In the current unstable job market and persistent inflation, leaving a dead-end job may seem impossible. The dream of doing something meaningful—or even something better—can start to fade, a feeling Jesse Itzler knows well.
Long before he became a multimillionaire serial entrepreneur, Itzler was cleaning refrigerated trucks in the US for $7 an hour and working summers as a paddling pool attendant. He even tried, unsuccessfully, to be a rapper.
But Itzler realized early on that one opportunity, if seized, could change everything. Years later, when he had the idea to found a private jet company, he knew he needed a single client to make it a reality.
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The Muffin Bet and the Reward of Action
He then showed up at the door of a TED conference in Silicon Valley and noticed a steady stream of attendees stopping by the local coffee shop. The next morning, he was there at 5 a.m.—and bought every muffin in the place.
“Hey, I have an extra muffin if you want it,” he offered conference attendees.
The small but bold act helped him make the right contacts, land his first customers and ultimately expand Marquis Jet to more than US$5 billion (R$26.7 billion) in sales. He sold the company to Warren Buffett’s Berkshire Hathaway in 2010 for an undisclosed amount.
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“Sometimes you’re just one move away from changing your life,” Itzler wrote on his LinkedIn earlier this year. “Not a business plan. Not an investor. A creative idea. A right conversation. A bold move. The universe doesn’t reward perfect plans. It rewards action.”
And while he admits that not everyone can build a multibillion-dollar business, the distance between where you are today and what you could be is smaller than it seems: “Stay consistent and take one small step every day.”
Itzler’s message to Gen Z: forget the ‘safe path’
Itzler’s muffin gamble could easily have been a failure, leaving him with just a pile of candy and a bruised ego. But it wasn’t, and that willingness to take smart risks, he said, is what often separates those who find purpose from those who just show up for the paycheck.
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“Right out of college, I watched friends dive head first into the job market,” Itzler recalled in a LinkedIn post last week. “Work, work, work. No travel. No experiments. No exploration. Just the grind. And before they knew it they grew old fast.”
Now in her early 50s, Itzler said she’s seen too many people take the so-called “safe” path—the steady job, the predictable promotion—only to find themselves stuck and burned out. Her advice, especially for Gen Z, is to resist what seems easy.
“The best investment you can make in your early 20s is not just a career,” he wrote. “It’s the experience.”
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And while that doesn’t mean you should recklessly abandon your career, he said young people shouldn’t be afraid to take a trip, try a side hustle and embrace an adventurous opportunity.
“Try everything,” he said. “Find what works. Find what excites you. The time to explore is now.”
“Fortune” reached out to Itzler for further comment.
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Fortune favors the bold
Having a bold attitude isn’t just a winning mindset, it’s a common thread for many of today’s successful entrepreneurs.
Take, for example, Itzler’s own wife, Sara Blakely.
The founder of Spanx used all her savings of US$5,000 (R$26,700), made by selling fax machines door to door, to launch her shapewear empire.
But, to get off the ground in the first few days, she needed to think outside the box, and even break some rules. When Blakely’s product arrived at Neiman Marcus department stores, she personally rearranged the displays, moving Spanx from what she called “the sleepiest corner of the store” to the checkout counter.
“I always say: ask for forgiveness, not permission,” she recalled to the School of Hard Knocks social media account.
His creative and aggressive approach didn’t stop there. Blakely drove a personalized “SPANX” license plate, signed up for British billionaire Richard Branson’s reality show and even paid friends to go into department stores and buy his products so they wouldn’t be pulled from the shelves.
Two decades later, the boldness paid off. In 2021, she sold the company for US$1.2 billion (R$6.4 billion) — a 240,000-fold gain on her US$5,000 investment. And because she chose to bet on herself throughout the journey and never accepted outside investors, she reaped all the benefits.
Brian Chesky, co-founder and CEO of Airbnb, shared a similar mindset of being willing to take unconventional risks.
In the company’s early days, Chesky and his co-founders struggled to attract investors to their untested idea of getting strangers to open their homes to travelers.
To stand out and fund its operating costs, the team designed and sold limited-edition cereal boxes called Obama O’s and Cap’n McCain’s during the 2008 presidential election.
The move paid off. Not only did it help them raise $30,000, but it also caught the attention of Y Combinator investor Paul Graham.
“Well, if you can convince people to pay $40 for $4 boxes of cereal, maybe, just maybe, you can convince strangers to move in together,” Graham said, according to Chesky.
Airbnb finally won a spot in Y Combinator’s startup program in 2008, which awarded the company $20,000 in exchange for a 6% stake—and the rest is history. Today, Airbnb is worth almost US$75 billion (R$401 billion).
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