Before Mark Cuban became a billionaire, a TV fixture, and a guy who casually disrupts Big Pharma for fun, he was just another confident tech founder trying to make it in the ‘80s. He had a million-dollar company, a little swagger, and—at least for one night in Las Vegas—a front-row seat to what happens when Bill Gates walks into a bar.
It all came up during a 2022 episode of the “Full Send Podcast”, after the hosts asked Cuban about competition and missed opportunities. That’s when he lit up with:
“I’ll tell you a story. I’ll tell you a story about in Vegas back in the day about Bill Gates.”
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This wasn’t just any Vegas story—it was COMDEX, one of the biggest tech trade shows in the world at the time. According to Cuban, the crowd was massive. “125,000 people,” he said. “I started my company, I was like 26, 27… and I just thought I was a badass.”
He was feeling good, hanging with a group of women, ordering shots, and assuming the night was going his way.
“This was right when Microsoft had gone public,” he said. “So one day, no one knows who Bill Gates is. The next day, he’s the king of tech.”
That’s when the girls told him they needed to run to the bathroom—and never returned.
“I’m like, what the f***?” Cuban said, still laughing about it decades later.
His buddy leaned over and broke the news: “Yo, do you know who Bill Gates is?”
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Turns out Gates had just hit a net worth of around $350 million. Cuban? “I was maybe worth a million dollars.” Which made him… invisible.
“Bill Gates took my girls!” he admitted, laughing. But the sting was real.
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The host cut in: “Did that fire you up? That should’ve motivated you, right?”
“It did motivate me,” Cuban shot back. “Right? To find—to go on to the next…”
Years later, Cuban finally got a chance to one-up the tech legend. After selling Broadcast.com, he was invited to speak at a conference. The organizers mentioned Gates would be speaking first.
“I’m like, the only reason I’m doing this is because Bill Gates is talking right before me,” he said.
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So when it was his turn, he walked out on stage and delivered the zinger he’d probably been waiting years to say:
“I’m excited to tell you I sold my company… and finally, after all these years, Bill Gates is my opening act.”
Cuban says Gates “got so pissed.” And the kicker?
“I’ve never talked to him since,” Cuban said. “Not to this day.”
Not out of spite. “Not that I’ve had any reason to talk to him,” he added. But that night in Vegas? Still a core memory.
He may have lost the girls, but Cuban got the punchline. And maybe a little satisfaction knowing that even tech royalty doesn’t always get the last word.
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