Mark Cuban is one of the richest men in the world, but even the savviest businessmen have their big misses.
The “Shark Tank” star guested on Kevin Hart’s “Hart to Heart” talk show streaming on Peacock, and the two recounted missing on one of the biggest investments of their lives: Uber (UBER) -).
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Cuban said Travis Kalanick, co-founder of Uber, pitched the idea of what was then “Uber Cab” to him, and he “loved it.” But Cuban ended up lowballing Kalanick, leading to one of the biggest investment misses of his life.
“He had a valuation of $10 million, I said I’d do it at $5 million … [he] never came back to me,” Cuban said.
Cuban explained that his trepidation came from seeing Kalanick’s budget because he believed the company needed to spend more on marketing and taxi cab commissions.
“250 grand on a $10 million valuation, it’d be billions,” Cuban said.
Hart felt similar grief as Cuban as he was also offered to invest in Uber after being pitched by talent manager Troy Carter. Hart said that Carter told him that Uber would be strangers giving other people rides.
“Sounds like Murderville to me,” the comedian joked. “This has got to be the stupidest shit I’ve ever heard.”
Hart said that to this day, he thinks about the $50,000 investment that could have brought him hundreds of millions in return.
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Uber Technologies Inc. was founded in 2009 by Kalanick and Garrett Camp. The rideshare company went public in 2019 and has a market cap of $94 billion as of July 2023.
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