Simon qualified as a Chartered Accountant with BDO Stoy Hayward (London) in 1980 before joining Landau Morley where he was promoted to partner later that year. From 1989 to 2002 Simon was Chairman and Chief Executive of Blacks Leisure Group plc. Simon is currently Deputy Chairman of Mishcon de Reya and The Leadership Trust, Chairman of a number of companies including Umberto Giannini, USA PRO, Espro Acoustiguide Group, First Sports Group plc and Maypole Group plc and also holds additional non-executive directorships.