Lots of people day-dream about what they'd do with a billion dollars.
Mark Cuban got to live it.
"Never in my wildest dreams did I think I'd be this rich, never," Cuban, who is currently worth $4.1 billion, recently told the Ringer. "And honestly, you couldn't spend it all."
Still, Cuban has made a dent. The very first things he bought were an impromptu party trip to Las Vegas, an island vacation and a giant mansion (of course).
The tech entrepreneur and owner of the NBA's Dallas Mavericks became a billionaire on paper at the age of 41 in 1999 when he and his co-founders sold Broadcast.com to Yahoo for $5.7 billion in stock. (The first thing he did after that was a naked "little billionaire dance," he's said.)
Then in early 2000, Cuban cashed in his Yahoo shares for a reported 10-figure payday. (It was good timing for Cuban, who sold his shares when the stock price was on its way to an all-time high that valued the company at $125 billion. Less than a year later the dot-com bubble burst and sank Yahoo's stock price to all-time lows.)
At the time, Cuban told The New York Times Magazine that he felt like he was "truly in a different league" the day he sold those shares and went from being a tech millionaire to a billionaire.
First he rounded up some drinking buddies to fly to Las Vegas, where everyone "just drank ourselves into a stupor," he told the Times.
Next, he took a vacation to the Bahamas with his then-girlfriend, Tiffany Stewart (they married in 2002 and now have three children together).
But Cuban's first truly major expenditure went toward a new home that would reflect the magnitude of his recent windfall.
At the end of 1999, Cuban spent $13 million on a 24,000-square-foot French chateau-style mansion in the affluent Preston Hollow neighborhood of Dallas, Texas. The house, where he and his family still live, has 10 bedrooms, a spa, pool, wet bars and tennis courts on a seven-acre estate.
"You open the door, and your house says a lot about you," Cuban told the Times in 2000, admitting that he enjoyed showing off the mansion to guests.
Cuban didn't stop there, though. He famously went online to buy a private jet for $40 million, also in 1999. His purchase of the Gulfstream V business jet still holds the title for the largest-ever single e-commerce transaction in the Guinness Book of World Records. (Cuban says he researched the plane on Gulfstream's website and then arranged the purchase with the company over e-mail before he'd even seen the plane in person.)
Buying a private jet "was my all-time goal," Cuban told Money in 2017, "because the asset I value the most is time, and that bought me time."
Weeks after buying the jet, though, Cuban moved on to a still bigger splurge — one that's significantly grown in value over the past two decades. In January 2000, Cuban paid $285 million for a majority stake in the Dallas Mavericks. Under his ownership, the team won an NBA championship in 2011 and is now valued at an estimated $2.3 billion, according to Forbes.
But when he bought the team, Cuban said it "never crossed my mind as an investment. I did it because I love basketball," he previously told CNBC Make It.
"I am just a huge Mavericks fan," Cuban said in a 2000 interview. "And I have just been blessed and put in a position where I can contribute."
Cuban reportedly started investing more money in the team immediately, paying to install DVD players and TVs in each players' stall in the team's locker room, upgraded the arena's Jumbotron and bought a new team plane — a $36 million Boeing 757.
In addition to the Mavericks, Cuban now also owns his own media production company, 2929 Entertainment, and he is a regular fixture on television, starring on ABC's "Shark Tank". Cuban's investment portfolio also includes a healthy stake in Amazon, that the billionaire claimed was worth roughly $1 billion in 2019.
With his multibillion-dollar fortune, Cuban, 61, recently told the Ringer he could always "buy more sports teams and blow it all there." In fact, he's expressed interest in buying multiple Major League Baseball teams, but so far has not found a deal.
But Cuban told the Times in 2000 that there was one "best" thing about being so rich: "being able to do what I damn well please."
Disclosure: CNBC owns the exclusive off-network cable rights to "Shark Tank."
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