Rupert is an economist known extensively for his work in real estate, investment analysis, urban renewal and economic development. In 1985 he founded the Investment Property Databank (IPD), which is the major provider of property information, indexes, and benchmarks round the world. Prior to this he worked in the areas of urban renewal and local economic development. A keen gardener and supporter of the arts, commissioning early works from Andy Goldsworthy and others, he was founding Chair of Common Ground and a Trustee of Winchester Poetry Festival. Rupert was a long-standing trustee of Common Ground and has organised arts exhibitions and festivals in his local area.

He has been a YSP Trustee since 2013 and is a member of the Finance & General Purposes committee.