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Life is a winding road. A lonely road, a dark and stony road, the road less travelled. Or, hang on, maybe life is a chrysalis, a labyrinth, or a box of chocolates. Whatever life is—and we have no fucking idea, really—we know that, to master it, we must first liken it to something we do understand.
Not so long ago, that analogizing was the work of shamans, imams, and ministers. Nowadays, it falls to muscular men in black jeans who prowl the stage: the motivational speakers. They know that each of us has a dream life, one that seems as distant as childhood happiness. They make getting to it a matter of discrete steps—believe in your greatness; envision where you want to be in a year; find the window in every wall—and urge you to start taking them. “Own your future—because if you don’t, someone else will!” they cry. “Everything you want is on the other side of ‘Yes!’ ”
The first challenge motivational speakers must overcome is that motivation galvanizes people for only about forty-five minutes. The second is banality: it is hardly an esoteric secret that it’s important to set clear goals, embrace opportunities, and persevere through rejection. The third is that “motivational speaker” smacks of quackery. So the motivators now call themselves “inspirational teachers” or “life strategists” or “global experts on human genius and personal transformation.” By transforming their own lives, at least, America’s twenty-five thousand life coaches and growth facilitators have helped make motivation a thirteen-billion-dollar industry.
One evening in June, two hundred and sixty people gathered in a ski lodge at the foot of Bald Mountain, in Sun Valley, Idaho. They had paid almost five thousand dollars to summit Mt. Everest, by analogy. At six o’clock the next morning, they would climb Baldy, take the chairlift down, and repeat, until, after fifteen ascents, they’d climbed 29,029 vertical feet—the elevation of Everest. A company called 29029 Everesting had organized the event and staffed it with inspiring coaches: a former Olympian who had recently completed seven marathons in seven days on seven continents; a triathlete known for competing with his brother, who has cerebral palsy, strapped to him. But the keynote speaker was a fifty-five-year-old self-described “back of the pack” triathlete named Jesse Itzler.
Itzler, who co-founded 29029 Everesting, is rangy and puckish, and he appears to have plucked his outfits from a college student’s laundry basket. His résumé is all hairpin turns: a former rapper, he wrote the earworm New York Knicks theme song, managed Run-DMC, and launched five successful companies, including a private-plane-rental service, before becoming a part owner of the Atlanta Hawks. Having found his métier in motivation, seven years ago, Itzler is determined to become its leading practitioner. He believes that what we really want is to feel proud of ourselves. His chief method for instilling pride is to set physical challenges so difficult that you must discover something new within yourself to meet them.
As Itzler held the mike in a nineties-rapper crouch, many in the audience seemed apprehensive about climbing the mountain that loomed outside. After ascertaining by a show of hands that half of those present had never even run a 5K, Itzler began with a story of overcoming. Overcoming is a staple of motivational speaking: I’m an ordinary person, like you, who overcame cancer/homelessness/getting bitten by a radioactive spider and achieved extraordinary results. Itzler said that his oldest son, Lazer, suffered from such severe anxiety about going to a new school that he wouldn’t get out of the car on the first day. “I said to Sara”—his wife, Sara Blakely, who founded the shapewear company Spanx—“ ‘He just has to make one friend.’ ”
Itzler didn’t recount the experience so much as relive it: pacing, doing the voices, his hand to his ear for the call with the principal, who told him that Lazer wanted to come home early. Itzler demurred, not wanting his son to take the easy way out, but said he’d be first in line to pick him up after school. The parents in the audience were listening intently. The principal called back at 2 p.m.: “ ‘Mr. Itzler, your son wanted me to tell you that he’ll take the bus home today.’ I said, ‘What happened?’ ” Itzler made eye contact around the room. “He said, ‘He made a friend.’ ”
As many in the crowd took a breath, seeming surprised by their emotion, Itzler pivoted to the immediate challenge: “Tomorrow, on the mountain, I guarantee there will be a moment when you can say something to someone else that will get them to the top. I guarantee that you can be a friend to one person, and you’ll feel better about yourself.” Having turned a roomful of strangers into a community, he then gave them a common enemy. (Itzler is a fervent believer in competition: after a recent colonoscopy, he asked the doctor, “Do I have the cleanest colon of anyone you’ve ever done?”) An opponent much larger than Bald Mountain was in view, he said. “Time is undefeated. The only way you can have a fistfight with time is to do things you’ve always wanted to do. Do something that lasts forever.” He thrust his right arm high, and the crowd rose. Tomorrow, he promised, “we are going to take this fist and shove it right up time’s ass!” Pandemonium.
In the morning, I climbed the mountain with Itzler. Beforehand, he’d seemed uncertain that his talk was durably inspirational. “Was it life-changing, or just moment-impacting?” he wondered. But as we made our way up what some hikers were calling “the Wall,” a section that rises eleven hundred feet in seven-tenths of a mile, his brio returned. “Everyone else is opening their e-mail at work right now, and we’re cruising up a mountain!” he said. I couldn’t even grunt back.
Three-quarters of the hikers would finish all fifteen laps. Adam Organ, a forty-seven-year-old with a Biblical beard, wasn’t among them. His climb was meant to crown a season of self-transformation. Pushing three hundred pounds during the pandemic, he had grown worried that he wouldn’t make it to his daughter’s college graduation, so he got a Peloton and sought out sources of uplift. On Bald Mountain, he sprained his knee on his seventh ascent. “It was, like, I’m on the Apollo 13 and failure is not an option,” he told me. “So I one-leg-climbed to the top of the Wall, and then I cheered other people on. I was crying a lot, but I was so glad I was there.” A few weeks later, Organ dropped out of another 29029 climb with altitude sickness. Undeterred, he e-mailed me, “I continue to come back to Jesse’s comment that if a goal doesn’t scare you, then it’s not big enough.” That mind-set “is changing how I view my life.”
Itzler told me, “What I’m really doing is providing people with a foundation for how to live. I could definitely make this a hundred-million-dollar business, because the category has exploded, and there’s such huge need.” Yet motivation, like intimacy, is hard to scale. It works best in high-school locker rooms, less well in arenas, and rarely, or barely, on Instagram. Itzler intends to grow with his clients—yet he worries that reaching the summit in his field might prove incompatible with becoming his best self. “This space is filled with a lot of people regurgitating what other people have been saying for years, a lot of predatory marketing, a lot of snake oil,” he said. “Everybody says they’re not in it for the money, but everybody’s in it for the money.”
The American experiment has always been defined by the pursuit of happiness. The accompanying caveat was that the pursuit wouldn’t be much fun (first, row across the icy Delaware River; next, endure a Valley Forge winter without shoes; etc.). As Benjamin Franklin reminded the readers of “Poor Richard’s Almanack,” “There are no gains, without pains.”
In suffering we trust. Yet we also venerate the Roomba and no-knead bread, the labor-saving hack. Wouldn’t transformation be easier without all the hardship? In “The 7 Habits of Highly Effective People,” Stephen R. Covey observed that, by the eighties, America had shifted from the Character Ethic of Franklinesque hard work to the Personality Ethic, defined by “quick-fix influence techniques, power strategies, communication skills, and positive attitudes.” Self-help books helped lower the bar: all you need is what you learned in kindergarten and a little chicken soup for the soul. These days, it’s enough just to absorb a Ted talk—say, Shawn Achor’s proposition that it’s not that hard work and success make you happy, it’s that happiness makes you hardworking and successful.
Self-help itself recently got an upgrade to “personal development.” It’s no longer the remedial training you undergo to quit smoking but a personal-brand refresh to catapult you into the C-suite. Every weekend, around the country, conferences attract aspirants eager to flip houses, or sell solar panels, or just get rich in some unspecified way. The conference-goers, mostly in their thirties and forties, have the air of commuters who missed the first train to the city and are determined to crowd onto the next one. They seek trade secrets and, better still, the mind-set to deploy them. Kent Clothier, who runs a conference called Scale and Escape, told me, “Whatever you’re doing—real estate or marketing or athletics—personal development is the foundation.”
In July, nine hundred seekers descended on the Resorts World hotel, in Las Vegas, for a real-estate conference called the Forward Event, where they were bombarded with messages like “If you want to increase your net worth, you have to increase your self-worth.” Dan Fleyshman, one of the speakers, sat down with me to explain the business model. Skinny and spectral, he made millions from such diverse enterprises as hoodies, baseball cards, and energy drinks. He now has a popular podcast, “The Money Mondays,” and hosts empowerment conferences such as Limitless Arena. Fleyshman described a pyramid of access, in which you upsell adherents and then sell them back down, keeping them continually engaged. “Start by selling something cheap—a paid newsletter, weekly coaching on Zoom,” he said. “Once you have their credit card, they’re in the funnel. Then you invite them to your conference and upsell into the V.I.P. and Super V.I.P. tickets.” People pay to be closer to the source of inspiration. A backstage pass might cost ten thousand dollars. A “mastermind” program—group-coaching sessions led by the motivator, often in an exotic locale—could be twenty-five thousand more. As Clothier told me, those who keep paying to get to the next level “are trying to compress time and go faster, the same way people pay more to get to the front of the line at Disney World.”
Top speakers on the conference circuit make between fifty and a hundred thousand dollars for a talk, with a handful nearer to four hundred thousand dollars. Oprah, who’s on her own planet, charges a minimum of a million. Nearly all motivators espouse taking risks, serving others, and being grateful, but the most successful offer ready-made fixes for impediments to change—the fear of failure or embarrassment, the inexorable claims of inertia. Fleyshman told me, “People want to learn how to do everything, which is why they come to these conferences—only it turns out they don’t want to do anything. That’s why so many pitches from the stage are ‘Done for you’—we’ll build your Web site, or run your S.E.O.” He shrugged. “If you put a dog in the back yard, it just starts digging holes unless you give it a purpose. We try to give people a purpose.”
There is a noticeable gap between the values that many speakers profess and the images that stud their introductory “walk-on” videos: Lamborghinis, mansions, cascading Benjamins. Brad Lea, who spoke at the Forward Event, said, “There are a lot of goons who tell you to do good, and as soon as they walk offstage they’re doing lines of coke and banging hookers.”
Grant Cardone, a former motivational speaker, told me that he gave it up when he finally faced the truth: he’d been a fraud. “The most successful people not only don’t need motivation, they don’t want it,” he said. “They want aspiration.” Cardone now runs the well-known 10X Growth Conference, whose promotional materials showcase his Gulfstream jet and his Rolls-Royce. “That whole thing of ‘I own nothing but I’m happy’—that’s one thousand per cent because those people couldn’t make the money,” he said. “Happy was their second choice.”
In an improvised greenroom near the conference-room stage at the Virgin Hotel in Nashville, Jesse Itzler blasted Phil Collins’s “In the Air Tonight” and strode around, silently rehearsing. He was about to speak to the sales team at Mozarc Medical, which, as he’d just learned, makes dialysis machines and catheters. “Big fan of your energy!” a Mozarc manager told him. “Hopefully you can make these guys run through a wall!” Itzler bobbed and grinned, knowing he was being paid fifty-five thousand dollars to electrify the audience in a corporation-specific way: not so much “follow your dream” as “stay the course.” He told me, “I’ve been told beforehand, ‘Make sure people don’t quit!’ ”
After being introduced, Itzler came on to the beat from “Rapper’s Delight,” laid in by his onstage d.j., Dee Wiz. Itzler hired Wiz two years ago to intensify his messages, and they rehearsed for weeks, down to the word. “I hate introductions,” Itzler began. He explained that, back in 1991, when he was a rapper known as Jesse Jaymes, he was booed so thunderously after being announced at a benefit concert that he tossed a few T-shirts into the crowd, to win them over. “And then I said, ‘Thank you very much, Salt-N-Pepa is up next!’ and I got the fuck out of there!” Dee Wiz played a snippet of Salt-N-Pepa’s “Push It,” and the audience laughed and relaxed.
Some speakers build an argument from PowerPoints; Itzler works like a comedian, assembling short bits into a routine. He suggests that you take a few minutes a day to send three texts or D.M.s to people who inspire you, planting a thousand seeds a year from which relationships can bloom; that you compliment, congratulate, and console those close to you; that you always go to the funeral. And he forcefully reminds you that, once you subtract the hours you spend working and sleeping and eating and watching Netflix, you have only a quarter of the year left to create memories.
Itzler told the salespeople that when he looked into retirement communities for his parents he discovered the acronym “SIPPS,” for the categories used to grade quality of life: “Social, Intellectual, Physical, Purposeful, and Spiritual.” He went on, “Nowhere in those criteria do they talk about Instagram followers, the watch you wear, the car you drive.” He spun, his voice rising. “Financial wasn’t even a category! Man, that’s a far cry from what I hear when I speak at conferences. People come onstage and say, ‘Do what I do and you, too, can be a billionaire!’ Really? There are seven hundred and fifty billionaires in the United States.”
There was only one in the room that afternoon: after Sara Blakely sold a majority stake in Spanx, two years ago, the couple’s net worth surpassed a billion dollars. Itzler wears his wealth lightly, but it validates him onstage; it gives him the authority to call wealth into question. “We often neglect this side” (he raised his right hand, representing values) “as we develop this” (he raised his left hand, representing financial success). “If you have a billion dollars, and your spirit is zero, a billion times zero is zero.” He said that his father, who ran a plumbing-supply house, was a devoted checkers player who never let Itzler beat him until a few years ago. “He was telling me, ‘Jesse, nothing’s going to come easy to you. Not even your own father is going to let you win. But if you work hard, even if it takes fifty-five years . . . you might get what you want.’ ” His voice growing husky, he observed that Dan Itzler never got rich, but he was “a spiritual billionaire.” In five minutes, Itzler had escalated from jaunty to heartfelt, and carried the audience with him.
For Itzler, success is not a solitary arrival at the peak but a collective willingness to embark on an uncertain voyage. He spoke about Lazer deciding to play baseball at age twelve, despite having no experience. (Itzler assured me, “I run anything I want to use by Lazer beforehand, and he feels like a superstar when he hears stories about himself.”) Where they live, in suburban Atlanta, Little League is serious business, and Lazer was the last kid drafted after tryouts. “I’m, like, We’re fucked,” Itzler said. “You’re either going to get radically bullied or you can be an exceptional teammate.” Lazer’s team parked him in left field and made it to the championship, despite his inability to hit or field. He was an exceptional teammate, though, and when he finally got a hit he was mobbed. The championship game, in Itzler’s telling, was a “Casey at the Bat” epic. It came down to a bases-loaded fly ball hit to Lazer: if he caught it, they won. But he dropped it.
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.”
As the couple had children, though, there was a gradual accommodation to adulthood. Blakely said, “When Lazer was three or four, I had us draw up columns of who does what, because the wheels were coming off. Jesse’s column was ‘Play with the kids.’ ” (Itzler sheepishly acknowledges, “I thought sneakers and doctors’ appointments just magically happened.”) “When he saw all that I was doing, he got tears in his eyes, and said, ‘Let’s go through your column, and I’ll do all the ones you feel comfortable having me do.’ ” She added, with a smile, “But it’s still an ongoing conversation we have twice a year!”
When Itzler was starting his career, motivational speakers were avuncular figures: bow-tied Zig Ziglar; folksy, pious Norman Vincent Peale. By the time he became a motivator, the industry had transformed, in tandem with its embodiment, the raspy, six-foot-seven, astonishingly confident Tony Robbins. Robbins began his work, forty-six years ago, by encouraging clients to walk barefoot across glowing coals. Anyone could do it if they moved briskly—coals are relatively poor conductors of heat—but it made you feel invincible. He now gets a minimum of five hundred thousand dollars to speak, and charges personal-coaching clients a million dollars a year, plus a cut of their profits. But he is best known for his events, such as the lavishly produced Unleash the Power Within, which promises “four days of completely rewiring your nervous system to attract overwhelming abundance in EVERY area of your life!”
Robbins popularized the belief that the mind follows where the body leads. In between his curative “interventions,” he has the audience jump and clap and sway and shout along, harmonizing their systems with his. “I burn eleven thousand three hundred calories a day onstage,” Robbins told me. “They measured my bone density and I’m stronger than 99.9 per cent of the population, and I have the lean body mass of a lineman. What happens in my body—and in the audience’s, because everything in their bodies matches mine, down to the heartbeats—is that testosterone surges through the roof. So now you’re so focussed that you retain whatever you’re learning.”
In the Robbins Era, the leading motivators tend to be former Division 1 decathletes or jujitsu black belts who post on Instagram about hitting the gym at 4:32 a.m. Workouts increase discipline and energy, produce measurable improvements, and make you look ripped. Fitness also lends itself powerfully to analogy. Heavy weights aren’t a burden; they’re a way to get stronger.
Itzler has no patience for motivators whose message is “Be young and buff like me.” He says he wouldn’t have had anything to tell people before he’d had failures and successes as an entrepreneur; before he got married and had kids; before he built a repository of wisdom. Yet his obsession with fitness led him into the field, and it defines his brand.
He first saw David Goggins, a retired Navy SEAL, at a twenty-four-hour relay race in 2005. Itzler was part of a five-man team; Goggins was running alone, fuelled only by protein powder and a box of crackers. They stayed in touch, and in 2010 Itzler invited Goggins to live with his family for a month and train him. Blakely said, “You know how, in fourth grade, you’d write someone a note saying, ‘Do you want to be my friend? Check the box, yes or no’? Jesse is still doing that.”
Goggins, who later set the world record for consecutive pullups, believes we are driven by anger and fear. His motto is “Stay hard!” and he views men as either savages or pussies. “Some of you are so weak,” he observes, in one of his videos, “just being in your very presence can make a man go impotent.” He trained Itzler by waking him at 4 a.m., with a whispered, “Get up, motherfucker,” to do pullups to exhaustion or run ten miles or plunge into a freezing lake. By the end of the month, as Goggins had predicted, Itzler could do a thousand pushups in a day.
In 2015, Itzler published a book about the experience, “Living with a SEAL: 31 Days Training with the Toughest Man on the Planet,” which became a Times best-seller. Afterward, an old friend in finance asked Itzler to share what he’d learned with his sales team. Itzler discovered that he could inspire people—and that it made him proud. Within three years, he was at Marlins Park, in Miami, speaking to thirty-six thousand people.
“Living with a SEAL” doesn’t mention that Goggins stayed with the Itzlers, on and off, for six years. In 2017, the two men had a falling out that left Itzler “disappointed on where we ended up after so many years.” (He wouldn’t go into specifics, and Goggins declined to speak to me.) Chris Hauth, a former Olympic swimmer who is Itzler’s “mind-set coach,” said that, for Itzler, training with Goggins “was the defibrillator paddles that shocked him so completely, they flipped him upside down. But I think he saw that anger and fear and constant yelling is not who he really is.”
To many rudderless men who feel at sea, toxic masculinity seems like a safe harbor. Ed Mylett, a prominent speaker, told me, “The easiest lane to get big right now is right-wing politics and hypermasculinity. Show ’em your Lambo, show ’em your mansion, show ’em your muscles, and scream at ’em.” Though seventy-five per cent of the life coaches in North America are female, women are vastly underrepresented among the best-paid motivators. Of the seven speakers on the poster for the Forward Event, six were men. “I am so often the token female at these dude events,” Jen Gottlieb, a podcaster and speaker, told me.
Itzler’s masculinity is relatively evolved, but he does dwell on grievances. When a lone detractor called him “pampered” in a reply to Itzler’s Instagram post about an Ultraman (perhaps because he’d brought a team of six to film, hydrate, and Theragun him), Itzler groused about it for weeks: “I will never forget that!” But he generally uses grudges as fuel for the next race, then discards them like an empty bottle of Muscle Milk. “Something must have happened in my childhood where I thought I had something to prove,” he told me. “I’d have to spend a lot of time on the couch to figure it out.” Any plans to? “Nope!”
In 2019, Itzler sought out another ex-Navy-SEAL ultramarathoner, Chadd Wright. A staple of Itzler’s current speech is the weekend Wright spent at Itzler’s house, counselling him about gratitude and about never acknowledging distress when you hit the wall: “The only answer to ‘How do you feel?’ is ‘Outstanding!’ ” Wright told me, “Hate and anger fuelled me for eight years as a SEAL, but they’re dirty fuel. Cleaner fuels—like love, joy, the power of the spoken word—propel you much farther.” Itzler explained, “David is ‘Stay hard’ and Chadd is ‘Be hard when it gets hard.’ Both are super motivators. But it’s hard to always be hard, especially when you have kids.”
Itzler’s maxim is “I’m never too tired for my kids.” He once flew home from New York to watch Lazer in a twenty-two-second breaststroke race, then flew back. His friend Chris Paul, the N.B.A. star, told me, “Half the time we talk, it’s just about parenting.” Itzler’s children—he and Blakely have four—also provide much of his material. After a typical day at home, he told one audience, “Fifteen lessons happened to me in twenty-four hours!”
In July, I visited Itzler and his family at their summer house, in New Fairfield, Connecticut, on the shore of Candlewood Lake. It was two days before his annual Hell on the Hill fund-raiser: a hundred and ten people would attempt to run up and down his nearly vertical back yard a hundred times, and Itzler and Blakely would donate a thousand dollars to each person’s charity. Thirty participants who’d come early were in the yard, cheering Itzler on as he hurled cherry tomatoes from the garden at Devon Levesque, his co-founder in an events-and-sports-gear company called All Day Running. Levesque caught every tomato in his mouth, like a trained seal. “Go deeper!” Itzler said, waving him away. “Deeper!”
Itzler turns nearly everything into a game, a contest, a chance to measure yourself. He and Blakely agree that if one of their children says, “I can’t,” they reply, “Itzlers don’t say that.” Yet when he took the kids out on a pontoon boat, half an hour later—after making sure they introduced themselves to me with strong handshakes—he declined their pleas to jump off Chicken Rock, a thirty-foot-tall boulder overlooking the lake. “I’m a scaredy-cat,” he serenely explained. He avoids high leaps, high speeds, or any situation involving sharks. He focusses on trials of the spirit, where he can apply what he calls “my superpower of goal endurance.”
The popular sell in motivation is instant transformation—one weird trick to get rich!—but Itzler’s program is based on plodding through dozens of small steps. He told me, “When Tony”—Robbins—“has people walk on hot coals, the similarities with what I do are ‘Getting over the fear’ and ‘Doing it in a group’ and ‘Wow, I didn’t know I could do that.’ But hot coals lasts, like, three seconds, and everyone can do it. After the first three seconds of 29029, you’re not even .00001 per cent of the way to the end.” Robbins believes that emotional pain pushes people to the threshold of change; Itzler sees it as a signal to redouble your efforts. Onstage, he likes to say, “I willed my way to where I am in life by sheer wanting. I outwanted people.”
For Itzler, the power of mind-set is a sacrament. He insists that, in the right frame of mind, he could outrun his friend LeBron James in a hundred-mile race. “LeBron, Kobe, Michael Jordan—I’d beat them all at their peak,” he told me. “One, I want it way more than any pro athlete would. What do they have to gain by going through all that suffering to beat a fifty-five-year-old guy? And, two, the hundred-miler comes down to will. It’s the entrepreneur’s journey.” (Chris Paul said, dryly, “The mental aspect of it is huge, but if LeBron trained? He would beat Jesse.”)
That evening, Itzler sat on his screened porch to enjoy an incoming storm, grinning at each flash of lightning. Others gathered around, including Chris Hauth and another Olympic swimmer named Katie Hoff, and soon Itzler was eying the lake, which was a third of a mile wide. Within minutes, a contest had developed: could the Olympians swim a relay back and forth across the lake before Itzler and two of his back-of-the-pack friends made it across? There was a lot of discussion of currents and sight lines and pace and drag, until Itzler finally said, “This whole deal comes down to one thing and one thing only—”
Hoff solemnly completed the truism: “—the will to win.”
“—math,” Itzler said. “I know how long it takes to swim across the lake.”
The following morning, dozens of people gathered on pontoon boats to watch. As Hauth shook his legs out, nervously, he said, “This is what Jesse does—create ridiculously fun events out of nothing!” Itzler was right about the math: the Olympians didn’t come close to making up the handicap. But he said later that what mattered most to him was what the competition inspired: his seven-year-old daughter, Tepper, “swam across the lake for the first time, and Charlie and Lincoln”—his nine-year-old twins—“swam across and back! Big ripple effect!”
His home is an incubator for optimization. Itzler recently told an audience, “I said to my brother about my son, ‘He’s a good swimmer, but he doesn’t really have that eye of the tiger,’ and my brother said, ‘That’s O.K., as long as he’s happy.’ ” There were murmurs of approval. “And I’m, like, ‘No! He’d be happy playing Fortnite and eating Häagen-Dazs every night. We want him to live up to his potential.’ ”
Itzler has a parental knack for infusing you with his intentions. You simply take it on faith that those intentions will behoove you. Late one afternoon, as he and I flew through Atlanta on the way to his next talk, we ran between terminals to catch a connecting flight. The T.S.A. line was long, the plane would depart in nineteen minutes, and Itzler clearly wanted to turn around and go have dinner with his kids. “What do you think?” he said. “Sauna and a cold plunge waiting!” He studied me. We’d have to get up at 5 a.m. to make our rescheduled flight, but I didn’t want to disappoint him. “Let’s go tomorrow,” I said. “Great decision, Tad,” he said, grinning. “Great decision!”
Motivators, like parents, don’t so much instruct you as remind you of good habits. Yet, if you ask ten motivators which habits are effective, you’ll get twenty ideas. Lewis Howes, who has interviewed more than a thousand leaders in personal development on his podcast, “School of Greatness,” asks each one for “three truths.” Howes told me, “My takeaway is that it comes down to ‘Love a lot. Love people, love life, love yourself.’ ” But if people were able to do all that, unprompted, they wouldn’t need the conference at the Marriott.
The consensus in the field, to the extent that there is one, is that to create new habits you need motivation plus mind-set plus a methodology. Itzler believes the best way to start that process is by “building your life résumé.” He asks followers to fill out a wall-size “Big A## Calendar,” which he sells for forty-seven dollars. Schedule in mini-adventures every two months, build a winning habit (such as cutting out added sugar) every quarter, and, most important, frame your year around a misogi. In Japanese, the word describes a purification ritual, but in Itzler’s parlance a misogi is a daunting challenge that forces growth. A marathon is too easy: almost everyone who trains can complete one. A fitting misogi could be skydiving to conquer your fear of heights, completing a triathlon, or repairing a relationship with an estranged parent.
Itzler began setting life goals in his mid-twenties: be a millionaire by thirty; have a song in a movie; run a marathon (check, check, check). He asked successful people for their most powerful habits and began eating only fruit before noon and spending three hours a day on his own development. When he doesn’t understand something, such as how to read a complex balance sheet, “I feel super small—versus any other area, where I feel super big,” he said. At fifty, he drafted a list of skills to acquire, and he’s since hired experts to teach him how to improve his memory, decipher body language, ride a motorcycle, free dive, and perform C.P.R. “It’s like the ‘Bourne’ movies, where Jason Bourne knows all the languages, spy tricks, how to fight,” he said. “The more I can layer into my toolbox, the more unstoppable I become. And the by-product is separation from everybody else in my space.”
He studies other speakers, constantly comparing, tweaking, seeking to improve. He told me, “I want to make someone feel bad they came before me and terrible they went after me.” His peers are no less competitive. The motivator Erwin McManus told me, “I was in a room full of great speakers recently, and they were all asking each other, ‘Who’s the greatest communicator in the world?’ I said, ‘Maybe the question should instead be “What do people most need to hear?” ’ ” McManus, who coaches other speakers, rates his clients on a personality test called the Birkman Method. “They’re all in the nineties out of a hundred, where the higher the number, the more you’re affected by how other people perceive you,” he said. “They all have a deep conviction that their message is the most important one. And that message, so often, is ‘Don’t care what other people think about you.’ ”
Itzler disparages the measures of success in his industry—griping that you have to pay up to ten thousand dollars to be included on certain lists of top coaches, and that numerous colleagues “claim they have the top-rated podcast or bring in a hundred million dollars—all this uncheckable hype!” But he still wants to reach the top. Once, when we were discussing his coaching program, he laughed and said, “The bitterness you hear is that I haven’t been able to crack the code and get to a higher level.”
He launches new offerings by following his gut. “Four years ago, Jesse asked me, ‘Do you want to be a coach for my calendar club?’ ” Laurie Wintonick, who now runs his coaching programs, told me. “I said, ‘What does it entail?’ And Jesse said, ‘I have no idea.’ He’s totally ready, fire, aim.”
When Itzler and Wintonick met recently to discuss revamping their programs for next year, Itzler declared, “This industry is built on predatory advertising that tells you your life is broken. ‘If you feel you haven’t lived up to your potential’—which is everyone!—‘the only way to achieve that is to take my ninety-nine-dollar program, and I’ll teach you how to get a private jet.’ To promise someone a free Webinar, and then bombard them with e-mails for all these other products, that’s horseshit—”
Wintonick interrupted to point out that their media team sends a flood of e-mails, too. Itzler looked stricken. “ ‘If you like that, we also have this’ is completely different from ‘We’re offering this free Webinar only so we can upsell you into our nine-hundred-and-ninety-seven-dollar program,’ ” he protested.
Whatever conventional wisdom recommends, Itzler is inclined to reject; one of his Webinars is called “Normal Is Broken” (normal, he points out, is overweight, divorced, and depressed). Yet, in his efforts at outreach, he often finds himself on well-trodden ground. He has spoken at five Tony Robbins events. He has a full-time staffer who shoots video of him and posts clips on YouTube, TikTok, and Instagram. And he currently has an online calendar club ($1,000); the Elite365 program, which provides coaching in such categories as business, nutrition, intermittent fasting, parenting, and mind-set, as well as quarterly calls and two retreats with Itzler ($35,000); and the Premier365 program, which offers even more coaching and face time ($75,000).
Robbins doesn’t believe that his industry needs an overhaul. “I love Jesse to death,” he told me, “but it’s unrealistic to think we’re going to make people do something he wants in a world where they have free choice. The best will rise to the top and the weakest will fall to the bottom.”
The clients of Itzler’s I spoke to are also satisfied with the status quo; his retention rate is about seventy per cent, well above the industry norm. Stephen Odom, a C.E.O. who’s in Premier365, told me, “How do you put a value on me calling my dad from Jesse’s house and telling him I loved him and why he’s such a great dad, and having him tell me that nothing I could ever have said would be worth more than that? Between myself and my company, I’ve probably spent close to a million dollars on Jesse, and I will spend more.” Another of Itzler’s devotees, Risa Kostis, a stylist and personal shopper, has been in his calendar club for three years. She’d love to level up, but his masterminds aren’t cheap. “I pick up a lot from Jesse’s Instagram,” Kostis said. “It’s like Taylor Swift fans listening to her from the parking lot because they can’t afford a ticket.”
Itzler knows that his value rises with proximity, as the experience nears personal coaching. He’s particularly excited about next year’s quarterly “SweatLodge Retreats” at a five-hundred-acre property he owns in northern Georgia, where people can spend three days with him meditating, hiking, biking, taking sound baths and saunas, and chilling out. “It’s loosey-goosey!” he told Wintonick. “I can do a fireside chat at night—we should add that—or get in the sauna with people. That’s where I shine, where I make them feel they can do more.”
Yet he also understands that the real money lies in galvanizing thousands of people at once. He went on to lay out a plan of ten Webinars, to stock a digital library that will allow him “to earn while I sleep.” Then he pivoted to an even more commercial idea: “Jesse Itzler Live,” a speaking tour to establish him nationwide. “We’d start at the Beacon in New York. Off Broadway theatre, or comedy room, that kind of vibe, intimate. It’s forty-nine dollars to get in, up to five hundred dollars for V.I.P. with an after-party. Day two, we offer everyone a run and then smoothie bowls, cold plunge, sauna, and a two-hour immersion course, where I’ll have some kind of curriculum, and that could be a thousand or fifteen hundred dollars additional. Year two, I’d change the speech and hopefully triple the size of the venues.” He nodded, visualizing. “Year three, arenas.”
Google plans to introduce an A.I. life coach, but its experts recently cautioned that users could experience “diminished health and well-being” and “loss of agency” if they took advice from an algorithm. We need the personal touch. That need used to be met at houses of worship. Erwin McManus, who’s also a pastor, told me, “This space has exploded with the loss of faith in organized religion. You can’t look at optimizing human potential and not feel it as a deeply spiritual calling.”
The motivational experience mirrors going to church—the catechistic phrases, the stand-and-testify choreography, the joy of gathering with fellow-believers. Only the focus is different: this life, not the next. “People see an actual church coming a mile away,” Ed Mylett, who makes no secret of his Christianity, said. “People come to see me, a muscular dude with an island and a jet, because they think they’re going to get that recipe. I can reach them because of my worldly success, but I tell them, ‘You don’t want the jet, the island, the muscles—you want how you think you’d feel if you had it.’ ”
For his part, Itzler is uncertain how much spirituality is required to become a spiritual billionaire. “I’m starting to evolve into that, the deeper questions,” he said, “but for now I just dummy it down to ‘Do unto others.’ ” Even as he encourages people to pattern their lives on his, he fears the responsibility of becoming a role model. Two people in his program have asked him to bail them out of jail, and others have sought his counsel because they’re contemplating divorce, or suicide. “I’m a pleaser, I get energy from people, I’m not a therapist,” he told me, his eyes wide with alarm.
Where therapy leads to self-knowledge, and religion offers grace, motivation valorizes success. Its foundational premise is that life has a secret plan for you, and the motivator has acquired a copy. Dean Graziosi, who leads programs with Tony Robbins, recently said in a video aimed at potential enrollees, “If you’ve got the blueprint, and you keep trying, isn’t it a fact that you will succeed?”
In this reassuring view, setbacks don’t happen to you, they happen for you, so you can grow. But, if persistence guarantees success, then when you fail it’s entirely on you. You flunked life. This belief has powerful social consequences: governments and companies have no duty of care, because everyone should take care of himself. Zig Ziglar once told A.T. & T. employees facing a round of layoffs, “Don’t blame the boss—work harder and pray more.” This belief also has implications for family dynamics. Mylett warns audiences that, if you don’t become a superlative provider, you’re telling your family, “I was more scared than I loved you.”
Itzler is remarkably free of fear. He occasionally wakes at 3 a.m. worrying about his mother, or his children—yet his confidence in his own luck defends him against vulnerability. “It’s hard to get Jesse to explain the deeper meaning of all this, even to a close friend,” his childhood schoolmate Kenny Reisman said, at Hell on the Hill. “Maybe it’s the Mrs. Itz in him, the stoic underneath.” The promise of motivation is, If I do exactly what you do, I’ll be you. But what Itzler’s clients hope to emulate may simply be the charisma he was born with.
Blakely told me, “As his wife, I would like to have conversations about feelings with Jesse. For years, I’d say, ‘How do you feel?’ and he would say, ‘I don’t know,’ and I’d get mad. And one day I realized, He doesn’t know. I gradually discovered that he could write his deeper feelings to me, or talk about them if we went on a walk together—he’s so much better in motion. I’ve thought about this issue a lot, having been with him for sixteen years, and I feel like he’s just happy.”
At the Forward Event in Las Vegas, Itzler shadowboxed backstage, preparing to deliver the closing speech. Brad Lea, who’d spoken earlier, told me he envied Itzler’s work ethic. “Jesse has it all worked out, and I just wing it,” he said. “I should fucking prepare, obviously, spend six months practicing and take over the whole fucking industry—become the king!—but I don’t, because why? I guess because I have a deep fear of trying, and fucking up, and looking ridiculous.” He laughed, surprised. “Because I’m normal, a normal human being.”
The event’s host, Neel Dhingra, introduced Itzler, who strode onstage, remarked that he hated introductions, then tore into his talk. Toward the end of his time, he said, “Nothing has had a bigger impact on me, my business, my family, and my children than what I’m about to share with you right now.” He told how Chadd Wright, running alongside him in a hundred-mile race, disclosed a secret at mile 74, when Itzler was broken and about to drop out. Wright said, “I never get tired!” That wasn’t the secret, though; the secret was broadcasting that belief. He urged Itzler to announce it to the woman at the next aid station. Too tired to protest, Itzler did—and Wright yanked him back onto the course.
“Mile 75, how do you feel?” Itzler cried, in Wright’s Georgia drawl. “ ‘I feel outstanding!’ Eighty, eighty-one miles through the dark, me and Chadd, no one around.” A photo of Itzler and Wright flashed onscreen, their headlamps piercing the darkness. “Ninety, ninety-one miles!” Dee Wiz was playing the tolling bells of “Going the Distance,” from “Rocky.” “All the way to the finish line of a hundred-mile race!” His voice rose: “The words that you speak matter! What did my son say? He said, ‘I can’t, I can’t get out of the car!’ ‘We don’t come from money!’ ‘I don’t have enough experience!’ ‘I’m not good at sales!’ The words that you speak matter! How do you feel?” He held his mike out:
“Outstanding!”
“Get up! How do you feel?”
“Outstanding!”
He repeated his question again and again, nine times in all: “How . . . do . . . you . . . feel ?”
“OUTSTANDING!”
Dee Wiz sampled an air horn. It was the obvious climax—yet Itzler continued, in a bedtime-story voice, “Now, listen, we’ve covered a lot.” He recapped his topics, from SIPPS to acting with urgency. “I told you guys I beat my dad at checkers, right? What I didn’t tell you is that when I beat my father he had no idea who I was.” We saw a photo of Itzler holding a sign that said “I am your son, Jesse,” as he explained that Dan Itzler had Alzheimer’s. “One of the last times I was at my parents’ house, I’m sitting in a chair and my dad turns to me out of nowhere and says, ‘Jess, son, do you want to play checkers?’ I was, like, ‘Yes, Dad—absolutely I want to play checkers!’ ” He went on, “Not everybody is going to have this”—left hand—“but, shit, everybody in this room can master this”—right.
That seemed like the end, for sure. Dee Wiz said, “Ladies and gentlemen, give it up—Jesse Itzler!” But Itzler quieted the applause to show a video of him in the I.C.U., not long before his father died, putting his phone to his father’s ear and playing “The Battle Hymn of the Republic,” a favorite of his. “Time is going to take everything away from you,” he said. “But—I mean this wholeheartedly—it can’t take away what’s in your soul.” Onscreen, Dan Itzler smiled and began tapping his foot, a light flickering on in a nearly abandoned house. Dee Wiz cut the hymn, but the audience kept singing: “His truth is marching on. . . .”
As the crowd filtered out, still buzzing, Brad Lea and half a dozen other speakers mobbed Itzler backstage. Keven Stirdivant, who’d spoken before him, said, “I’ve been going to these things since I was fifteen, and that was the greatest speech I’ve ever seen!”
Neel Dhingra would later tell me that Itzler had been superb, the highest-rated speaker, and that Dhingra had filled every slot in his mastermind. And yet, he went on, the ultimate success of the conference depended on your perspective: “You can think, Ninety per cent of the room got inspired—and then did nothing with it. Or you can think, It’s all a funnel, and to change a few lives you have to go through all the people you’re going to lose along the way.”
Afterward, Itzler sat in the empty ballroom as the hotel’s events team stacked the chairs. He was tired but radiant. A few parts of his talk needed tightening, he said, but in a year he’d have a totally different talk, and then he wanted everyone in the world to respond to him the way that Keven Stirdivant had. But what he also wanted—no, what he really wanted—was simply to inspire fellow-enthusiasts. “The move-the-needle is not ‘I want to be Jesse, or Ed, or Tony,’ it’s ‘I want to be like that,’ ” he explained. “ ‘I want to treat my customers differently, I want to never quit, I want to use this feeling to become better.’ That energy is my program. I breathe belief into people so they can win life.” I asked how you’d know you’d won, and he paused for a moment. Then he grinned and said, “I was thinking, I’m going to win the funeral contest—I’m going to have the most people at my funeral!” The workers drew back the curtains, and the desert sun poured in. “Thousands, I’m pretty confident! What an amazing R.O.I. on life!” ♦
