Mark Cuban passed on Uber when it was worth $10 million or less. He missed out on billions of dollars in profits.
- Mark Cuban says he turned down the chance to invest in Uber at a $10 million valuation.
- Uber's market value has surged by over 9,000-fold since then to north of $90 billion.
Mark Cuban turned down the chance to invest in Uber at a valuation of no more than $10 million — just over 0.01% of the ride-hailing company's $91 billion market capitalization today.
The "Shark Tank" star bemoaned the missed opportunity during a recent episode of "Hart to Heart," actor Kevin Hart's talk show. Cuban recalled that Uber cofounder Travis Kalanick invited him to invest $250,000 at a $10 million valuation, almost a decade before the company went public in 2019.
Cuban pushed back, correctly predicting that Uber would face regulatory hurdles and costly battles with taxi commissions as it worked to disrupt the transportation industry. He offered to invest at a $5 million valuation, but Kalanick didn't respond.
"He got somebody else," Cuban said. "Whoops."
Cuban's $250,000 would have secured him a 2.5% stake in Uber at a $10 million valuation. Ignoring any dilution, his shares would have been worth $2.3 billion as of Friday's close — a roughly 9,200-fold gain on his investment.
The technology billionaire and Dallas Mavericks owner might have been able to invest in Uber on even more attractive terms. In 2019, he tweeted out an email exchange with Kalanick from 2010, in which Cuban wrote that he "wouldn't touch a 2mm valuation, let alone 5mm."
If Cuban did have a chance to invest $250,000 at a $5 million valuation, and he took it, his 5% stake would be worth $4.6 billion today, all else being equal. Unsurprisingly, Cuban labeled his decision to pass on Uber his "biggest miss ever."
Cuban seems to have learned his lesson. At the SXSW conference in 2017, he encouraged anyone with an idea to disrupt the world to get in touch with him. "I won't make the same mistake twice," he said.
Uber stock has soared 81% this year, but at $45 it still trades around its IPO price, more than four years after joining the public market.
Cuban is far from the only investor to let a golden opportunity slide him by. Elon Musk has repeatedly noted that Warren Buffett and Charlie Munger declined to invest in Tesla at a $200 million valuation in 2008, meaning they potentially missed out on making more than 3,000 times their money.