Simon was born in Plumstead in 1977, and still lives in the Shooters Hill area of Plumstead, with his wife and two daughters.

After leaving college at 18 Simon began working for London Underground in May 1996, where he became a Duty Manager in August 1999, at the age of 22.

Outside of politics Simon is a Charlton Athletic season ticket holder, a Kent Cricket Club supporter, a  member of CAMRA, a motorbiker, a bass guitarist, and was also a football referee for 14 years with the London FA. He has also raised funds for a number of charities by running the London Marathon four times. Simon is also a dedicated Scout Leader in Woolwich, having joined the Scouting movement as a Cub Scout at the age of 8. In addition to being a Scout Leader he also holds the District appointment of Training Manager, for the Woolwich Scout District, responsible for the  training of all adult volunteers.

Through his work as a Scout Leader, and as a manager, Simon became a full Member of the Institute of Leadership & Management (MInstLM) in 2006, and was awarded the Licentiateship Management Award from the City & Guilds Institute (LCGI) the same year.

In the world of blogging Simon began to write the blog ”The Last Boy Scout” in 2006, where he wrote articles mainly on national issues. After a failed venture of setting up a local posts only blog “The Last Boy Scout’s Back Yard” he took the decision in February 2009 to change the focus of the blog, and create a new one in his name, to include more local stories.

Simon joined the Conservative party in 2005 and stood as a candidate in the Greenwich Council local elections in 2006 – for Plumstead ward, and  in 2010 – for Shooters Hill ward.