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Cuban's company, MicroSolutions, began as a system integrator and software reseller. One of the company's clients was Perot Systems. In 1990, he sold MicroSolutions to CompuServe (a subsidiary of H&R Block) for $6 million. Cuban furthered his knowledge of entrepreneurial leadership and investing with his second company, Broadcast.com, which helped launch the first live-streamed Victoria's Secret Fashion Show. (Getty)