The biggest mistakes 7 billionaires have made with their money

You might think that the richest people in the world have figured out exactly what works in business and their own financial life. But you'd be very wrong.

Billionaires make money mistakes all the time, and even admit to doing so. Some even claim their errors actually help them learn the right ways to get ahead.

From Jeff Bezos losing out on billions for Amazon to Oprah's botched TV rollout, here are 7 famous billionaires' worst money moves that you might not even realize they made.

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Bill Gates' Apple assist

In 1997, when Apple was at a low point and failure looked not only possible but likely, Bill Gates' Microsoft made a $150 million investment in its rival and committed to providing software for its computers. While Gates' move was strategic at the time, helping to ease the government's worries that Microsoft was anticompetitive, many have seen it as the tech icon's ultimate blunder in retrospect. Steve Jobs not only brought Apple back from the brink but ended up dominating Microsoft in a number of realms, especially mobile phones, making Apple the most valued company in the world in 2017. One wonders what would have happened to Apple—and how valuable Microsoft and therefore Gates would be—if not for Gates' lending hand back in the day.

Jeff Bezos' leak of 'billions'

It's been a banner year for Amazon head Jeff Bezos, who became the richest person in the world, surpassing Bill Gates, and even hit a net worth of $100 billion. But he admitted in 2014 that his penchant for experimentation has led to Amazon losing a lot. "I've made billions of dollars of failures at Amazon.com. Literally," Bezos told the Business Insider Ignition conference in New York City. He said that having to review them would be like "a root canal with no anesthesia." While gambles like Amazon's Kindle and Echo have paid off, one regret is surely the Fire Phone that didn't sell and forced the company to write off $170 million on losses.

Oprah's ambitious blunder

After decades as the queen of daytime TV, Oprah Winfrey could have quietly ridden off into the sunset when The Oprah Winfrey Show finished. But instead she set her sights even higher, launching her own network in 2011. But OWN struggled mightily in its early days, with a string of flops, and Oprah admitted of the project, "Had I known that it was this difficult, I might have done something else." She said she unveiled the network before it was ready, and that a book about the rollout could be called "101 Mistakes." The gambit led to losses around $330 million and in that period she nearly suffered a nervous breakdown. But in typical Oprah fashion, she rebounded and the network is now enjoying a string of scripted hits.