Raised in a small town outside of Toronto, Simpson has painted since the age of 13, and found it an outlet for, “dealing with a typical, god-fearing Pentecostal family in the ‘burbs.” Simpson studied at OCAD University (formerly, Ontario College for Art and Design) for a short time, though he never actually enrolled in a painting class. After being awarded the highest prize in painting scholarships he was asked to leave for “failing to achieve the standard 64% grade percentage.”