After years of odd jobs as farm hand, ships' mate and plumber, Simon became a Youth and Community worker in a poor area of London for 14 years. He also worked on campaigns around AIDS and prostitution in the 1980s, and on multi-national corporations such as McDonalds, Shell and RioTinto. Simon trained as a documentary filmmaker at the National Film and Television School, and graduated in 2004, winning the Royal Television Society award for best European student documentary. He began his career with several "Three Minute Wonders" for Channel Four as well as charity videos in India. In 2006 he completed a fiction feature script, commissioned by Film Four and also shot and directed a one hour documentary "Every Good Marriage Begins With Tears" which screened on BBC Storyville and was bought by TV channels around the globe, winning a clutch of awards at film festivals. His 2009 documentary "Cowboys in India" has screened on Channel 4 True Stories strand, and his co-production "Mario and Nini" on Sky Channel.