Mark Cuban, Kevin Hart And An Investment Oversight They Both Regret

Mark Cuban is well known as one of the best businessmen and investors in the world. Kevin Hart is most often associated with his comedy acts and side-splitting exploits on the big screen.

But there's one thing the two have in common: They both missed out on — and regret — the opportunity to invest in Uber Technologies Inc. 

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Talking to each other on an episode of Hart's talk show, "Hart to Heart,"  the two power players realized that they both missed out on a big opportunity. 

On one hand, Hart dismissed the idea of Uber because the business model sounded  "like Murderville" to him. He was asked to invest somewhere between $50,000 and $75,000, which he estimates would be worth roughly $100 million today.

If that sounds bad, Cuban has it even worse. The owner of the NBA's Dallas Mavericks had an early conversation with Uber Co-Founder Travis Kalanick about investing. At the time, he believed that the $10 million valuation was too high, so he offered to invest at a $5 million valuation. The two never reconnected, and a deal was never made.

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Cuban noted that an investment of $250,000 at either valuation would be worth billions today. That's a hard pill to swallow, even when you're already a billionaire.

While this is a big miss for both Cuban and Hart, they have done well for themselves in other investments. For example, in 2019 Cuban said he owned approximately $1 billion in Amazon.com Inc. stock. 

As for Hart, he's picked many winners through Hartbeat Ventures, the venture capital firm in which he is a general partner. 

This is a good lesson for anyone who's missed out on an investment opportunity. You won't get them all right, but giving up guarantees that you never have success in the future.

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