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Mark Cuban seems to be doing pretty well for himself when you consider the man who owns the Dallas Mavericks has an estimated net worth north of $5 billion—although that number could be significantly higher if he hadn’t passed on the chance to invest in Uber.
Cuban was basically set for life after Broadcast.com (the company he acquired in the mid-1990s) sold to Yahoo in a $5.7 billion stock deal that was finalized around a year before the dot-com bubble burst in spectacular fashion.
While he could’ve easily rested on his laurels, Cuban turned his attention to the world of investing, and the products that have earned his seal of approval on Shark Tank represent a fairly small chunk of the many different companies he’s had in his portfolio at some point in time.
You don’t need to have an MBA to know even the most seasoned businessperson can have trouble identifying the startups that have the potential to become the next unicorn, and you’d be hard-pressed to find any veteran investors who don’t have a story or two about passing on a company that eventually became The Next Big Thing.
According to CNBC, Cuban is certainly no exception, as it’s safe to assume he regrets his decision to turn down the chance to invest in a little ride-sharing venture known as “Uber” when it was still in its relative infancy.
Cuban shared that tidbit with Kevin Hart (who also turned down the chance to invest in Uber) during an episode of Hart to Heart where the former revealed co-founder Travis Kalanick gave him the opportunity to invest $250,000 for a 2.5% stake that would’ve valued Uber at $10 million.
While Cuban admitted he loved the idea, he unsuccessfully lobbied to get Kalanick to offer him 5% for the same price (which would’ve valued Uber at $5 million) and subsequently missed out on the chance to get in on the ground floor.
If we assume Cuban had indeed invested in Uber at that point and held on to all of those shares to this day, he could have turned that $250K into around $2.25 billion based on the company’s current market cap.
That’s gotta sting a little bit.