In 1982, Cuban moved to Dallas, Texas. Cuban first found work as a bartender, then as a salesperson for Your Business Software, one of the first PC software retailers in Dallas. He was terminated less than a year later, after meeting with a client to procure new business instead of opening the store.
Cuban started a company, MicroSolutions, with support from his previous customers from Your Business Software. MicroSolutions was initially a system integrator and software reseller. The company was an early proponent of technologies such as Carbon Copy, Lotus Notes, and CompuServe. One of the company's largest clients was Perot Systems. In 1990, Cuban sold MicroSolutions to CompuServe—then a subsidiary of H&R Block—for $6 million. He retained approximately $2 million after taxes on the deal.
In 1995, Cuban and fellow Indiana University alumnus Todd Wagner started Audionet, combining their mutual interest in college basketball and webcasting. With a single server and an ISDN line, Audionet became Broadcast.com in 1998. By 1999, Broadcast.com had grown to 330 employees and $13.5 million in revenue for the second quarter. In 1999, during the dot com boom, Broadcast.com was acquired by Yahoo! for $5.9 billion in Yahoo! stock