Uber co-founder reveals his biggest financial regret: I missed out on investing in Uber twice

Gary Vaynerchuk, Resy co-founder and a well-known entrepreneur, invested in several companies that are now widely recognized, including Facebook, Twitter, Tumblr, Snap, and Venmo, as stated on his website.

Although he had the opportunity to invest in Uber last week on LinkedIn, he decided not to do so, resulting in what he considers one of the biggest mistakes of his investing career. Vaynerchuk, CEO of Vaynerchuk Media, was present when Uber was founded and still passed on the investment opportunity twice.

In 2009, Uber's co-founders sought funding at a $10 million valuation. If Vaynerchuk had invested $25,000, as he did with other investments at the time, his money would be worth roughly $345.1 million today, based on Uber's current market capitalization.

In 2019, Vaynerchuk revealed that he was friends with Uber co-founders Travis Kalanick and Garrett Camp, but decided not to participate in the company's angel investment round due to his lack of confidence in Uber's direction, as reported by CNBC Make It.

In 2022, on the "Impaulsive with Logan Paul" podcast, Vaynerchuck expressed skepticism about Uber's success because he had seen two of his own side hustles fail, and Kalanick and Camp were also maintaining full-time jobs elsewhere while working on their startup.

In 2013, two years after AJ Vaynerchuk took the first Uber ride in New York City, Vaynerchuk posted on LinkedIn about his experience with the app and had an epiphany.

"Uber doesn't sell transportation, but rather offers us convenience by allowing us to easily hail cabs with our phones, reducing the friction in our travel experience," Vaynerchuk wrote.

"People value time over everything," he added.

Cuban also passed up an opportunity to invest in Uber at its $10 million valuation, despite previously investing $1.7 million in Kalanick's Red Swoosh networking company.

Cuban expressed interest in investing in an app that could replace taxi cabs, but he wanted a $5 billion valuation, he stated. However, Kalanick did not respond to the counteroffer, Cuban noted.

He stated, "If I had given him $250,000 on a $10 million valuation, it would have resulted in billions."

CNBC has the exclusive off-network cable rights to "Shark Tank," which includes Mark Cuban as a panelist. Peacock is the streaming service of NBCUniversal, the parent company of CNBC.

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