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Mark Cuban Shares the Story of How He Passed on the Opportunity to Invest in Uber

Even the most accomplished investors will make a wrong decision from time to time. For businessman and Shark Tank star Mark Cuban, that bad decision was passing on the opportunity to invest in Uber.

During a recent appearance on comedian Kevin Hart’s show Hart to Heart, Cuban shared how Uber cofounder Travis Kalanick approached him in 2009 with an offer to get a piece of the transportation app. The two knew each other since Cuban previously invested in Kalanick’s peer-to-peer file-sharing company Red Swoosh and saved it from bankruptcy.

 According to Cuban, he was interested in backing up Kalanick once again but didn’t think his valuation of $10 million was appropriate. Cuban offered an investment at a $5 million valuation but never heard back from Kalanick again.

“He got somebody else,” Cuban shared. “Whoops.”

Hart also had the opportunity to invest in Uber but also decided to pass on it. He was asked to put in $50,000 to $75,000 in the company’s early days, missing out on hundreds of millions of dollars.

On the other hand, Cuban shared that Kalanick asked for $250,000 from him. Considering that Uber is now worth around $90 billion, Cuban missed out on more than $2 billion.

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