An illustration of a man smiling on a brightly colored background

Illustration by Frank Stockton

Mark Cuban is arguably the hardest working billionaire out there. Once people amass that much wealth, they may want to camp out on a gigayacht or, say, endlessly fart around with the social media platform they overpaid for. But not Cuban, owner of the Dallas Mavericks basketball team and one of the stars and executive producers of the entrepreneurial reality show Shark Tank. Cuban is addicted to the grind. To wit, he insisted on conducting this interview over email, and after I sent him my first round of questions at 10:49 p.m., he replied the next morning at 7:55 a.m.

“I do most of my work like this, on email,” writes Cuban, whose Gmail address is readily available if you Google it. “I get 500 to 1k a day, so that is most of my day!!” (I’ll spare you the exclamation points in the interview, but let’s just say he’s enthusiastic.)

Cuban arrived in Dallas in a Fiat with “a hole in the floorboard” in the summer of 1982, after graduating from business school at Indiana University. He wanted to live someplace warm where he had friends. He moved into a three-bedroom apartment with five buddies. “It was ugly lol,” he writes. He began working at a software company, where he was quickly fired. Undeterred, Cuban started MicroSolutions, a computer consulting business he sold to CompuServe for $6 million in 1990. Nine years later, he sold, an audio streaming service, to Yahoo for $5.6 billion.

Cuban has the golden touch. His team has won an NBA Championship and his show multiple Emmy Awards, while his ever-expanding portfolio includes more than 200 companies. Still, his biggest challenge might lie ahead: building a Mavericks squad around superstar Luka Dončić to keep him from leaving for free agency. But sports is a business, and we know Cuban’s business record.

TH: When did you realize you wanted to be a businessman?
MC: When I was about 9. I was selling baseball cards to friends. By 12, I was selling garbage bags door to door. I started to get my confidence and that got me reading about business, which confirmed to me that I was an entrepreneur.

TH: Who inspired your trajectory in life?
MC: My dad. He did upholstery on cars and never went to college. But he always inspired me to focus on learning and be curious about business. No matter how much I struggled, he always supported and encouraged me.

TH: Is Texas a good place for entrepreneurs?
MC: It’s a great place for entrepreneurs. It’s very business friendly. It’s got a great energy and people willing to learn and work hard. Which is exactly why I have stuck with Dallas. What makes it special is the can-do attitude of people here. We are a state full of people who are working toward their own American dream, and we support entrepreneurs. Which makes Texas a great place to start a business.

TH: What do you like to do for fun?
MC: Play basketball, work out, walk the Katy Trail, and read. Right now, I’m focused on learning as much as I can about large language models [artificial intelligence algorithms]. So I’m on reading all their tech articles.

TH: Where do you like to eat?
MC: Wherever my teenagers want us to go. Usually it’s Rise, a restaurant with amazing soufflés.

TH: What other places in Texas have you visited that you’ve enjoyed?
MC: Love Austin—great music and tech scene. Houston is great, and the River Walk [in San Antonio] is still amazing. But Texas needs a destination that every family outside of Texas wants to vacation and see, that every conference wants to experience. That is the biggest economic opportunity the state has: to become a tourist destination for the country and the world. My hope is the state will enable resort destinations with gaming support. I think it would make Texas the number one tourism destination in the country.

TH: Shark Tank is heading into its 15th season. What makes it a successful show?
MC: It’s that we send the message that the American dream is alive and well. That anyone from any town across the country can start up a business and grow it into something special. There is no other country in the world that is anything like the USA for startups. Shark Tank inspires people to go for it.

TH: Tell me about a Texan from the show who you’ve gone on to have a successful business relationship with.
MC: Wondry Wines is a Dallas-based winery that is crushing it. They embody what makes a great company. They have great products, entrepreneurs who work their asses off daily, and they are always working to improve at every level.

TH: What inspired you to start your pharmaceutical company Cost Plus Drugs?
MC: The health care system in this country is a mess. The idea that people can’t afford their meds or have to choose between food, shelter, and medication is insane. Our hope is that Cost Plus Drugs can change that. We measure success by the number of people we can help save on their medications, and so far that number is fast growing well into the millions. We will keep on pushing to expand the medications we offer and continue to always make sure we are completely transparent with our pricing.

TH: A couple of years ago you talked about a potential run for president. What happened?
MC: My family didn’t want to go through it. They voted me down. Seeing how politics works, I’m glad they did.

TH: The press has quoted you as saying, “Call me woke.” What did you mean?
MC: I think it’s good business to share the values of and find similarities with all your customers and prospects, and the more diverse your prospect base, the more opportunities a business has to be successful. Being nice and considerate to everyone is always a plus, and if that’s called “woke,” I’m good with that.

TH: What prompted you to make the comment?
MC: I was tired of everyone using the line “Go Woke Go Broke.” It’s just not true. Treating everyone with respect is always good business.

TH: You like to mess with Elon Musk on Twitter. Why?
MC: Why not?

TH: What’s your take on Musk?
MC: I think he is great for business in Texas. He keeps growing his companies here, and I don’t care about his image.

TH: You purchased the Dallas Mavericks in 2000. How would you evaluate that acquisition?
MC: When we win it’s fun. When we don’t win, not as much [insert smiley face emoji]. But I love the Mavs and the sport.

TH: What can you do as the owner to ensure Luka Dončić stays and to get the team back to championship-caliber basketball?
MC: Win a lot of games. Do we win or not? That’s what matters to me.


The new season of Shark Tank begins in September. The Dallas Mavericks tip off the 2023-24 season in October. For more about Mark Cuban’s businesses, visit

From the September 2023 issue

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