Simon started his career in the Valuation Office based in Camden central London. After qualifying for Chartered status he was promoted firstly to Valuer then to Valuer Main Grade. He dealt with Capital Gains Tax and other tax valuations as well as rating and appeared before the Lands Tribunal in 3 separate cases and prepared another 7 cases before being offered the position of office manager for the Covent Garden office of local firm Sweby Cowan. There he rose to associate then Partner dealing with a wide range of valuations and agency work in the vibrant and then rapidly developing Covent Garden which was in the process of turning itself into a major shopping destination. Later he was responsible for the Valuation team and based at the main West End office where he set up a specialist Licensed and Leisure property division for their practice and was involved in a number of high profile hotel acquisitions and valuations in particular before taking on the role of local partner managing the Wembley office, which dealt with large industrial units in particular.

He left Sweby Cowan and set up his own practice initially based in Hampstead north London and later in Bath and then was recruited to set up a new South West regional commercial department for Black Horse Agencies (then part of Lloyds Bank) based in north Bristol. The department expanded and began to undertake commercial valuation work as well as rating and he moved to set up a new commercial regional base in Southampton where he became involved in a number of joint projects with Aitchison Raffety.

In due course he took the natural step of accepting a position with Aitchison Raffety and has been undertaking Rating and Valuation work, in particular in the Licensed property sector, for them since and is now a local Director.