But despite the chance, he posted on LinkedIn last week, he chose not to invest in Uber — a company that's now worth roughly $138 billion. It was "one of the greatest mistakes of my investing career," wrote Vaynerchuk, currently the CEO of Vaynerchuk Media. In 2009, Uber's co-founders sought funding at a $10 million valuation, serial entrepreneur Mark Cuban told Peacock's "Hart to Heart" last year. "I realized, Uber doesn't sell transportation ... Uber sells us time," Vaynerchuk wrote. "Just think: If I would've given him $250,000 on a [$10 million] valuation, it'd be billions," he said.

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Persons: Resy, Gary Vaynerchuk, Uber, Uber's, Mark Cuban, Peacock's, Hart, Vaynerchuk, Travis Kalanick, Garrett Camp, Vaynerchuck, Logan Paul, AJ Vaynerchuk, AJ, Cuban, Kalanick, Peacock Organizations: Twitter, LinkedIn, Uber, Vaynerchuk Media, CNBC Locations: New York City, NBCUniversal