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Mark Cuban on the biggest career regret from his 20s—what he’d change if he could ‘do it again’

Mark Cuban has some regrets from his early days.

In a Q&A session with best-selling author Chris Voss on Fireside, a streaming platform that Cuban co-founded, the Dallas Mavericks owner said his early-career impostor syndrome often led him to overcompensate in business meetings and negotiations.

Earlier in the conversation, Cuban had touted that one of his current negotiation strategies is to “just be quiet and listen.” He said that tactic gives him time to gather information about a potential deal.

But Cuban learned that trick the hard way.

“Early on in my career, I wanted to prove how smart I was and so I did a lot more talking than listening,” Cuban said.

He explained that when he was just getting started, he was self-conscious about often being the youngest entrepreneur in a room and not having “the pedigree” of some of his peers. At the time, Cuban says he was sleeping on the floor of a three-bedroom apartment with six roommates in Dallas. He had recently been fired from his software job and wanted to start his own business.

Cuban founded his first company, MicroSolutions, while still in his 20s before eventually selling it to CompuServe for $6 million in 1990.

“I didn’t have anything fancy about me. I had the 2-for-99-dollar polyester suits. And so I always felt that — it was kind of like impostor syndrome — that I had to push hard to prove that I knew my stuff,” Cuban said.

The desire to prove himself sometimes led Cuban to be “too cocky,” he says, which could rub people the wrong way. It also continued getting him into tough situations well after his career took off.

For example, Cuban cited a 2007 incident when negotiations soured between him and DirecTV. The cable services company wanted to move Cuban’s company HDNet, a high-definition TV provider, to a higher price tier. Cuban didn’t like the deal and consequently sued DirecTV.

“I was arrogant, and I didn’t respect them as much as I should’ve,” Cuban said. “That was an enormous mistake.”

Eventually, they settled the lawsuit, and he says that while he did secure a more favorable arrangement with DirecTV, it wasn’t really worth the legal battle: “It cost me more money than the deal was worth.”

Today, the billionaire investor’s fiery temperament occasionally still causes him headaches. In 2020, for instance, the National Basketball Associated slapped Cuban with a $500,000 fine for public criticisms of NBA officials after the Mavericks lost to the Atlanta Hawks.

Even so, Cuban says that his early-career mistakes have made him more careful about getting caught up in lawsuits: “You can always negotiate your way out if you’re being honest and fair.”

In retrospect, Cuban says those early missteps might have been avoided if he had been less worried about what people thought of him.

“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,” Cuban said.

He has learned that there may always be someone in a negotiation who does not see you as legitimate. Instead of paying attention to those voices, Cuban suggests leaning into preparation.

“Now if I went back to do it again, I’d have more confidence in my preparation than I did then,” he said.

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