Simon began as a Crosseyed Rascal in 2022, but he has been a long-time friend and guest performer with the troupe reaching all the way back to 2018. He started performing improv in 2010 as a student at Manitoba Theatre for Young People and as a member of their improv company from 2011 to 2014, then continued at Prairie Theatre Exchange. If needed, Simon will occasionally play an instrument during a show and has played for Outside Joke, The DnD Improv Show, and Unexpected Results. Outside of improv, he works as a musician, composer, and choir director. Simon recently graduated from Canadian Mennonite University with a Bachelor of Music. Since then, he has been recovering by getting lots of sleep.