He is part of the seventh generation of the Weatherby family, known for its involvement in horseracing.
Roger attended Eton College and later trained at The Royal Military Academy Sandhurst.
He served in The 15th/19th The King's Royal Hussars from 1982 to 1985, including postings in Germany and Cyprus.
After leaving the Army, Weatherby worked as an institutional equity salesman at Cazenove & Co in London, Sydney, and New York.
He has participated in several high-profile fundraising efforts, including an expedition to the South Pole and multiple marathons.