 Over forty years Sherwood expanded Sea Containers from a supplier of leased cargo containers, into various shipping companies, as well as expanding the company into luxury hotels and railway trains, including the Venice-Simplon Orient Express and Great North Eastern Railway that operated the InterCity East Coast franchise.Although valued with a net worth of £60million in the 2004 Sunday Times Rich List, as Sea Containers hit financial troubles, he resigned as Co-Chief Executive Officer from each of his companies in 2006..He continued as a Director of Orient Express Hotels Ltd until retiring on 9 June 2011.