Mark Cuban Reflects On Investment That Slipped Through His Fingers: 'Yeah, It Wasn't A Mistake, It Was Just…It Was A Mistake'

Mark Cuban, the vibrant personality we all know from Shark Tank, had a chuckle about a major “oops” moment – passing up the chance to invest early in Uber.

What Happened: Chatting on the Lex Fridman Podcast, Cuban opened up with his usual mix of humor and insight, revealing how he passed on the chance to invest in Uber, a decision that would’ve turned his $250,000 in 2009 into a cool $4 billion (approx) today.

The missed opportunity would have seen his investment soar alongside Uber’s valuation which currently stands at a staggering $160 billion.

Fridman asked “Beautifully said. You have made some mistakes in your life?”

“Yeah, a lot of them,” Cuban replied.

“One of the bigger ones on the financial side we could say is Uber,” again asked Fridman.

“Yeah, we call that not doing something. Yeah, it wasn't a mistake, it was just… It was a mistake,” Cuban as both laughed.

Cuban’s Hesitation: Evaluating The Challenges And Costs Of Uber’s Ride-Sharing Concept

Uber co-founder Travis Kalanick pitched the ride-sharing concept to Cuban in 2009 at a $10 million valuation. Despite their history with Kalanick’s previous venture, Red Swoosh, which Cuban had invested in and saw a fruitful exit, the billionaire hesitated.

Cuban’s main concern? Uber’s potentially uphill battle against the taxi commissions and the heaps of cash that would be needed for marketing.

“Your biggest challenge is going to be you're going to have to fight all the incumbent taxi commissions. They're going to want to put you out of business. That's going to be a challenge, and I think you don't have enough money designated for marketing to get all that done,” Cuban recounted telling Kalanick.

See also: Mark Cuban Dispels Rumors About AI Bubble, Comparing It To Dot-Com Era ‘Frothiness’: ‘There Were…Companies With Just A Website And Going Public’

Reflecting on the decision, Cuban’s not losing sleep over it. Instead, he shares his story with the wisdom of someone who knows the tech game’s highs and lows.

Cuban goes on to mention how much admires Kalanick’s relentless ambition. “I told him, Travis, the best thing about you is you’ll run through walls and break down barriers. The bad thing about you is you’ll run through walls even if you don’t have to,” Cuban shared.

Fridman and Cuban dove into the lighter secrets of becoming a billionaire over the course of the podcast, with Cuban remarking that timing, proximity, and perhaps a pinch of luck play pivotal roles. Echoing his playful banter, Cuban also mentioned how Facebook’s Mark Zuckerberg initially created Facemash, hinting that sometimes, big ideas start from humble (or humorous) beginnings.

Watch Full Episode Here:

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