Simon was born in Montreal, Quebec, Canada but his family moved to Saskatoon, Saskatchewan when he was a year old.He finished a Certificate in Business Administration at the University of Saskatchewan and worked a variety of jobs including: warehouse worker, arcade attendant, inventory clerk, rollerblading price-checker, Blockbuster Video, and Investors Group.It was during a tour of Universal Studios when Simon was bitten by the acting bug. His tour bus was outside the studio where Arnold Schwarzenegger was filming Kindergarten Cop (1990).Before his first speaking role, Simon has worked a variety of crew positions including set-security, production assistant, and extras wrangler. He has worked as an Extra (background performer), stand-in, and as a Special Skills Extra which involved firing a machine gun at Erika Eleniak in the movie, _Caught In The Headlights (2004)_.