Big rewards often come with big risks. While most investors play it safe, some take a gamble that others wouldn’t dare—and sometimes, that bet pays off in a massive way. These investments weren’t just risky; they were downright bold, often going against conventional wisdom.
From early tech startups to unconventional assets, here are 15 high-risk investments that made some people incredibly wealthy.
1. Bitcoin Before It Was Popular
When Bitcoin first launched in 2009, most people dismissed it as a joke. It had no real-world use, and early buyers were mostly tech enthusiasts. But those who held onto their coins saw life-changing returns.
A $1,000 investment in Bitcoin in 2011 would be worth over $30 million today. Despite extreme volatility, early adopters who believed in cryptocurrency’s potential saw some of the biggest financial gains in history.
2. Investing in Tesla When It Was Struggling
Tesla faced major doubts in its early years. Many investors thought it would go bankrupt, and short sellers bet against it constantly. But those who saw the potential in electric vehicles and stuck with Tesla through its ups and downs were rewarded handsomely.
Since going public in 2010, Tesla’s stock has skyrocketed, creating millionaires out of early believers. Today, it’s one of the most valuable car companies in the world.
3. Buying Apple Stock in the 1990s
Apple was on the verge of collapse in the mid-90s. The company was losing market share, and many assumed it wouldn’t survive. But investors who stuck with Apple—or bought in when Steve Jobs returned—made one of the best investments of all time.
The launch of the iPod, iPhone, and MacBook turned Apple into a tech powerhouse. A $1,000 investment in Apple stock in 1997 would be worth well over $1 million today.
4. The Facebook IPO
When Facebook went public in 2012, many believed it was overhyped. The stock initially dropped, and skeptics questioned its ability to make money. But those who held on saw enormous returns as Facebook (now Meta) grew into a social media empire.
What seemed like an uncertain bet at the time turned into one of the best-performing tech stocks of the last decade.
5. Investing in Amazon Before It Became a Retail Giant
In the late 90s, Amazon was just an online bookstore, and few people believed e-commerce would ever replace traditional retail. Many thought Jeff Bezos’ vision was too ambitious.
But investors who backed Amazon early have been rewarded beyond belief. A $1,000 investment at Amazon’s IPO in 1997 is worth millions today.
6. Netflix’s Shift to Streaming
Netflix started as a DVD rental company, competing with Blockbuster. When it shifted to streaming, many investors doubted the move, thinking internet speeds weren’t good enough for digital content.
Those who believed in the shift were handsomely rewarded. Netflix’s stock has grown over 40,000% since the early 2000s, turning skeptics into millionaires.
7. Buying Real Estate in a Market Crash
The 2008 financial crisis caused a massive housing market crash. While most people were too afraid to buy, savvy investors saw an opportunity.
Those who scooped up properties at rock-bottom prices made huge profits when the market recovered. Many of today’s wealthiest real estate investors built their fortunes by buying during a downturn.
8. Investing in SpaceX
Private space travel sounded like science fiction, and many doubted Elon Musk’s ability to compete with NASA. But early investors in SpaceX took a gamble on Musk’s vision.
Today, SpaceX is leading the commercial space industry, winning government contracts and making space travel more accessible. Those who got in early are now sitting on huge gains.
9. Collecting Rare Pokémon Cards
In the 90s, Pokémon cards were just a kids’ fad. Few thought they’d hold any value. But collectors who kept rare cards in mint condition saw massive returns.
A 1999 Charizard card, once worth a few dollars, now sells for hundreds of thousands. What seemed like a childhood hobby turned into a goldmine for collectors.
10. Investing in Ethereum Before It Took Off
Bitcoin’s younger sibling, Ethereum, launched in 2015 with little fanfare. Many dismissed it, thinking only Bitcoin mattered.
But Ethereum’s blockchain technology powered NFTs, smart contracts, and decentralized finance, making it one of the most valuable cryptocurrencies. Early investors saw returns in the thousands of percent.
11. Betting on Tesla’s Competitors
While Tesla led the electric vehicle revolution, smart investors also backed other EV makers like Rivian and Lucid.
These stocks have had their ups and downs, but as the world shifts toward electric vehicles, many of these early bets are paying off in a big way.
12. Investing in NFTs Early
NFTs (non-fungible tokens) seemed like a bizarre trend, but early investors who bought digital art, virtual land, and collectibles saw jaw-dropping profits.
While the market has cooled, those who got in early and sold at the right time made fortunes from digital assets.
13. Betting on Cannabis Stocks
As cannabis legalization spread, early investors jumped into cannabis stocks before they exploded. Companies like Tilray and Canopy Growth saw massive spikes when legalization expanded.
Not every cannabis stock succeeded, but those who timed it right made incredible gains.
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14. Investing in Tesla’s Battery Technology
While most investors focused on Tesla’s cars, others saw potential in its battery and energy storage technology.
Tesla’s solar and battery storage business is booming, and investors who bet on this side of the company saw massive returns.
Read More: 10 Signs You’re Better With Money Than You Think
15. Buying Art From Emerging Artists
Some collectors take risks on unknown artists, hoping their work will become valuable. Those who bought early pieces from now-famous artists have seen their investments grow by millions.
Art investing is unpredictable, but when it pays off, it pays off big.
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