In 2009, billionaire Mark Cuban didn’t invest in Uber for good reason. But nearly 15 years later, he still deeply regrets not doing so.

In 2009, Uber co-founder Travis Kalanick (Travis Kalanick) approached Cuban, hoping to invest in Uber at a valuation of $10 million. The ride-sharing giant’s market cap is currently about $90 billion.

Cuban describe Missed the chance for the latest episode heart-to-heart, Kevin Hart’s talk show about peacocks. “I said, ‘I’m going to do this at a $5 million valuation,'” Shark Tank Star recalled.

He foresees regulatory pain for Uber and warns Kalanick that the taxi commission will “try to put you out of business.” Of course, Uber has overcome these hurdles and various controversies on the way to its current valuation.

If Cuban had invested $250,000 in Uber in 2009, the investment worth it now $2.3 billion.

“I’m doing okay, but still,” said Cuban, who later co-founded Cost Plus Drugs (which is now disrupting the likes of CVS and Cigna Group) and owns the Dallas Mavericks.

Kalanick didn’t get back to Cuban to talk about Uber’s proposal. “He’s got someone else,” Cuban said, adding, “Yeah.”

Cuban’s net worth is now estimated at over $5 billion, so he’s barely affected. But even billionaires will feel the pain of missed opportunity for years to come.

In 2017, he meditation Uber mistakes he made at SXSW, saying: “When you try to disrupt something like Travis did, sometimes you have to get ready, fire, aim, and break in and think you’re going to deal with regulation later. question.” “.

He added, “If you really believe and you do have something that you think is going to turn the world upside down, please bring it to me. I won’t make the same mistake a second time.”

Cuban pointed out that he himself is a company called radio networkOnce was a young entrepreneur who forged ahead despite regulatory hurdles.acquisition by yahoo radio network In 1999 it was $5.7 billion.

Of course, Cuban wasn’t the only one passing up a golden opportunity. In 2000, Blockbuster had the opportunity to buy Netflix for $50 million. Today, Netflix has a market cap of about $180 billion, while Blockbuster has largely disappeared from memory.

Blockbuster’s then-CEO John Antioco dismissed Netflix as a niche business and said “the mania of the dot-com bubble was completely exaggerated.” according to Netflix co-founder Marc Randolph recounted the streaming giant’s origins in a 2019 book.In April, Randolph tweet Blockbuster exec “laughed us out of the room”.

Cuban didn’t laugh Kalanick out of the room — he even said he “liked” his idea. However, that valuation put him off, and Kalanick “never came back to me.”


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