A graduate of Pepperdine University, Housley played on the 1992 National Champion College World Series baseball team and spent two summers playing for Harwich in the Cape Cod League. He was also a Junior Olympic All-American baseball player as a pitcher and hitter. He received a double bachelor degree in political science and telecommunications from Pepperdine University. He was a two-time media fellow at the Hoover Institution at Stanford University and received his MA in international relations from the University of Arizona. Prior to his career in television, Housley played professional baseball and was drafted by the Montreal Expos and played for both the Milwaukee Brewers and the Detroit Tigers minor league organizations, pitching in 97 games.