Simon grew up in the town of Milton, Ontario. During high school, he competed in alpine ski racing and upon graduating he transitioned into a coaching role in order to pursue a degree in Kinesiology with a minor in Psychology at McMaster University in Hamilton.
During his first year in law school at The University of Western Ontario, Simon visited Vancouver for the first time. Shortly after that, he moved to Vancouver to complete his legal education at the University of British Columbia, graduating in 2009.
As a law student, Simon founded the Western Epicurean Club and was an active member of the UWO Social Committee. Simon also worked as a research assistant in the area of Aboriginal law.
Since his second year of law school, Simon has worked exclusively in the field of plaintiff personal injury law representing people who have been injured by others. Simon has successfully represented people who suffer from soft tissue injuries, orthopaedic injuries, spinal cord injuries, and psychological trauma in both the Provincial and Supreme Courts of British Columbia in cases that involve complex liability and causation issues.
Outside of work, Simon volunteers his time with Big Brothers of Greater Vancouver. He can also be found making fresh tracks in Whistler or fishing the rivers and lakes that BC has to offer.