Simon was born in London and studied accountancy and finance at the City of London University. With his father Percy Kaye, he founded Jaguar Freight Services in both London and NY in 1993, and was the inspiration behind CyberTrax™, Jaguar's proprietary TMS. He moved permanently to the U.S. and established Jaguar's headquarters there in 2002. A fellow of the British International Freight Association, Simon is a dedicated fan and life-long season ticket holder of Tottenham Hotspur, who to their fans are "the greatest team the world has ever seen," a passion he feels about Jaguar.