Miles was educated at Harrow and Christ Church, Oxford. He entered the City in 1982 working for the stockbrokers, Rowe and Pitman. In 1985 he moved to the US investment bank Donaldson, Lufkin and Jenrette; he stayed there for 15 years working on US equity desk. Miles then moved to Norfolk and now works as a wealth management consultant and angel investor as well as looking after the family farming company.
Previously a governor of Beeston Hall Prep School and Rugby School, he also served as a trustee of the medical emergency relief charity Merlin for 3 years. As well as Ovalhouse, he is currently involved with Pilotlight, which brings the experience and skills of business people to the voluntary sector.