The focus of Mark Cuban’s Q&A at South by Southwest was supposed to be about government disruption, and he was supposed to hype up the Austin-based insurance company The Zebra, one of his newest investments. But Cuban, everyone’s favorite love-to-hate billionaire entrepreneur and Shark Tank star, had a few other topics in mind. You might say that the charismatic Cuban disrupted his own session. Here are the five standout anecdotes, stories, and lessons he decided to share. 

President Trump is tech illiterate, and Cuban has stories to prove it

Cuban hates when people compare him to President Trump, but it’s easy to see why they do—they are both wealthy businessmen with reality TV shows. According to Cuban, even Trump thinks they’re alike—“[He] says we’re like the Bobbsey Twins,” Cuban said—but he wants the comparisons to stop there. He told stories about Trump’s lack of basic tech skills, detailing Trump’s preferred way to respond to Cuban’s emails. 

“His assistant would print it out, he’d write his responses on the copy, and then his assistant would send it back to me as an email attachment.”

Another thing Trump apparently doesn’t know how to do? Use Google.

“Just think how much safer our world would be if our president learned how to use a search engine,” Cuban said. 

Uber is successful because they ignored the rules 

Several years ago, Cuban received a pitch from a young Travis Kalanick about a new taxi-like service called UberCab. Cuban thought it would never work—there were too many hoops to jump through involving the rules and regulations of the taxi industry. 

“Where I saw regulation, Travis ignored it completely,” Cuban said. 

The rest, of course, is history. Uber forged ahead and has forced many major cities to rethink its regulations as a result. Now, Cuban advises other entrepreneurs to be less concerned about the rules if they have a strong enough idea. 



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