Mark Cuban Passed On The Chance To Own Part Of Uber's $97 Billion Empire Because It Was Too Risky — Now He Says It's His 'Biggest Miss Ever'

Billionaire entrepreneur and “Shark Tank” panelist Mark Cuban has a knack for identifying lucrative investment opportunities. But despite his expertise and successful portfolio, there have been instances where he passed on opportunities that later turned into massively successful companies.

In a conversation with actor Kevin Hart on the talk show “Hart to Heart,” Cuban delved into a significant decision he made nearly a decade before Uber Technologies Inc.’s record-breaking 2019 public debut. Cuban had been approached by Travis Kalanick, Uber’s co-founder, with an investment opportunity that could have resulted in a multibillion-dollar payoff for the business mogul.

Don’t Miss:

• Peter Thiel, Mark Cuban and Warren Buffett funded early-stage startups and made millions. You don’t need to be a well-connected billionaire to do the same

• Operating a fully booked hotel is beyond stressful, but it’s about to become much more efficient thanks to one startup. It amassed $5.5 million in its seed round, quintupled its customer base in nine months and is looking for investors.. 

Kalanick offered Cuban the chance to invest $250,000 at a valuation of $10 million. Fast forward to today, and the ride-hailing service has a market capitalization of $97 billion. Had Cuban accepted the original offer, his stake could have been valued at around $2.3 billion, disregarding any share dilution that might have occurred.

However, Cuban decided against the investment. He was cautious about the regulatory challenges and legal conflicts with taxi commissions the fledgling company would encounter. Instead, Cuban offered to invest at a valuation of $5 million, a proposal to which Kalanick never responded.

While Cuban has often displayed a keen business sense, he said this particular decision was his “biggest miss ever.” He mentioned that another investor took the opportunity he had passed on.

Trending: Blackstone made a $13 billion bet on the growth in student housing. Here’s how you can carve out your own piece of the student housing market with just $500.

Despite missing out on Uber, the entrepreneur has certainly had his share of major successes in the venture capital space. When he appeared on “The Ellen DeGeneres Show,” Cuban cited a $250,000 investment in Cycloramic as one of his most successful deals. The company, founded by Bruno Francois, initially focused on a selfie-taking app but pivoted to specialize in photographing cars. The move led to a $22 million acquisition. It wasn’t necessarily the amount of the acquisition that led him to deem this move so impressive. The company went from zero to $22 million, which he said was “The American Dream.”

In 2000, Cuban purchased the NBA team Dallas Mavericks for $285 million from Ross Perot Jr. At the time of the acquisition, the Mavericks were far from a championship-caliber team, but Cuban’s hands-on approach and willingness to invest in players, facilities and fan experiences revitalized the franchise. Under his ownership, the Mavericks have experienced significant success, including winning their first NBA championship in 2011. Today, the Mavericks franchise value is $3.3 billion.

Read Next: 

• Passive income investments are one of the most trusted methods for riding out a recession, so it’s no surprise that people are turning to high-yield notes that pay a fixed 7.5% to 9%.

• Are Wall Street's days numbered? This platform's game-changing solution could disrupt finance forever.