Simon studied classical improvisation with Dr David Dolan at the Guildhall School of Music and Drama. Shortly after graduation, David invited Simon to work with him teaching for the Centre for Classical Improvisation and Creative Performance at Guildhall, where he has worked since 2009, coaching hundreds of undergraduate and postgraduate students across all instruments. The course offers a unique bridge between theory and performance for classical musicians, fusing deep awareness of harmonic direction with real time musical flow. The focus on improvising in ensembles trains active listening skills, vital for chamber or orchestral musicians.
Together with fellow Guildhall graduates trombonist Miguel Tantos and violist Drew Balch, he formed the Prima Volta Ensemble. This ground breaking ensemble performed entire concerts where every note is improvised, taking all their themes, keys, forms and abstract ideas from suggestions from the audience. Typical concerts would include pieces in a range of styles, from renaissance or baroque pastiches right up to contemporary languages. The ensemble frequently led workshops in improvisation, including a course at Trinity Laban, and a number of residencies with Aldeburgh Young Musicians.