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."
Uber, though currently struggling with accusations of gender bias and sexual harassment, has been a tremendous Silicon Valley growth story. Founded in 2009 in San Francisco, the transportation technology company is currently operating in almost 600 cities across the world. It has raised almost $9 billion and is valued at $66 billion.
"The point is, when you are trying to disrupt something like Travis was doing," says Cuban, "sometimes you have got to be ready, fire, aim and just bust through doors and figure you will deal with the regulatory issues later."
The billionaire tech investor and owner of the Dallas Mavericks acknowledges that he had reason to hesitating. Uber is facing some challenges for launching in markets before getting proper approvals. In particular, Uber has admitted to "greyballing," or using a technical problem to hide from local regulators in cities where the service was not approved by local regulators, like Portland, Oregon. And Uber hasn't functioned in Austin since May 2016.
Still, Cuban's main takeaway is that he should have been thinking bigger. Kalanick "has obviously disrupted transportation, and he's trying to do a whole lot more than that, and he gets all the credit because where I saw regulation, he ignored it," says Cuban.
"If you really believe and you really have something that you think is going to disrupt the world, bring it to me. I won't make the same mistake twice, and then just go and bust through those doors and figure out how to get through the hurdles."
Cuban says he should have known better than to doubt that Kalanick could overcome regulatory hurdles, because that's what Kalanick did when he launched his first tech company.
"When we started in the streaming industry, there were so many rules about what you couldn't do in terms of content and broadcasting TV and copyright laws and this and that and we just ignored them. We rather ask for forgiveness than come out and get approval in advance and it turned out for us then, too," says Cuban.
He and Todd Wagner launched the internet start-up Broadcast.com and sold it to Yahoo for $5.7 billion in 1999.
"I should have learned by lesson," says Cuban.