Human Interest

Mark Cuban Passed On Early Investment in Uber That He Says Is Worth Billions Today: ‘Whoops’

'Hart to Heart' host Kevin Hart also confessed to missing out on an opportunity to invest in Uber during its early days

By Staff Author

Published on August 21, 2023 02:49PM EDT

Mark Cuban uber — Mark Cuban. Photo:
Richard Middlesworth/ABC via Getty; Smith Collection/Gado/Getty

Mark Cuban had a golden opportunity to invest in Uber before it took off, but he regrettably missed out.

During an appearance on the Peacock series Hart to Heart, the 65-year-old billionaire and host Kevin Hart revealed that they both missed early opportunities to invest in the ride-share company.

Cuban said he was approached by co-founder Travis Kalanick in 2009 after helping him save and sell another company called Red Swoosh.

At the time he approached Cuban with the offer, Kalanick said the company was valued at $10 million. Cuban said he would “do it at $5 million” valuation but ultimately “never” heard back.

“Whoops,” Cuban said. He later speculated, exactly, what his decision cost him. “Just think, if I would have given him $250,000 on a $5 million or $10 million valuation, it’d be billions.”

Initially, Cuban said he loved the idea behind Uber. But he also had concerns about the company when he was asked to invest, especially after looking at the budget.

“You’re going to have to spend a lot more on marketing and dealing with all the taxicab commissions that are going to try and put you out of business,” Cuban recalled telling Kalanick at the time. “So that’s the challenge that I see for you guys.”

Now, Uber is valued at about $90.5 billion, according to Yahoo Finance.

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Hart, 44, said he also missed a chance to invest in Uber. He claimed talent manager Troy Carter asked him to invest between $50,000 and $75,000 into the company, but that he ultimately didn’t bite.

When told what Uber was about, Hart said the concept “sounded like murder-ville” and suggested “this has got to be the stupidest s**t I’ve ever heard.”

Had he invested, Hart believes he would have made more than $100 million.

“There’s nothing worse than being pitched something you can’t see,” Hart said earlier in the episode.

After revealing his own missed opportunity with Uber, Cuban told Hart, "Don't feel bad."