Billionaire Mark Cuban Used to Sleep on the Floor And Wear 2 For $99 Polyester Suits In His 20s—Now He Says Confidence Beats Trying to Look 'Fancy'

Mark Cuban didn't grow up with a trust fund or an Ivy League name to flash around boardrooms. He was the Pittsburgh kid selling garbage bags at 12 just to buy sneakers. By his 20s, he was living in Dallas, driving a beat-up Fiat with a hole in the floor, sleeping on the floor of a crowded apartment, and wearing "2-for-$99 polyester suits." Not exactly the "fancy" setup you'd expect from a future billionaire.

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But according to a Fireside Chat with author Chris Voss in 2023, that humble start came with something else: insecurity.

"I didn't have anything fancy about me… it was kind of like impostor syndrome—that I had to push hard to prove that I knew my stuff," Cuban said.

That pressure to prove himself? It backfired. "Early on in my career, I wanted to prove how smart I was and so I did a lot more talking than listening," he admitted. His need to sound like the smartest guy in the room sometimes led to what he now calls being "too cocky."

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The consequences weren't just awkward meetings. Cuban shared that his cockiness carried into deals—like the time he sued DirecTV in 2007 over a dispute with his network HDNet. "I was arrogant, and I didn't respect them as much as I should've," he said. The legal battle? "It cost me more money than the deal was worth."

Cuban's career eventually skyrocketed—he sold MicroSolutions for $6 million and later Broadcast.com to Yahoo! for $5.7 billion—but the early lessons stuck. These days, he plays it differently.

"One of the best negotiation strategies is to just be quiet and listen," he told Voss. And more importantly? "If I had to do it again, I think I would have been a little bit more confident and not as concerned that people weren't taking me seriously."

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Now, he leans into preparation instead of posturing. "I'd have more confidence in my preparation than I did then," he said.

Bottom line: Cuban didn't have the pedigree, the suit, or the car—but what he lacked in polish, he made up for in hustle. And if he could give his 20-something self advice? Stop trying to impress people. Just do the work.

Now? He's worth billions…and still doesn't care if you think he's fancy.

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