Simon graduated from Highland High School in 1994. He attended Southwest Missouri State University where he had a full soccer scholarship and then transferred to North Carolina State University where he graduated Magna Cum Laude with a degree in Chemistry. In Highland, Simon was in on the ground floor of the Bulldog soccer program in 1986, but also played baseball and basketball. He was named an all-conference player at Southwest Missouri State, but chose to transfer to North Carolina state, the #1 ranked soccer team in the country. Simon started in 33 of 37 games and help lead the Wolfpack to the NCAA semi-finals. Following graduation, Simon played professionally for several years in France, England, Sweden and the US. He is now a credentialed soccer coach with the US Soccer Federation and has a Premier Diploma from the National Soccer Coaches Association of America.