There are many stories of people whose risks led to serious losses, but for the five individuals we focus on in this article, their gambles led to substantial successes. They made calculated yet risky moves and wound up millionaires—and in a couple of cases, billionaires. These are the stories that put them in the fast lane to fortune.
Betting the Business: Entrepreneurs Who Went All In
Business can be a significant risk, especially when founders put their own money on the line. But for those who genuinely believe their idea is going to become huge, it’s worth the risk. And for these three entrepreneurs, it most certainly was worth it.
Sara Blakely
Today, the brand name Spanx is synonymous with shapewear, but when its founder, Sara Blakely, began the business, it was a high-stakes risk. Blakely funded the business in 2000 with $5,000 of her savings. She bootstrapped operations by handling as much as she could on her own, advertising and even modeling her product to retailers across the United States. The company quickly earned its first breakthrough: Spanx appeared on Oprah’s talk show. That appearance, in the company’s launch year, skyrocketed sales. By 2012, Blakely’s risk paid off even more when she became the world’s youngest self-made female billionaire. Impressive, given she started with just $5,000.
Brian Chesky & Joe Gebbia
Brian Chesky and Joe Gebbia are the founders behind Airbnb, which began as a unicorn startup. While today we know their risk paid off, when the two were getting started, it was far from a sure thing. Gebbia first got the idea when he realized that all of the hotels in his city of San Francisco sold out ahead of a major design conference. Years earlier, he took a risk and allowed a stranger to sleep on an air mattress in his apartment. Doing this had planted a seed that sprouted when he realized he and his roommate Chesky could take advantage of the overbooked hotel industry: they could rent their home to stranded designers. It was by no means glamorous for their first guests; three of them slept on air mattresses on the floor of an apartment (hence the name of the company), but it only cost them $20 a night, and they ended up loving it.
After this experience, Chesky and Gebbia were sure they were onto a billion-dollar idea—and Gebbia, who was unemployed and nearly through his savings, was willing to risk all he had left to get the idea up and running. However, the trust required for opening one’s home to a stranger and staying in a stranger’s home turned out to be a bigger barrier than anticipated, and the company faced many challenges. But they addressed these with ratings and strong customer service, and two years later, it started to pay off. The company is now publicly traded and is valued at $81.3 billion.
Crypto Mavericks: Early Believers
There are many stories of early crypto adopters—the ones who were willing to take a risk on an entirely new concept just to see what would happen. The most inspiring of these stories is that of Erik Finman, who became a millionaire by the age of 18 thanks to the Bitcoin investment he made at 12 years old.
While it may sound difficult to believe, this investment wasn’t just based on the whim of a 12-year-old who thought Bitcoin sounded cool. Finman was calculated in his decision. He was a brilliant kid, nurtured in a high-achieving academic family, with parents who held PhDs from Stanford and brothers who attended MIT. Unlike his family, Finman struggled with school. His parents were determined to see him get a college education, but Finman came to them with an offer: if he could become a millionaire before he was 18, he could skip college. His parents readily accepted the offer—after all, how often do you hear of self-made 18-year-old millionaires?
Finman had a plan; he received a $1,000 gift, and he put it all into Bitcoin in 2011. At the time, it was valued at $12 per coin. In the years to follow, Bitcoin fluctuated wildly, but Finman held off selling; he knew he was playing a long-term game, and it paid off immensely for the teen.
Instead of returning to school, he started a business. The business? An online education platform that offers struggling students an alternative path to education.
High-Risk, High-Reward: The Gambler Who Hit the Jackpot
Gambling is a classic example of risk-taking that most people engage in casually, whether at a physical casino or at online casinos that accept PayPal. However, for Don Johnson, a seasoned Blackjack player, gambling was more than a casual activity. He had developed a strategy to turn the odds in his favor. Johnson had been a high roller at casinos, though never a serious enough player to draw much attention from casinos. After playing for some time, he realized that even with the discounts offered by casinos to their high-paying clients, the odds were still stacked against him.
His solution? To negotiate with casinos to give him a higher discount on losses and minor alterations to the house rules, building off common offers made to high rollers to entice them to spend money at casinos. These helped reduce the house edge for the casino, giving Johnson better odds of winning.
In under a year, between December 2010 and April 2011, Johnson won $15 million in Atlantic City, $6 million from Tropicana, $5 million from Borgata, and $4 million from Caesar’s. He beat the house, costing the casinos millions, and walked away a millionaire.
The Thin Line Between Brave and Reckless
With the right vision, determination, and dedication, taking risks can have massive financial payoffs—whether it’s in business, investments, or gambling. To be as successful as these five individuals requires being calculated and appropriately cautious, not just blindly going out on a limb. If you do it right, you could end up being another story in the fast lane to fortune.
