He began drawing cartoons on washroom walls as a kid. After being expelled from his first (and last) art class at the age of 15, he moved with his parents to England, then to Canada. While there, he worked at various jobs, from loading grain ships in Thunder Bay, Ontario, to surveying on the West Coast. Illustrating his mother Joan Raeside's children's books got him his start in the art business. Raeside began drawing editorial cartoons for the Times Colonist in Victoria, British Columbia in 1979.