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.

View image on Twitter

View image on Twitter

Follow

Mark Cuban

 

@mcuban

This was an ad for the bar we started at IU. Yes we had nerf basketball and you didn’t

  •  
  •  

    439439 Retweets

  •  

    1,1281,128 likes

 

 

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.

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.

Courtesy of Mark Cuban

Source: FT, Esquire

 

But Cuban really made it big when Yahoo bought Broadcast.com, a live audio and video streaming site Cuban founded with friend Todd Wagner. The deal, finalized in 1999, was valued at nearly $6 billion.

But Cuban really made it big when Yahoo bought Broadcast.com, a live audio and video streaming site Cuban founded with friend Todd Wagner. The deal, finalized in 1999, was valued at nearly $6 billion.

Reuters

Source: 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.”

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

 

One of the first things he did was buy a mansion worthy of the billionaire title: a 24,000-square-foot home in the Preston Hollow neighborhood of Dallas. Purchased for $15 million in 2000, the house is now worth about $17.3 million, according to Dallas public assessor records.

One of the first things he did was buy a mansion worthy of the billionaire title: a 24,000-square-foot home in the Preston Hollow neighborhood of Dallas. Purchased for $15 million in 2000, the house is now worth about $17.3 million, according to Dallas public assessor records.

Bing Maps

Source: Business Insider

 

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.

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.

Bing Maps

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 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."

Screenshot, People

 Source: People

 

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.

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

Source: ESPN

 

Together they have two daughters and a son.

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.

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'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.

Associated Press

Source: Star-Telegram

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.

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.

Greg Bishop, Flickr

 

 

 

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.”

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."

Flickr / smartjunco

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.

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.

Flickr, pdx_rollingthunder

Source: Dallas Morning News

His 288-foot yacht, “Fountainhead,” was built in 2012. A sister ship to Larry Ellison’s “Musashi,” the two boats look nearly the same from the outside, though Cuban reportedly went for a more antique-inspired interior.

His 288-foot yacht, "Fountainhead," was built in 2012. A sister ship to Larry Ellison's "Musashi," the two boats look nearly the same from the outside, though Cuban reportedly went for a more antique-inspired interior.

Michael Hickey/Getty Images, stephrog/Flickr

Source: Forbes, Boat International

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.

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

Source: Variety

He also owned a one-bedroom apartment at 257 Central Park West, which he listed for $600,000 in 2013.

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).

When in Dallas, Cuban gets around town in a black Lexus SC430 with the license plate "MFFL" (or Mavericks Fan For Life).

order_242 / Flickr

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.

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.

Christopher Polk/Getty Images for DirecTV

 

 

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.

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.

Danny Nunes/Twitter

Source: Page Six

He later took a trip to the White House to celebrate the championship with President Obama himself.

He later took a trip to the White House to celebrate the championship with President Obama himself.

Getty Images

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.

In 2014, he got to wave the green flag that marks the start of the Indy 500.

Michael Hickey/Getty Images

Source: Indy Star

These days, Cuban appears as one of the shark investors on ABC’s “Shark Tank.” He also invests in a number of companies outside of the show, including Clarity, uBeam, Slideshare, and Inside.com.

These days, Cuban appears as one of the shark investors on ABC's "Shark Tank." He also invests in a number of companies outside of the show, including Clarity, uBeam, Slideshare, and Inside.com.

ABC/Michael Desmond

Most recently, he created Cyber Dust, an app that lets you send messages that disappear after a certain amount of time.

Most recently, he created Cyber Dust, an app that lets you send messages that disappear after a certain amount of time.

iTunes

Check out Cyber Dust »

Known for his loud and energetic personality, you can always catch Cuban yelling courtside during Mavericks games.

Known for his loud and energetic personality, you can always catch Cuban yelling courtside during Mavericks games.

Mpu Dinani/Getty