Long before Mark Cuban became a billionaire entrepreneur, NBA team owner, and household name on Shark Tank, he was just a broke 24-year-old college grad with a hustle — and a handful of powdered milk packets. In a recent episode of the “Aspire” podcast hosted by Emma Grede, Cuban revealed how his very first business venture — selling powdered milk — failed spectacularly in just 30 days.
Armed with under $20 and unshakable optimism, Cuban believed his budget milk substitute could revolutionize frugal kitchens. “I remember taking samples to people, mixing it up, like, ‘Look, milk’s expensive. We’re broke, right? This will save you money,’” he said on the show. The response? Indifference at best, revulsion at worst.
That sting of rejection might have ended the story for most — but for Cuban, it was just the first step.
What Failing Taught Him
The powdered milk venture was Cuban’s crash course in entrepreneurship. “It did not sell,” he admitted plainly. But that 30-day loss proved to be a long-term gain. “It doesn’t matter how many times you fail. You only have to be right one time,” he reflected.
And he was. Shortly after, Cuban launched MicroSolutions, a software reseller company. With no outside funding and no time off (“I didn’t take a vacation for the next seven years,” he told The Playbook by Entrepreneur), Cuban hustled his way into profitability. By 1990, he sold MicroSolutions to CompuServe for $6 million. Nine years later, he made internet history by selling Broadcast.com to Yahoo for $6 billion.
From Sleeping on Floors to Owning the Dallas Mavericks
Cuban's early struggles were far from glamorous. He was fired from a computer store, lived with six roommates in a cramped apartment, and often slept on the floor. But instead of retreating, he went all in — and stayed all in.
“There is no balance,” Cuban once told Sports Illustrated. “If you want to crush the game, whatever game you’re in, there’s somebody working 24 hours a day to kick your a*s.”.
Sweat Equity Over Start-Up Capital
What if you’re starting with nothing today? Cuban says the answer lies not in bank accounts, but in sweat equity. If he had to build from scratch in 2025, he’d lean into artificial intelligence — and not by spending, but by learning.
“I’d be all about AI,” he said. “If I had access to a library and $0, I’d be in there till they kicked me out.” He suggests learning to prompt AI tools effectively, then offering services to small businesses to improve efficiency. In other words: find a skill, sharpen it for free, and sell it.
Despite his massive fortune (estimated at $6 billion, per Forbes), Cuban’s proudest achievement might just be the control he now exercises over his own time. At SXSW 2024, he shared a telling anecdote — after making his first million, he threw away his watch. “I didn’t want to respond to anyone else,” he said. “I wanted to own my time.”
Armed with under $20 and unshakable optimism, Cuban believed his budget milk substitute could revolutionize frugal kitchens. “I remember taking samples to people, mixing it up, like, ‘Look, milk’s expensive. We’re broke, right? This will save you money,’” he said on the show. The response? Indifference at best, revulsion at worst.
That sting of rejection might have ended the story for most — but for Cuban, it was just the first step.
What Failing Taught Him
The powdered milk venture was Cuban’s crash course in entrepreneurship. “It did not sell,” he admitted plainly. But that 30-day loss proved to be a long-term gain. “It doesn’t matter how many times you fail. You only have to be right one time,” he reflected.
And he was. Shortly after, Cuban launched MicroSolutions, a software reseller company. With no outside funding and no time off (“I didn’t take a vacation for the next seven years,” he told The Playbook by Entrepreneur), Cuban hustled his way into profitability. By 1990, he sold MicroSolutions to CompuServe for $6 million. Nine years later, he made internet history by selling Broadcast.com to Yahoo for $6 billion.
From Sleeping on Floors to Owning the Dallas Mavericks
Cuban's early struggles were far from glamorous. He was fired from a computer store, lived with six roommates in a cramped apartment, and often slept on the floor. But instead of retreating, he went all in — and stayed all in.
“There is no balance,” Cuban once told Sports Illustrated. “If you want to crush the game, whatever game you’re in, there’s somebody working 24 hours a day to kick your a*s.”.
Sweat Equity Over Start-Up Capital
What if you’re starting with nothing today? Cuban says the answer lies not in bank accounts, but in sweat equity. If he had to build from scratch in 2025, he’d lean into artificial intelligence — and not by spending, but by learning.
“I’d be all about AI,” he said. “If I had access to a library and $0, I’d be in there till they kicked me out.” He suggests learning to prompt AI tools effectively, then offering services to small businesses to improve efficiency. In other words: find a skill, sharpen it for free, and sell it.
Despite his massive fortune (estimated at $6 billion, per Forbes), Cuban’s proudest achievement might just be the control he now exercises over his own time. At SXSW 2024, he shared a telling anecdote — after making his first million, he threw away his watch. “I didn’t want to respond to anyone else,” he said. “I wanted to own my time.”
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