After graduating from film-school in 1995, Simon produced acclaimed music videos for indie record labels such as Mute, Deceptive and Ché. In 1996, he was signed for representation by Propaganda Films where he directed music videos and concert films for MTV, Sony, Warners and other labels.

Between 2000 and 2005, Simon filmed and edited interviews and performances for music website playlouder.com, including award-winning coverage of the Glastonbury Festival. In 2006, he set up production company Amarcord Media through which he has continued to produce, film and edit media for television, film festivals and the internet for organisations and companies including The British Museum, The British Film Institute, The Arts Council, The Royal Institute of British Architects and The National Gallery.

In 2007, Simon was commissioned to produce several films for Emmy-award winning television station, Current TV. The following year he was commissioned by art agency All Visual Arts to direct a feature length documentary, Ascent into the Maelstrom, about the work of artist Paul Fryer. It played at festivals and in galleries around the world and won the award for Best Arts Film at the 2010 Portobello Film Festival.

In 2008, he set up newwavefilm.com, the internet's leading resource on the French New Wave and other international New Wave film movements. The website is used as a resource for educators and has appeared in numerous text books and as material for university courses.

From 2010 - 2019, Simon worked as an in-house filmmaker at the British Museum where he produced, directed, filmed and edited films including: documents of popular exhibitions, video press releases, filmic records of lectures, live events, and projects such as the construction of the World Conservation and Exhibitions Centre, promos for the Membership Department and schools programs, and film documenting public screenings including the British Film Institute's restored version of Alfred Hitchcock's silent masterpiece Blackmail.

Amarcord Media is currently developing a number of independent projects for web and television.