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What I learned from a shoeless Mark Cuban at SXSW

AUSTIN—The One World Theatre is not a typical South by Southwest venue. It sits high on a hill northwest of town, about nine miles from the convention center, with beautiful views and none of the overcrowded messiness of the show itself. On Saturday, Dallas Mavericks owner and Shark Tank star Mark Cuban spoke to about 300 entrepreneurs here—members and guests of Entrepreneurs Organization’s Austin branch. Tagging along were a few lucky members of the media—including me.

To join EO, your company must be raking in at least $1 million in revenue, so I suddenly found myself surrounded by well-dressed, well-connected go-getters in fancy shoes, mingling and networking while waiting to pick the brain of one of America’s most charismatic billionaires. I rolled up in a hotel shuttle van, wearing dirty, fake-leather boots and a giant backpack of phone chargers and miscellaneous swag—the only person wearing a SXSW badge, my event nametag handwritten with Sharpie instead of laser-printed, my thrifted jacket soggy with the rain that had pelted downtown’s festival grounds all morning.

Strangely, it wasn’t raining on the hill.

The millionaires were definitely nice people, but a couple things made it weird from the get-go: The only other attendee who spoke to me during the cocktail hour was a fellow journalist wearing flowered Doc Martens (holla, Veronica!), and when I stepped up to the bar I was shocked to be charged $2 for a bottle of water. (Granted, you don’t get rich by giving away water.) The sushi and dessert buffets were free, though. Go figure.

Once inside the theater (sorry, theatre), I pulled my laptop and camera out of my giant backpack to document the proceedings, and the friendly guy to my right quipped, “Are you working?!” When I confirmed that I was, he laughed, “I guess someone’s got to! Better you than me!” Indeed. (I always assumed running a company was a lot of work, but he didn’t seem stressed, God bless him.)

I did exhale a bit when Cuban sauntered on stage wearing a T-shirt and jeans, sank into a huge, bright red, unapologetically modern armchair, and immediately kicked off his sneakers. (Blindingly white socks with NBA logos, to answer the question I’m sure is on your mind.) I no longer felt grossly underdressed. Cuban’s interviewer, EO Austin president Dustin Wells (and also the founder and CEO of Headspring), ditched his fancy leather loafers as well. Then all Wells had to do was wind Cuban up and watch him go.

cuban sxsw

A shoeless Mark Cuban fields questions at a South by Southwest event sponsored by Entrepreneurs Organization, which probably has more stringent footwear requirements most of the time.

Cuban’s talk was hilarious, as he peppered his entrepreneurial advice with stories from his life, starting back when he was 12 and got his first job from his dad’s poker buddy selling trash bags door-to-door for a $3 markup. He had the crowd rolling with his wisdom on how to spot a gold digger (she’ll say she loves travel and charity work), and how he knew he needed HR people at one of his early companies (when a service woman “wanted to sleep with everybody in the service department in the same night—who the hell does that?”).

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.

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Mark Cuban (top row, center) in his natural, shark-infested environment

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!’”

cyberdust

Cyber Dust is a Mark Cuban-backed app that will remind a lot of people about Snapchat.

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.

But whether you happen to be a billionaire, a millionaire, or even a soggy-jacketed five-figure-aire like myself, anyone can appreciate Cuban’s universal advice for living: Be grateful. Keep hustling. Treat everyone with respect. “And don’t forget to have fun.” I know I did.

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