Sometimes, playing it safe won’t get you ahead. Some of the wealthiest people in history made their fortunes by going against conventional wisdom—taking big risks, making unpopular decisions, and betting on ideas that others dismissed.
But not every bold move pays off. These strategies walk a fine line between genius and disaster. Let’s take a look at ten controversial money moves that turned out to be wildly profitable.
1. Dropping Out of College to Build a Business
College is often seen as the key to success, but some of the richest people in the world—like Bill Gates, Steve Jobs, and Mark Zuckerberg—dropped out to chase their ideas. They risked it all on their startups, choosing real-world experience over a degree.
For most people, skipping college is risky. But for these entrepreneurs, it allowed them to focus fully on innovation, and their bets paid off in billions. That said, this move only works if you have a clear plan, relentless drive, and an idea strong enough to disrupt an industry.
2. Investing Everything in a Single Stock
Most financial experts warn against putting all your money into one investment. But some investors ignored this advice—and made fortunes. Take Elon Musk, who poured nearly all his PayPal earnings into Tesla and SpaceX. Or early Amazon employees who kept all their stock instead of selling when it first took off.
This move can be a massive win if you pick the right company at the right time. But for every success story, there are thousands of people who lost everything betting on the wrong stock.
3. Buying Bitcoin Before It Was Popular
When Bitcoin first emerged, many experts dismissed it as worthless internet money. But a few early believers took the risk and bought in when prices were under $1. Those who held onto their Bitcoin through the wild swings became millionaires—or even billionaires.
Of course, for every Bitcoin success story, there are investors who lost everything on failed cryptocurrencies. Timing and patience were key for those who made it big.
4. Starting a Business During a Recession
Most people wait for the economy to improve before launching a business. But some of the biggest companies—like Uber, Airbnb, and Netflix—were founded during economic downturns.
When times are tough, competition is lower, and new solutions are in demand. Those who took the leap and built businesses during recessions often found huge success once the economy bounced back.
5. Borrowing Heavily to Invest in Real Estate
Taking on massive debt to buy property is risky, but for some, it’s the key to wealth. Real estate moguls like Grant Cardone built fortunes by using leverage—borrowing money to buy properties, then using rental income to pay off loans and grow their portfolios.
This move only works if property values and rental demand stay strong. If the market crashes or interest rates rise, over-leveraged investors can lose everything.
6. Quitting a Stable Job to Chase a Passion
Most people hold onto secure jobs, but some of the wealthiest individuals walked away from steady paychecks to chase bigger dreams. Jeff Bezos left a lucrative Wall Street career to start Amazon, and Oprah left a stable TV anchor job to create her own media empire.
Quitting a job without a plan is reckless. But when done strategically—with a vision, a financial cushion, and a clear path—this controversial move has led many to massive success.
7. Living Dirt Cheap to Save and Invest Aggressively
While many people spend more as they earn more, some extreme savers take the opposite approach. Millionaires like Warren Buffett and frugal early retirees follow ultra-low-cost lifestyles, investing nearly all their income.
This method, often called the FIRE (Financial Independence, Retire Early) movement, isn’t for everyone. It requires serious discipline and sacrifices. But those who stick with it can retire decades earlier than most.
8. Buying Failing Businesses and Turning Them Around
Most investors avoid struggling businesses, but turnaround specialists see opportunity. Billionaires like Carl Icahn and Warren Buffett have made fortunes by buying undervalued, failing companies, fixing their problems, and selling for huge profits.
This strategy requires deep business knowledge and a strong stomach. Buying a failing business is risky—if you can’t turn it around, you lose everything. But for those who can, the rewards are enormous.
Read More: The 10 Most Underrated Ways to Save Money That No One Talks About
9. Creating Controversial or “Hated” Products
Some of the most profitable businesses started with products people initially mocked or dismissed. The iPhone was ridiculed before it became a global must-have. Tesla was written off as an impossible dream. Even bottled water was once considered a ridiculous idea.
The lesson? If you truly believe in a product, market, or idea, public skepticism doesn’t mean failure. Many of today’s biggest innovations started as controversial bets.
Read More: The 10 Most Overhyped Investment Strategies (and What Works Instead)
10. Selling Everything and Moving to a New Market
Some entrepreneurs and investors became wealthy by leaving everything behind and starting fresh in a booming market. Silicon Valley, Dubai, and Shenzhen have all seen massive success stories from people who relocated to chase opportunities.
This move is high risk—relocating costs money, and there’s no guarantee of success. But for those who pick the right time and place, the payoff can be life-changing.
Read More: 10 Money Moves You’ll Probably Regret in 10 Years
