Councillor Hesse-Phillipson was born in London and shortly after moved out to Rickmansworth. At the age of nine he moved to Wootton-under-Edge in Gloucester. He was educated near Hastings and in Cheltenham and joined the Royal Artillary after school.

Councillor Hesse-Phillipson spent twelve years in the forces which included a tour of Northern Ireland and the Falkland Islands during the troubles. In 1987 he left the forces and moved to Gainsborough where he and his family have lived since and had a delivery job for twelve years.

Councillor Hesse-Phillipson has four children, three who live in Gainsborough at present and thirteen grandchildren.