Cuban has been a businessman since the beginning. When he was a senior at Indiana University, he and a friend bought a bar called Motley’s in downtown Bloomington. It was eventually shut down after they named an underage girl the winner of a wet t-shirt contest held on the premises.
Cuban sold his first company, a consulting firm called MicroSolutions, to CompuServe in 1990. Next, he decided to pay $125,000 for an American Airlines lifetime pass, which let him fly first-class anywhere in the world. “I got as drunk as I could with as many people as I could meet,” he told the Financial Times.
Source: FT, Esquire
As of 1:16 pm on January 8, 1999, Cuban was a billionaire. He described the moment during a podcast with James Altucher: “I was sitting in front of a computer, naked, hitting the refresh because we were close — waiting until my net worth hit that billion.”
Frederick M. Brown/Getty Images
Source: Business Inside
In addition to 10 bedrooms and 13 bathrooms, the home has a wine cellar, eight-car garage, and a three-story pavilion overlooking a swimming pool.
Cuban took People magazine inside his home office in 2013. “The biggest change in my life since I moved in here 14 years ago is of course, the kids,” he said. “I didn’t even go up to the second floor of this place for years until we had kids.”
Cuban met his future wife, Tiffany Stewart, at the gym in the late ’90s. They married in a super-secret ceremony in Barbados in 2002.
Kevin Winter / Getty Images
Together they have two daughters and a son.
Jonathan Ferrey/Getty Images
One of his daughters, Alexis, got to attend the 2014 American Music Awards with her dad.
Jason Merritt/Getty Images
Cuban’s biggest splurge by far has been his January 2000 purchase of the Dallas Mavericks. He paid $285 million to take over majority ownership from Ross Perot, Jr.
Cuban has also splurged on several private jets. When he bought a Gulfstream V online in 1999, the Guinness Book of World Records named the $40 million purchase the largest e-commerce buy ever.
He also owns a Boeing 767 that he makes available for luxury charter. Cuban told Business Jet Traveler, “It’s part of my life that I can’t be without. It means I have more hours in my day to spend with friends and family. It means I can get more work done.”
Source: Business Jet Traveler
His third plane, a Boeing 757, has been outfitted with a weight room and oversized seats for use by the Mavericks players. “When you are on the road as much as an NBA team has to be, the ability to be comfortable, get rest and have enough room for basic treatment of physical problems gives us a competitive advantage,” he told the Dallas Morning News.
Source: Dallas Morning News
Cuban has reportedly owned a home in Manhattan Beach, California for years, and he’s often been spotted at local bars there.
Cuban also owns a few properties in New York City, including nearly the entire 45th floor of the Trump International Hotel and Towers at 1 Central Park West. According to Variety, he has several condos that total approximately 5,778 square feet.
Beyond My Ken / Wikimedia Commons
He also owned a one-bedroom apartment at 257 Central Park West, which he listed for $600,000 in 2013.
Tdaileader / Wikimedia Commons
Source: The Real Deal
When in Dallas, Cuban gets around town in a black Lexus SC430 with the license plate “MFFL” (or Mavericks Fan For Life).
Cuban is known for his hard-partying lifestyle and throws an annual bash during Super Bowl weekend. Kanye West and Rihanna were among the performers at this year’s celebration.
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After the Mavericks won their first championship in 2011, Cuban famously racked up a $110,000 bar tab while partying at Miami’s Club Liv with Dirk Nowitzki, Jason Terry, Brian Cardinal and Shawn Marion.
Source: Page Six
He later took a trip to the White House to celebrate the championship with President Obama himself.
Cuban often returns to his alma mater to offer his business advice and conduct Q&A’s with students. He also comes back to party at Bloomington’s local bars.
In 2012, video surfaced of Cuban dancing to “Gangnam Style” at Kilroy’s, a sports bar in Bloomington.
In 2014, he got to wave the green flag that marks the start of the Indy 500.
Michael Hickey/Getty Images
Source: Indy Star
Most recently, he created Cyber Dust, an app that lets you send messages that disappear after a certain amount of time.
Check out Cyber Dust »
Known for his loud and energetic personality, you can always catch Cuban yelling courtside during Mavericks games.