Kevin Hart and billionaire investor Mark Cuban have one major regret in common: 

They both passed on the chance to invest in Uber UBER  when it was just getting started. And looking at Uber today, that decision still stings.

On an episode of Hart to Heart, Kevin Hart's talk show, the two shared how they let the opportunity slip away. Back then, the idea of strangers hopping into cars with other strangers seemed like a disaster waiting to happen. Hart even called it “Murderville,” thinking it was the dumbest idea he'd ever heard. 

Cuban, on the other hand, was actually interested—but only if he could invest at a lower price. When his offer wasn't accepted, he walked away.

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Troy Carter, a former music manager turned tech investor, was the one who first pitched Uber to Hart. He told him, “There’s this thing, man. It’s called Uber. You got to invest in it.” But Hart just couldn't see the potential even after Carter further explained the concept: “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.” “Sounds like Murderville to me. This has to be the stupidest shit I ever heard,” he told Carter.

Fast forward to today, and Uber is a massive success. In the third quarter of 2024, the company reported $11.19 billion in revenue, up 20% from 2023. Uber's Gross Bookings hit $40.97 billion, a 16% year-over-year jump, and ride-hailing bookings rose 17% to $21 billion.

Uber also does more than simple rides nowadays—it dominates food delivery through Uber Eats and has expanded into freight and logistics. 

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Hart and Cuban admit that turning down Uber was a tough lesson. “Don't feel bad,” Cuban told Hart, but Hart still thinks about it. “Until this f***ing day,” he admitted, adding that he kind of avoids running into Carter because of it.

Of course, they're not the only ones who've let billion-dollar opportunities slip away. In 2000, Netflix NFLX co-founder Reed Hastings offered to sell the company to Blockbuster for just $50 million. Blockbuster passed, failing to see the future of streaming. Airbnb ABNB also struggled early on, with many investors doubting that people would rent their homes to strangers. Today, Airbnb is valued at around $82 billion. In fact, here are simple steps on how you, too, can invest in this company. 

The lesson? Some of the wildest ideas turn into industry giants. Even the best investors don't always get it right.

Disclaimer: Some elements of this story were previously reported by Benzinga and it has been updated.

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