On his first big exit, he bought himself not a hot car nor a bigger house, but a lifetime pass on American Airlines (since discontinued) that gave unlimited flights for him and a guest, in first class, for the rest of his life. He still carries the card "to remind me to party like a rock star," even though he transfered the actual benefit to his dad. In fact, he explained that if two first-class seats weren't available on a flight Cuban wanted to take, the airline would actually bump someone — and one day that poor soul happened to be Magic Johnson. "So yeah," he said with a big grin, to howls of laugher, "that was fun."
Advice continued about scaling your company, how to iterate on ideas, developing a company's culture, and why Googling to see if your idea is unique doesn't work. (Because Google won't find all the failed iterations that aren't online anymore, of course.) Cuban explained that the NBA is wrong about its business — it's not selling basketball, it's selling a unique experience, the energy and emotional roller coaster of live sports you can't get anywhere else. He swore the rumor about him paying fines to the commissioner with truckloads of pennies was false, but the story about him matching every fine with a charitable donation is true.
Everyone wanted to hear about Shark Tank, the ABC reality program in which would-be start-ups try to get Cuban or four other entrepreneurs to fund their ambitions. One of the entrepreneurs in attendance Sunday had actually been on the show — Cuban didn't invest, so we all had a good giggle about that, although the man's business, a chain of fast-casual, custom sushi restaurants called How Do You Roll?, is still doing incredibly well. Cuban swore nothing on the show is fixed, and he loves the ones that are clearly scams: "Knowing it's going to be edited way down, I'll rail into them, like, F*** you, there's no way!'"
When it was time for Q&A, the audience was warned not to ask silly questions (some were still sillier than others), and not to pitch. Do not pitch Mark Cuban! But then he paused to pitch us, on his new Snapchat-like app for disappearing messages, called Cyber Dust. Kids are starting to understand that everything you do on sites like Facebook and Twitter are added to your permanent digital record, as it were, later used to sell you things — hence the popularity of Snapchat, according to Cuban. And he's trying to reduce his own digital footprint, too, since the further you get from any one communication, the less context it has, and then later on the SEC or someone who's suing you could interpret that communication in ways you might not have intended. And since he's Mark Cuban, no one ever deletes his texts — billionaire problems, for sure, but it does make sense.
Sign up for CIO Asia eNewsletters.