Cuban invested in Uber CEO Travis Kalanick's first start-up, Red Swoosh, a peer-to-peer file sharing company. When Kalanick had the idea for Uber, which he first called Uber Cab, he sent an email to Cuban pitching the idea and seeking funds.
Cuban liked the idea but had reservations. "You are going to have to fight all the taxi associations, and all the transportation organizations in each city and every state," says Cuban. "Then I started talking to him about his valuation, and I never heard back from him. The rest is history."