The Maverick Billionaire

Mark Cuban—Shark Tank star, NBA franchise owner, social media maestro—is having a lot of fun, and he’s taking the rest of us along for the ride.

- Bill Saporito

It was all working according to plan for Mark Cuban. He had sold his first business, Micro Solutions, in 1990, retiring handsomely rich at age 29. He bought a lifetime, fly-anywhere-with-a-friend forever pass from American Airlines and had envisioned an immediate future of reasonable if dedicated debauchery. The plane-and-party proposition gained some altitude, but as sometimes happens, a woman kept diverting him back to his adopted hometown of Dallas.

“I was having a blast. But there is always that girl who gets in the way,” Cuban told me via email, a medium in which he is famously responsive. Pity that romance didn’t work out, but then again, spending more time in Big D to be near “that girl” would lead to him co-founding, with Todd Wagner, Audionet in 1995, just as something called the Internet was catching on.

Cuban took Audionet—later renamed Broadcast.com—public in 1998, and a year later sold the company to Yahoo at the peak of the dot-com frenzy for about $5.6 billion. He netted some $1.3 billion. “We are still friends,” he says of that lost love. “But don’t tell her about this!”

Today, the 58-year-old Cuban is having more fun—and continues to make more money—than the rest of us, but at least he’s happy to let us go along for the ride with him. He’s the people’s billionaire: the fanboy owner of the Dallas Mavericks who turned a broken franchise into an NBA champion; a Shark Tank megastar with a portfolio of investments in companies whose products he sells as part of his own Amazon collection.