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He sold his first company MicroSolutions, for $6 million. He did even better with his next company, Broadcast.com, which he sold to Yahoo for almost $6 billion.
Almost immediately after, Cuban sold all of his Yahoo stock, netting $2 billion in cash for himself. Weeks later, the market crashed.
Since then, Cuban has continued to work and invest. He owns the Dallas Mavericks and a cable channel. Plus he's all over the media - taking bites out of would-be entrepreneurs on ABC's pitch show "Shark Tank" and lighting up the conference circuit.
Cuban is known for saying what other people only think. Here are some of our favorite quotes.
Nicholas Carlson and Drake Baer contributed to an earlier version of this article.