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Simon is a writer, producer and executive producer within the film and television industry. He founded UK based drama production company Lookout Point in 2009, establishing a decade long relationship with the BBC group, which now owns 100% of the company. Some of the most notable company productions during his tenure include Andrew Davies' adaptations of War and Peace and Les Miserables for BBC One, five seasons of Ripper Street for the BBC and Amazon, Parade's End starring Benedict Cumberbatch for the BBC and HBO, Mike Bartlett's Press for BBC One and PBS, and Sally Wainwright's series Gentleman Jack for BBC One and HBO. He stepped down as Chairman and CEO of Lookout Point in early 2019 to launch The Media Investment Company with Helen Jackson and Jonathan Norman. The company will invest in building long term businesses around creative individuals and teams.