Cuban began his career at the age of 12 in his native Pittsburgh, selling garbage bags to finance a pair of basketball shoes. Later, he co-founded Broadcast.com with Todd Wagner and used proceeds from its sale– it was acquired by Yahoo for $5.7 billion in stock in 1999 – to acquire NBA’s Dallas Mavericks and the arthouse movie chain Landmark Theatres and co-found the cable channel HDNet (now AXS TV).

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A professed admirer of objectivist author Ayn Rand (“The Fountainhead”), Cuban has invested in a myriad of startups over the years, from investigative web site Sharesleuth.com to high-tech toilet maker Brondell Inc. He’s also put more than $19 million into companies in his four years on the ABC reality series “Shark Tank” and appeared as a contestant on “Dancing with the Stars.”

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In 2016, Cuban made more headlines with his charitable activities and political comments than he did with his business dealings. Following the Orlando nightclub shooting in June, he donated $1 million to the Dallas Police Department to help it protect the city’s LGBT community. The following month, Cuban – an independent with Libertarian leanings – endorsed Hillary Clinton for president.