 Stealey graduated from the United States Air Force Academy in 1970 and was, at the time he co-founded Microprose, a Major in the USAF Reserve and instructor for the Pennsylvania Air National Guard, flying A-37 attack aircraft.He retired from the military with the rank of Lt Col.

Stealey owned the Baltimore Spirit of the National Professional Soccer League from the franchise's inception in 1992 until he sold it to Edwin F. Hale, Sr. in 1998.