Wyly begins by recounting his childhood, and education prior to going to work for IBM’s Service Bureau Corporation, and then joining Honeywell as an area sales manager. He discusses how he left Honeywell to form University Computer Corporation (UCC), a firm that sold computer time, but transitioned into a software services business. Wyly explains his growing focus on computing and telecommunications, his formation of Datran, and his unsuccessful attempt to acquire Western Union. Much of the interview focuses on ongoing developments at UCC, the eventual sale of this firm to Computer Associates, his formation of Sterling Software, its acquisition of Informatics, the sale of Sterling, and his ideas on the future of information technology. Throughout Wyly’s discussion of UCC and Sterling, he elucidates upon his leadership philosophy, and the strategic, technical, operational, and financial management of these firms. This oral history was sponsored by the Software History Center in conjunction with the Center's ADAPSO reunion (3 May 2002).