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Stealey is a graduate United States Air Force Academy in Aeronautical Engineering (1970) and of the Wharton School of the University of Pennsylvania with a Masters of Business Administration. He also received a four year ROTC scholarship and attended Pennsylvania Military College for one year before attending the USAF Academy. He 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.
An avid aviator, Stealey and piloted a North American T-28 Trojan for over 15 years including leading the T-28 formations at the Oshkosh Air Shows every July on a number of years. In 2005, Stealey attended Wake Technical Community College Digital Game Xpo as a guest speaker.
In 2012 iEntertainment merged with Great Outdoors LLC, a private company and he is now the Chairman of the Board of the combined companies.
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