Before ultimately choosing football as a career, Simon enjoyed great success as a basketball player at a young age. He also took up baseball and track, but became attracted to football after watching Walter Payton. Envisioning a career in professional football, he accepted a scholarship offer from the University of Maryland. During his spare time, Simon has said that he listens to B.B. King, watches SportsCentre, and plays pool. Simon also coaches his son's minor football team. Simon lives in Langley, British Columbia, during the CFL season with his two children Jaden and Jordan.