Mark Cuban, the outspoken owner of the Dallas Mavericks, is worth an estimated $3.3 billion, according to Forbes. While the majority of this wealth can be attributed to two transactions he made during the dot-com era, he is a born entrepreneur and has been buying, trading, profiting and schmoozing his way to success from a young age. From his first business to today, here’s how Mark Cuban got rich.

The 1980s

During his undergraduate studies in Business Administration at Indiana University in Bloomington, Indiana, Mark Cuban scrounged together $15,000 to buy a bar. A professor at the university considered the move daring and confessed that he had never seen an undergraduate, or even an MBA student, have a business while still in school. Mark used his business savvy to turn the bar into the most successful student bar in town. After his university days were over, he continued to find opportunities to turn underdogs into winners.

Mark’s first business after university was MicroSolutions, a computer company which he sold after seven years to CompuServe in 1990 for a tidy sum of $6 million. Mark decided to use that money to retire and, for five years, lived the life of a party boy – he bought a lifetime pass on American Airlines and flew around the world in a quest to see as many countries as he could.

The 1990s

Five years later Mark’s retirement ended by a desire to listen to his former university’s basketball team’s games. Along with a partner he started AudioNet, which soon expanded to broadcast not only the Indiana Hoosiers games but hundreds of sports channels and radio programs, as well as product launches and fashion shows. The site, later renamed Broadcast.com, was one of the first internet radio sites in the world and when it had its IPO in 1998, the stock got caught up in the dot-com frenzy and soared from $18 to $62.75 in a single day.

Broadcast.com was later acquired by Yahoo! now Altaba (AABA) and Mark took in $1.7 billion in Yahoo! stock. He accurately foresaw the dot-com bubble burst and began to option and liquidate his Yahoo! stock as a means to protect his wealth. (For more, see: 6 Decisions That Cost Companies Millions.)

The 2000s

At the beginning of the millennium, some people were wondering how they had been so wrong about Y2K – Mark however, was closing the sale on his biggest purchase. For an astonishing $280 million, Mark became the majority owner of the Dallas Mavericks. The team was considered the worst in the league, but by 2011 Mark’s management had turned the team into NBA champions. The Mavericks are currently valued at $1.45 billion. The construction of a new $70 million practice facility is expected to result in a further bump to the team’s valuation in the coming years. 

In January 2018, Cuban confirmed that the Mavericks will accept Bitcoin and other cryptocurrencies as payment for tickets in the 2018-2019 season. Cuban was an outspoken critic of Bitcoin and famously called it a bubble in the summer of 2017, but went on to invest in the cryptocurrency later that same year. Cuban continues to expand his role in the crypto sphere, investing in tokens offered by Unikrn, an e-sports startup he funded, and backing the cryptocurrency fund 1confirmation.

When not watching his team from the sidelines, Mark is running 2929 Entertainment, a company which produces and distributes movies and TV shows. Here, his record is mixed as some of his movies have turned out to be duds. Others have made money, however. For example, the George Clooney-directed movie Good Night, And Good Luck had a production budget of $7 million and lifetime grosses of $54 million. This production company comes in handy if he ever needs content for his national theater chain Landmark Theaters or his satellite TV channel (the first one in HD) AXS TV. Mark is also known to still be investing large amounts of money in the stock market and, if his skills are as sharp as they were in the early part of the century, there’s no doubt that he’s making a lot of money. 

Having appeared in various shows and movies over the years, Mark is also a prolific media personality. The most famous of his shows is Shark Tank. But he has also appeared on Dancing with The Stars, Entourage, and Sharknado. The appearances serve a dual purpose in contributing to his net worth. They boost his profile in popular imagination, attracting important and smart people into his sphere of influence. And they bring in more business for him, whether it is in the form of promising startup investments or new opportunities. For example, Mark invested $1.75 million in obstacle course company Rugged Maniac during their Shark Tank appearance. An investment group purchased an 80% stake in the company in 2018. According to the Boston Globe, Cuban sold his stake for double the original amount of his investment in the company.   

The Bottom Line

Mark Cuban is a great example of someone who loves business and who is dedicated to rising up and becoming a self-made man. In addition to his media company and basketball team, he's also an investor in everything from toilet seats, various investing websites and sports technologies. Mark has also recently written a book and since 2012 has been a guest judge on the hit TV series “Shark Tank.” "Shark Tank" is an amazing opportunity for the guest judges to hear hundreds of previously vetted business proposals a year, and consequently have the chance to invest and manage them from the ground up. For a man who loves to grow businesses and get rich, Mark Cuban has found the perfect way to get incredibly wealthy.