Stroupe played shortstop at Cherryville High School where he was part of three state championship teams, and earned a scholarship to play at Appalachian State University for the Mountaineers baseball program from 1983 to 1986.
[1] After taking a teaching position after college graduation, Stroupe began to coach middle school baseball.
[4] From 1998 to 2002, Stroupe was the head coach at Lander University, where he started the baseball program.
In 2012, Stroupe received the prestigious FCA Jerry Kindall Character in Coaching Award (presented annually to the college or high school baseball coach in the United States who best exemplifies the Christian principles of Character, Integrity, Excellence, Teamwork and Service on and off the baseball field).
After retiring from coaching, Stroupe became a college professor, an ordained pastor, and a baseball color analyst for ESPN Plus.