In a recent interview on the Peacock YouTube channel, Kevin Hart and Mark Cuban opened up about a big mistake they both made. Despite their huge success, they missed out on a chance to invest in Uber when it was just getting started. This decision, they admit, still haunts them today.
Uber’s Humble Beginnings
Uber wasn’t always the giant company it is now. Back in 2009, when Travis Kalanick and Garrett Camp founded it, the idea of ride-sharing was brand new. People weren’t sure if it would work. Uber faced a lot of challenges, including legal battles and the fact that many people didn’t like the idea of getting into a car with a stranger.
Kevin Hart’s Missed Chance
Kevin Hart’s friend, Troy Carter, tried to get him on board with Uber early on. Carter pitched the idea to him, saying, “Kev, you gotta invest in this thing called Uber.”
But Hart didn’t buy it. “Strangers giving rides to other strangers? That sounds like ‘Murderville’ to me!” he joked.
Despite Troy’s insistence that Uber was the next big thing, Kevin passed. Now, with Uber worth billions, he can’t help but think about what might have been. “If I had just taken the leap,” he says, “who knows where I’d be now?”
Mark Cuban’s What-If Moment
Mark Cuban, the billionaire investor, also had a shot at Uber. Travis Kalanick himself pitched the idea to Cuban after selling his previous company.
Cuban liked the idea but hesitated when Kalanick valued Uber at $10 million. “I loved the idea,” Cuban said, “but I told him I’d do it at a $5 million valuation.”
Kalanick never came back, and Cuban didn’t follow up. Now, Cuban admits that passing on Uber was a big mistake. “It could have been billions,” he reflects, thinking about how much he missed out on.
The Impact of a Lost Opportunity
For both Hart and Cuban, this wasn’t just about losing money. It’s a reminder that even the most successful people can make mistakes. A small investment in Uber back then could have turned into hundreds of millions, if not billions, today.
But it’s not just the money. Missing out on Uber stings because it’s become such a massive success. Hart learned that sometimes, you need to take a risk, even if an idea sounds crazy. Cuban learned that you shouldn’t let small details, like valuations, stop you from seeing the bigger picture.
Lessons for the Future
Both Hart and Cuban have taken lessons from this experience. In the world of investments, the craziest ideas can sometimes be the most successful. Hart now believes in staying open-minded and not letting fear get in the way. Cuban thinks it’s important to not get stuck on the small stuff and to always look at the big picture.
A Lesson for Us All
The story of how Kevin Hart and Mark Cuban missed out on Uber is a powerful reminder that even the best of us have regrets. Business is unpredictable, and no one has a perfect record.
But it’s also a story of growth. Both Hart and Cuban have used this experience to make better decisions in the future. While they might never forget the missed opportunity with Uber, they’ve continued to succeed. Their story reminds us all to trust our instincts, take risks, and stay open to new ideas—because you never know when the next big thing will come along.
