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Think you know Mark Cuban? Our podcast shows a different side of a shark

Mark Cuban: NBA owner, "Shark Tank" investor, and one very emotional guy. He lets it all hang out in the latest episode of “Life in Seven Songs.”

Four men are smiling and posing for a group photo. Two wear black bow ties, one wears a red bow tie, and there is a drink in hand. They seem happy and festive.
Mark Cuban, bottom left, and roommates partying at a bar in Dallas in the 80s. | Source: Mark Cuban

The people closest to Mark Cuban might not be surprised to learn that the billionaire entrepreneur is a big fan of Wild Cherry’s 1976 hit “Play That Funky Music.” But they probably couldn’t guess the reason. The story of Cuban’s white-boy funk fandom — and other private moments he reveals in the latest episode of The Standard’s “Life in Seven Songs” podcast — show sides of him that most haven’t seen. 

There’s the funk-loving Cuban. The emotional, sentimental Cuban. The Ponzi-scheming Cuban. And the relentlessly optimistic Cuban.

As he transitions away from the two arenas where he made his name over the last two decades — “Shark Tank” and the Dallas Mavericks — Cuban reflects on the many lives he has lived. Here are a few things listeners will learn from his life journey.

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He started a pyramid scheme to pay for his college tuition

His father was an automobile upholsterer who passed him the occasional 20-spot but otherwise paid for little, leading Cuban to develop a shrewd business sense. In his junior year of college, Cuban created a chain letter asking fellow students for $100 and promising a return on their investment down the line — an ersatz Ponzi scheme. “It was basically a scam,” he said. It was also how he paid his way through school. 

Three men pose playfully against a wall with musical notes and names painted on it. They're standing closely, with casual outfits, in a dimly lit room.
After paying for college with a chain letter scheme, Cuban bought a bar with friends and named it Motley's Pub. | Source: Mark Cuban

Before making his first million, he was sleeping on the floor

Cuban moved to Dallas in 1982 for what he thought would be a quick stint. Sleeping on the floor of a five-person apartment he referred to as “the shithole,” he began working in software sales. But after a big sale that landed him $1,500 in commission — enough to move out of the shithole — he was fired. He started a company called MicroSolutions and later sold it for $6 million.

He is never going to stop selling 

Last year, Cuban sold his majority stake in the Dallas Mavericks. This year, “Shark Tank,” on which he has starred since 2011, has its final season. But Cuban has no plans to retire. His latest venture, the discount company Cost Plus Drugs, aims to fight back against Big Pharma and Big Drugstore. 

“I’m the luckiest guy in the world,” he says. “People are like, ‘You’re wealthy, why are you still doing business? Why aren’t you on a boat somewhere?’” His response? “I love doing this.”

Listen to Cuban’s playlist on Spotify and find a transcript of the podcast episode here. Thoughts? Guest suggestions? Email us at lifeinsevensongs@sfstandard.com.