest.
Jesse did 10 training runs and couldn’t get past 38 miles. Impressive, sure, but not enough to go very far in The Last Man. So Jesse called up Chadd Wright, a runner and former Navy SEAL, for tips on how to break through that barrier. Chadd taught Jesse a three-part mindset hack that Jesse says transformed his life:
- Never give pain a voice. “If I ask you how you feel today, your only response is, ‘Outstanding!’”
- Never die in the chair. “Take quitting off the table. Either you exhaust every resource and you don’t complete your mission, or you’re successful. Success or failure are OK if you empty the tank.”
- Express gratitude. At the beginning of every loop in his run, Jesse said something he was grateful for rather than dwelling on how hard the race was.
Take a moment to think about how much of your daily inner monologue is wasted on negativity: worry, insecurity, self-doubt. Think about the tone of your interaction with employees, especially when someone makes a mistake. Think about the words you use when you and your spouse aren’t on the same page, or when your children are struggling.
And then, think about how you can rewrite all that dialogue to empower and inspire both yourself and those around you.
5. “Don’t give up what you have chasing what you want.”
Years after he built himself into a successful entrepreneur, Jesse finally beat his dad at checkers. But he was suffering from Alzheimer’s, and experiencing fleeting moments of clarity. When the end finally came, Jesse took some solace from knowing that he never passed up an opportunity to create a meaningful moment with his father, and that he had poured his soul into that relationship.
Do the same for your family, your friends, your employees, and your customers, and you’ll Make BIG Happen every single day.
“If you have a billion dollars and your soul is worth zero, a billion times zero is zero,” Jesse says. “But if you have $1 and your spirit’s worth a billion, a dollar times a billion is a billion. My dad was a spiritual billionaire. He had character, compassion, generosity, and kindness to all. So while not everybody is gonna wax rich on this side, everybody can still become a spiritual billionaire because those are attitudes that everybody has.”