4 Billionaires Like Mark Cuban Who Did Crazy Things To Get on Top
If you're scraping by until your next paycheck, imagining a billion dollars probably feels impossible. Sure, luck and timing play a role for the world's richest people, but many of today's biggest names got there by doing things that looked completely insane at the time.
Real-life Richie Riches like Warren Buffett, Elon Musk and Mark Cuban built empires by making bold, unconventional bets when the odds were stacked against them. Overnight success stories still dominate headlines, but the truth behind extreme wealth is far messier: risked savings, torched reputations, and years of uncertainty before any payoff arrived.
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Here are four billionaires who did shocking, high-risk things to get on top — proof that the road to extraordinary success sometimes starts with a decision everyone else calls crazy.
Mark Cuban
Estimated net worth: $6 billion
This successful entrepreneur-turned-billionaire sold his first company, MicroSolutions, at the tender age of 31. Now he's known for more high-risk investments, such as streaming radio over the internet in 1995 (Broadcast.com) and launching a disruptive pharmacy, Cost Plus Drugs, to upend industry pricing.
During the lean years of couch surfing, learning and building, he drove a raggedy car, wore run-down clothing and lived as frugally as possible. Cuban, a young entrepreneur, basically gave up the luxuries of life in his 20s to set the stage for a lifetime of successful investing and business dealings down the road.
Warren Buffett
Estimated net worth: $145 billion
Buffett, currently the world's tenth richest man, knows his way around an investment or two. His approach to acquiring companies and securities goes against the grain. He regularly invests in stocks when most investors are running away from them.
In fact, Buffett is known for making more than a few risky acquisitions (or buying substantial positions) of companies in dire straits. For example, Buffett's Berkshire Hathaway gave Goldman Sachs a $5 billion infusion during the 2008 economic crisis. The big gamble was believing Congress would act and buy troubled assets from banks like Goldman Sachs. Buffett commented on the deal, "If I didn't think the government was going to act, I would not be doing anything..."
Estimates of Buffett's profits from the transaction exceed $3 billion, with potential for more down the road.
Buffet's advice? "Be fearful when others are greedy and greedy when others are fearful." What's crazier than ignoring your internal fear factor and going for the gusto anyway?
Richard Branson
Estimated net worth: $3 billion
If you wanted to make an impression on the 1970s punk rock scene in England, the first thing you had to do was troll the Queen of England's silver jubilee with a controversial song about Her Highness and the British Empire to boot.
This publicity stunt by the Sex Pistols, a band signed to Richard Branson's Virgin Records label in 1977, went down in anti-establishment history. Though he is now known for other controversies, it was a risky move wholly supported by Branson, and it paid off for him handsomely. The band's popularity exploded and paved the way for Branson's record label to sign some of the world's most famous musicians, including the Rolling Stones, Culture Club, Mariah Carey and Tina Turner.
Elon Musk
Estimated net worth: $927 billion
Musk, the richest man in the world, founder and CEO of Tesla and the former controversial head of DOGE, had a start-up teetering on the brink of disaster in 2008. At one point, he wasn't even sure he'd make payroll, but knew his fledgling company had to stay afloat. To make sure his employees got paid, he made the ultimate sacrifice. The last $3 million he had to his name was used to pay his employees to keep Tesla running.
After being tapped out on cash, Musk said he had to borrow money from friends for his own rent. Tesla went public in 2010 and earned him more than $600 million.
Aja McClanahan contributed to the reporting for this article.
This article was provided by MoneyLion.com for informational purposes only and should not be construed as financial, legal or tax advice.