Jesse Itzler’s Secrets of Success

The room stiffened: That’s not a motivational story! Yes, Itzler explained, it is: “My son chose to be a participant, despite not being great, rather than being a spectator. If you want to have an exceptional life, you have to put yourself in exceptional situations.”

What Itzler didn’t say was how devastating that dropped ball was. “It was so painful,” Sara Blakely told me. “Parents were crying, not just the children.” The ball field was on Itzler’s jogging route, so for more than a month he ran in the opposite direction. Three years later, he was still wistful: “Oh, if he just could have caught the ball—what it would have done for his self-esteem.”

Growing up, Itzler never had much to overcome. He was the youngest of four children in a Jewish family in Roslyn, a suburb of New York City, and a gregarious presence from an early age. “By the time Jesse was five, he was his own little rock star,” his sister, Janna, said. “At our local pool, he’d be schmoozing with the guy at the snack bar, saying hi to the tennis pros, then having lunch with the lifeguards, and everyone would be calling out, ‘Hey, Jess!’ It was already clear he was never going to have a desk job.”

Itzler’s mother, Elese, set the expectations: no swearing, no potholes on your report card, no Novocain for fillings. She told me that when he began travelling to breakdance, at fifteen, “it seemed very strange for someone of his age, race, and religion to be breakdancing on the streets of Washington, D.C.” Itzler’s father, Dan, was a tinkerer; he patented drains and faucets, but was proudest of his plans for a flying car. “My dad had a secret warehouse somewhere, like Doc in ‘Back to the Future,’ ” Itzler said. “He’d come home covered in an explosion of white paint, so all you could see was his eyes.”

After Itzler graduated from American University, in 1990, his mother urged law school, but his father let him pursue rapping. Itzler signed with Delicious Vinyl, then riding the fame of Tone Loc and Young MC, and recorded songs such as “Shake It (Like a White Girl)” (“She might’ve been snotty / But so what, the chick was a hottie”). Michael Ross, a co-founder of Delicious Vinyl, said, “I don’t know what we were thinking having a white guy singing ‘Shake it like a white girl.’ It was frat rap. It was good frat rap—but, to be honest, I’m not even sure that’s a thing.”

Itzler spent his twenties in music, and in 1997, when he was twenty-nine, he and a partner sold a sports-jingle company they’d founded, for sixteen million dollars. He then co-founded Marquis Jet, which offered the equivalent of time-shares in private aviation for a hundred and nine thousand dollars. His charm beguiled celebrities: he assured Jennifer Lopez that Marquis owned the six hundred planes that the company actually leased from NetJets. “It was just more convenient to say it that way,” he explains, adding that he quit hustling after NetJets purchased Marquis, in 2010. “In my twenties, I was working from a place of need,” he said. “If you told me it snowed, I’d say, ‘I shovel driveways!’ Now I’d say, ‘Here’s the number of the guy who does my driveway.’ ”

He and Blakely met in 2006, at a poker tournament hosted by NetJets. “I feel like our inner eight-year-olds fell in love first,” she told me. “That’s where we connected the deepest—at the ‘Oh, boy, this is so awesome!’ level.” They were well matched in curiosity, intensity, humor, and passion for human potential. Blakely’s parents separated when she was fifteen, and as her father left the house he gave her a six-cassette set of Wayne Dyer tapes, “How to Be a No-Limit Person.” She memorized them, and later visualized appearing on “Oprah” a decade before it happened.

Blakely had found that her success “emasculated my previous boyfriends a little. Some would lash out, and some would retreat,” she said. “So I was very nervous, three months before the wedding, when I told Jesse at dinner, ‘Honey, I have to tell you something. I think I make more money than you think I do.’ His eyes filled up a little, and he said, ‘Well, it couldn’t have happened to a better person’—and he went back to eating his spaghetti.”

The couple have strong Lucy-and-Desi energy, only Itzler is Lucy. In one of Blakely’s Instagram videos, she describes her extensive prep for a motivational talk they’re about to give together—hair, lashes, makeup, outfit. She turns the camera on Itzler, who holds up two T-shirts and asks, “Black shirt or blue shirt?” Blakely deadpans, “To be a man!”

Itzler’s inner eight-year-old still shapes his behavior. He hires young assistants, listens to youthful music, attends a basketball fantasy camp with men twenty years his junior. Their house, or at least his terrain within it, is like Tom Hanks’s apartment in “Big”: a boy’s dream of adulthood. There’s a mobile sauna in the driveway next to twin coolers for ice plunges, and inside there’s a basketball hoop and a climbing wall and a bubblegum machine and a painting that declares, “Everything Is Going to Be Fucking Amazing.”