Having left King Edward VI school aged 16, Simon started at The Dartington Trust owned Staverton Joinery in July 1997. He began his apprenticeship in French Polishing there in 1998.

During the three years of his apprenticeship he attended South Devon College to gain Craft and Advanced Craft in painting and decorating, passing with triple distinctions. He completed his apprenticeship in 1991.

During the summer months of 1991 he worked for South Hams District Council as a gardener at Follaton House Gardens. In September he attended the first full-time traditional signwriting course at South Devon College and went on to a second year to achieve another set of triple distinctions.