Intrigued by the opportunities in the emerging intersection of information and technology, Spain then joined the Extel Corporation, a telex manufacturer, as an associate counsel.
[citation needed] During this period, Spain provided some of the initial capital for the creation of Bookstop, a company founded by his friend Gary Hoover.
The wide exposure provided by America Online and the Company website, led to Hoover's rapid growth, with a public stock offering in 1999.
In 2013, he became a Director at Owler,[5] an innovator in company-related content started by Jigsaw founder Jim Fowler, where he continues to serve on the Board.
[10] Spain's interest in creating First Stop Health arose from his own unsatisfactory experience with the healthcare system, when a member of his family experienced a serious illness.
[10] His father, James W. Spain, was a career foreign service officer and a U.S. ambassador to Tanzania, Turkey, and Sri Lanka.