But Itzler realized early on that one opportunity, if seized, can change everything. Years later, when he came up with the idea to start a private jet company, he knew he needed a single client to make it real.
So he showed up outside a TED conference in Silicon Valley and noticed a steady wave 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’ve got an extra muffin if you’d like one,” he’d offer to conference goers.
Itzler’s muffin bet could have easily flopped, leaving him with nothing but a pile of pastries and a bruised ego. But it didn’t, and that willingness to take smart risks, he said, is what often separates those who find purpose versus those who just show up for the paycheck.
“The best investment you can make in your 20s isn’t just a career,” he wrote. “It’s experience.”
And while that doesn’t mean you should recklessly call it quits on your career, he said young people should not be afraid to take a trip, try a side hustle, and say yes to an adventurous opportunity.
“Try everything,” he said. “Learn what sticks. Find what excites you. The time to explore is now.”
Fortune reached out to Itzler for further comment.
Having a bold attitude isn’t just a winning mindset, it’s a through line for many of today’s successful entrepreneurs.
Her scrappy approach didn’t stop there. Blakely rode around with a custom “SPANX” license plate, signed up for British billionaire Richard Branson’s reality TV show, and even paid her friends to go into department stores and buy her products so they wouldn’t be pulled from shelves.
Two decades later, the boldness paid off. In 2021, she sold the company for $1.2 billion—a 240,000x gain from her $5,000 investment. And because she opted to bet on herself throughout her journey, and never took outside investors, she reaped all the benefits.
Airbnb eventually landed a spot in Y Combinator’s startup program in 2008, awarding the company $20,000 in exchange for a 6% share—and the rest is history. Today, Airbnb is worth nearly $75 billion.
