Confessions of a Billionaire: Real Talk With Mark Cuban

Confessions of a Billionaire: Real Talk With Mark Cuban

By James Watkins


Because it’s Mark friggin’ Cuban.

By James Watkins

“If he lasts four years, I’ll be there to kick his ass.” The famously brash billionaire whose favorite pastime is to drop hints about running for office was speaking about someone who just three years ago was in the same position. And, like the president, Mark Cuban doesn’t pull his punches.

“I was the class fuckup,” he told the audience at yesterday’s OZY Fest in New York’s Central Park, while trading blows with comedian Samantha Bee and former governor Jeb Bush in a discussion about education policy. The 58-year-old businessman and investor turned “shark” on ABC’s Emmy-winning investment reality show Shark Tank started out selling garbage bags as a 12-year-old to pay for a pair of expensive basketball shoes. A software startup, some canny investment decisions and a few decades later, Cuban now has access to all the basketball merchandise he wants as the owner of the Dallas Mavericks and a Forbes-estimated net worth of $3.4 billion.

We caught up with one of the country’s most successful entrepreneurs before he walked on stage at OZY Fest — to get his take on everything from how to pitch the Sharks to how sports team ownership has changed. This interview has been condensed and edited for clarity. 

Mark Cuban w/Carlos Watson

Mark Cuban goes one-on-one with OZY Editor-in-Chief Carlos Watson at OZY Fest.

Source Brad Barket / Getty

What lessons from business apply to sports?

Mark Cuban: Business is the ultimate sport. You’re competing not only with the competition you know but also the competition that hasn’t even been invented yet. Particularly in technology, there’s always some 12-year-old boy or girl that’s out there trying to kick your ass. So you have to always stay ahead, it’s always changing.

I tell our [Mavericks] players, they have to practice an hour or two, they play their games, 48 minutes, then they get to sleep. In business it’s nonstop. It’s always on, and it’s the most competitive sport there is.

And what about lessons that apply to politics?

Cuban: Politics right now is a little bit different from business. Business is about results, but politics is about perceptions. So I think it’s difficult for a true businessperson to go into politics because they’re really results-oriented. You see that right now — the Republicans do what the Republicans think; the Democrats do what the Democrats think. I just think it’s difficult.

What expertise transcends the different industries you’ve worked and invested in, from tech to sports, entertainment and others?

Cuban: The one thing that transcends all industries is effort, and the willingness and desire to learn, because every industry changes constantly. Learning is a skill that’s required no matter what business you’re in.

We’re going through a transition right now with artificial intelligence, machine learning, neural networks, deep learning, where companies are going to have to adjust, to learn how to acquire data and use that data in ways they never have before. We’re going through a transitional period where we’ll see more disruption driven by artificial intelligence than we’ve seen in the last 30 years.

I liked it better when I was just pissing everybody off, but now I piss people off and they expect it.

Mark Cuban

What is the hallmark of success that you look for in a pitch? And what is the biggest red flag?

Cuban: Confidence, preparation and vision. I can just tell when someone’s committed. When you’re in, you’ve got to be all in. Because there’s so much uncertainty, you’ve got to be willing to put in the effort to learn what it takes to win.

The biggest red flag is not being able to give a direct answer. When someone talks around the question, instead of saying what they did wrong. You can’t do that in business. You have to be able to give a direct answer, even if that’s just saying “I don’t know.”


What has been your biggest failure?

Cuban: Oh my goodness, I have so many! The guy who started Uber, I funded his last business. And when he started Uber, I was like, “I like the idea, but let’s talk about how you’re going to do this.” He went ahead and did it anyway.

But it doesn’t matter how many times you fail, you’ve just got to get it right one time. That’s all it takes.

Do you think your hands-on approach has changed the role of sports owners?

Cuban: Oh yeah. When I first bought the Mavs, everyone was like, “Get the hell out of there, that’s not what you’re supposed to do.” Now, fans, players and organizations all expect hands-on owners. They expect someone who knows what’s going on, not just a delegator. It’s not a toy anymore, it’s a business.

What is it like to be one of the veteran NBA owners now versus a young “disrupter”?

Cuban: It’s weird. I hate it. I keep looking in the mirror, and those wrinkles keep showing up! I liked it better when I was just pissing everybody off, but now I piss people off and they expect it. It was more fun when I was the young guy.

Tell us about a rising star whom we should watch out for in the next couple of years.

Cuban: Dennis Smith Jr, a Mavericks draft pick. He’s got unbelievable potential.

What about an important trend you have your eye on?

Cuban: Without question, machine learning, computer vision and neural networks are changing everything. It will change how people approach problem-solving and how businesses approach everything. There’s a downside too — a lot of jobs that were very repetitive are going to get replaced by neural networks.

What’s one piece of Good Sh*t you’re obsessed with and want to recommend to the OZY audience?

Cuban: I just finished a book I loved, The Master Algorithm, by Pedro Domingos. It’s not quite a beginner’s guide, but it’s a guide to artificial intelligence, to help you understand what’s going on.

Finally, tell us a fun fact about yourself that other people don’t know.

Cuban: I played rugby for 15 years. I’m terrified of heights. And I’m trying to learn the piano.