The regret of missing a good deal can go as far as fifteen years, as Billionaire Mark Cuban who turned down investment in Uber in 2009 still feels sad for his decision. During that time, he was asked to invest $250,000 investment in Uber, had it been done at that time, Cuban would have owned stake worth ₹$2.3 billion in the company.

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He was approached by Uber cofounder Travis Kalanick about making investment in Uber at a valuation of $10 million. Currently, the company's market capitalisation stands at about $ 90 billion.

In the recent episode of Heart to Heart, Kevin Hart's talk show on the Peacock, Mark Cuban again mentioned his decision and regretted. “I said, ‘I’ll do it at $5 million valuation,’" the Shark Tank star recalled, reported Fortune's Steve Mollman.

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He was apprehensive that the regulatory pain faced by the Uber will hinder its progress. He also warned Kalanick that taxi commissions would “try to put you out of business," reported the website.

By the time of pitching the ‘Uber’ idea, Cuban and Kalanick had already shared the relationship of an investor and startup oowner. In 2005, Cuban had invested $1.7 million in Kalanick's previous venture, which was a peer-to-peer networking startup called Red Swoosh, reported CNBC. After the startup was sold to cloud services company Akamai in 2005, Cuban managed to make decent money.

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He was pretty impressed with the idea of Uber services. “He comes to me, like, first off [and says]: ’I’ve got this thing. It’s going to replace taxi cabs..." Cuban recalled. “I was like, ‘I love it,’ " reported CNBC.

The main bone of contention was the valuation of the startup. Cuban didn't agree with Kalanick’s $10 million valuation of the startup at the time. After that Kalanick never returned to Cuban for investment.

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