Mark Cuban Reveals His Biggest Missed Investment That Cost Him Billions

Billionaire investor and owner of the Dallas Mavericks Mark Cuban, has a multifaceted life. The "Shark Tank" star has built a career creating and investing in many profitable companies.

During a recent interview on Kevin Hart's "Hart to Heart" talk show, however, Cuban shared about the one time he missed one of the biggest investments of his life. 

According to Cuban, Travis Kalanick, the co-founder of Uber Technologies Inc (NYSE: UBER), presented what was initially known as "Uber Cab" to him, and immediately drawing the interest of "Shark Tank" investor. 

However, when it came to negotiations, Cuban offered a lower valuation, proposing a $5 million valuation instead of Kalanick's $10 million valuation 

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Cuban said that his hesitation stemmed from reviewing Kalanick's budget, as the former believed the company needed more money for marketing and taxi cab commissions. His cautious approach influenced his decision during the negotiation process, he admitted.

Unfortunately, the deal did not come to fruition as Kalanick never returned to discuss further terms with Cuban. 

"250 grand on a $10 million valuation, it'd be billions," Cuban reflected on the podcast. 

During the interview, Hart shared a similar regret, recalling the opportunity he had to invest in Uber when talent manager Troy Carter had pitched the idea to him.  Hart said that Carter had described Uber as a platform where strangers would offer rides to others.

The comedian jokingly remarked, "Sounds like Murderville to me. This has got to be the stupidest thing I've ever heard." Looking back, Hard said he regrets not seizing the chance to invest in the company.

Founded in 2009 by Kalanick and Garrett Camp, Uber Technologies Inc. is a prominent rideshare company that went public in 2019. As of July 2023, its market cap stands at $94 billion.

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