Osteen first wrestled in 1980 while serving in the United States Air Force, competing in freestyle and Greco-Roman wrestling in open tournaments until 1989.  He was a middle school coach for eight seasons at Flat Rock Middle School, Rugby Junior High, Edneyville, and Apple Valley Middle. During that period his teams won five conference championships.  Osteen also coached high school teams for five seasons at Edneyville, North Henderson, and East Henderson.  At North Henderson, his team was the dual team runner-up and the state tournament champions in 1994.  Osteen also coached at Gardner-Webb University and coached a club team at Wofford.  In 1989, Osteen founded the Strong and Courageous wrestling club in Hendersonville. For the past 28 years, Osteen’s club has not only developed champion wrestlers, but also served as a sports ministry.  As Osteen has directed Strong and Courageous, he has been heavily involved with both NCUSA Wrestling and USA Wrestling. Coach Osteen has traveled internationally, attended the Olympic Games, and served as the Greco-Roman delegate to Puerto Rico for nine years. Osteen was named USA Kids-Cadet Person of the Year in 1995 and the Fila Jr / University Person of the Year in 2001. Osteen has also been designated as the Southeast Regional Person-of-the Year. To date, Osteen has coached multiple national champions and over 50 All-Americans at various national competitions. As of 2016, Osteen had also coached an impressive 41 All-Americans at the Asics / Vaughan Cadet / Junior Nationals held annually in Fargo, North Dakota.