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Kevin Hart had a shot at Uber for $50,000 to $75,000. He passed because it sounded “like murderville.” Uber went public at $82 billion. Mark Cuban passed too, and he knew the founder. In the video below, Hart and Cuban take turns telling how each of them missed Uber. Music executive Troy Carter pitched it to Hart. There’s an app. You need a ride, and a stranger nearby comes and picks you up. “Sounds like murderville to me,” Hart told him. “I don’t know that person. I ain’t picking them up.” Years earlier, Cuban had rescued Travis Kalanick’s first company when it was running out of money. Then Kalanick came to him with something called UberCab, at a $10 million valuation. Cuban loved it. “I’ll do it at $5 million,” he said. Kalanick found someone else and never came back. In fairness to both men: in 2010, getting into a stranger’s car did sound insane. And Cuban’s warning was right. He told Kalanick the taxi commissions would fight to put him out of business. They did, and Uber didn’t post a full year of operating profit until 2023. Cuban was right about everything except the ending. He shrugs it off. “I’ve done okay.” Hart can’t. “Until this day, I think about it,” he says. “I kind of avoid seeing Troy Carter.” On the Street, the deal that sounds stupid in the room is the only one nobody else is bidding on. Would you have put $75,000 into riding with strangers in 2010, or said what Kevin Hart said?