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, was a member of their improv company from 2011 to 2014, and then continued his studies 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, Unexpected Results, Soap Scum, and the Winnipeg Improv Festival. Outside of improv, he works as a musician, composer, piano teacher, and accompanist for Sick + Twisted Theatre Company's drop-in choir. He completed a Bachelor of Music degree at Canadian Mennonite University in 2024 and has since been recovering by getting lots of sleep.