Investing is not a risk-free path to millions—let alone billions. Yet there are stories of people who bet on what seemed like a crazy idea, a company on the brink of collapse, or a garage project… and won. From a chef at Google to Jeff Bezos’s parents to George Soros’s bet against the British pound—here are eight investments that initially looked like pure gambling, but ultimately changed financial history.
The Google Chef Who Borrowed Money to Buy Shares
In 1999, Charlie Ayers Jr. worked as a personal chef in Silicon Valley. When he heard about a small company called Google, he had no idea what a search engine even was. Still, he applied for a head chef position—and when he didn’t receive a response, he began sending his homemade pies to Google. It worked. He became the chef for Google’s first 50 employees. A few years later, a financial advisor recommended that he buy shares before the company went public. Ayers borrowed $14,000 from his father, with a warning that if it turned out to be a scam, he would have to repay every dollar. When he left Google in 2006, his 700,000 shares were worth approximately $40 million (around $62 million today). He opened his own restaurant and repaid his father in full.
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George Soros and “The Day the Pound Fell”
George Soros survived the Nazi occupation of Hungary, studied at the London School of Economics, and went on to build successful investment funds. He made history in 1992 when he bet $10 billion against the British pound. At the time, the currency was overvalued, and Soros believed a collapse was inevitable. He traded so aggressively that he forced the Bank of England to capitulate. On what became known as Black Wednesday, he earned roughly $1 billion, which would be more than $2 billion today. The move cost Britain billions of pounds and led to its exit from the European Exchange Rate Mechanism.
Netflix: When Everyone Was Leaving, Icahn Was Buying
In 2011, Netflix decided to switch exclusively to streaming. The result was immediate backlash: 800,000 users canceled their subscriptions. Many investors panicked, but Carl Icahn did not. In 2012, he invested $321 million in Netflix and acquired a 10% stake. According to Business Insider, the investment earned him approximately $1.9 billion. He exited the company in 2015 and, according to estimates, missed out on a potential additional $6.4 billion. Even so, it remained one of the most profitable moves of his career.
Warren Buffett and a Billion-Dollar Candy Business
In 1972, Warren Buffett bought See’s Candies for $25 million. At the time, the brand was barely viable and generated annual profits of $4.2 million. Half a century later, Buffett admitted that See’s Candies had brought him more than $2 billion in pre-tax profits—a return of roughly 8,000 percent. The sweets also became a tradition at Berkshire Hathaway meetings. In 2013 alone, the company purchased six tons of candy.
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An Energy Drink from a Thai Pharmacy
In 1984, Austrian entrepreneur Dietrich Mateschitz was suffering from jet lag while in Thailand. Locals offered him a sweet drink called Krating Daeng. It helped. Mateschitz saw global potential in the product. Together with its creator, Chaleo Yoovidhya, he invested one million dollars (around three million today) into a brand that would later be called Red Bull. Today, the company sells more than 12 billion cans a year, and the brand is valued at an estimated $17 billion.
Nike Rescues Converse
In 2001, the Converse brand filed for bankruptcy. Two years later, Nike acquired it for $305 million (around $542 million today). Under Nike’s leadership, sales of the iconic Chuck Taylor shoes began to rise again. A company once on the brink of collapse returned to its position as a global player.
Parents Who Bet on Their Son’s Garage
Jeff Bezos founded Amazon as an online bookstore in his garage. In 1995, he convinced his parents to invest $245,573. He openly told them it was a “big gamble” and that the project would most likely fail. Amazon surpassed a market capitalization of one trillion dollars in 2018. If Bezos’s parents had held onto their shares, they would have been worth approximately $30.7 billion in 2020, according to Bloomberg.
Apple’s Third Man
Mike Markkula was lured out of early retirement by Steve Jobs and Steve Wozniak. In 1977, he invested $250,000 in Apple in exchange for a 30% stake and became the company’s financial backbone. Apple went on to become the first company valued at one trillion dollars and today is approaching a valuation of $3.4 trillion. Markkula left Apple in 1996, and it is unclear how many shares he retained. His net worth today is estimated at $1.2 billion.
What Can We Learn from These Stories?
Each of these investments looked like a reckless risk at the time. They all share three things: belief in the future, the courage to go against the crowd, and the ability to see potential where others saw only problems. This does not mean that everyone should gamble their savings on a garage startup. But it does show that the greatest returns often do not come from certainty, but from the moment when vision meets courage.
