In an episode of Hart to Heart, Kevin Hart’s talk show, both Hart and billionaire investor Mark Cuban shared a regretful tale that might make any entrepreneur cringe: they both passed on the chance to invest in Uber during its early stages.

Uber, which has since become a global powerhouse, wasn’t always an obvious success story. When pitched to these two stars, it sounded more like a recipe for disaster. Kevin Hart, in his usual comedic style, recalled dismissing the idea as “Murderville,” unable to wrap his head around the concept of strangers getting into cars with other strangers. On the other hand, Cuban was ready to invest but only at a lower valuation. He let the opportunity slip through his fingers when his offer wasn’t accepted.

Troy Carter, music manager turned tech mogul, told Hart, “There’s this thing, man. It’s called Uber. You got to invest in it.” But, “There’s nothing worse than being pitched something that you just can’t see,” Hart told Cuban.

“There’s an app, and you say you need a ride, and whoever’s close to you, that is like one of the drivers under our app will come get you,” continued Carter. But Hart simply told him, “Sounds like Murderville to me. This has to be the stupidest shit I ever heard.”

Fast-forward to 2024, and Uber’s success speaks for itself. The company reported revenue of over $37 billion in 2023, with a market cap exceeding $150 billion and a 19% year-over-year increase in gross bookings in the second quarter of 2024 alone. But Uber hasn’t stopped at ride-hailing. The company dominates the food delivery market through Uber Eats and has expanded into freight and other logistics sectors.

Both Hart and Cuban admit that turning down Uber is a decision they’ll always consider. Uber’s success shows that even the craziest ideas can become huge. “Don’t feel bad,” said Cuban. Still, Hart admitted that “Until this day, I think about it. Until this f***ing day. You know. I kind of avoid seeing Troy Carter, too.”

Of course, there are countless examples of great ideas being turned down by numerous investors. For example, in 2000, Reed Hastings, the co-founder of Netflix, approached Blockbuster with an offer to sell Netflix for $50 million. Blockbuster declined, not seeing the potential in a DVD-by-mail service.

In its early days, Airbnb struggled to find investors who believed in people renting out their homes to strangers. Many saw it as a risky and unprofitable venture. Today, Airbnb is valued at $75 billion.

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