Rupert grew up in Hampshire and the Sudan. He joined Country Life in 1994, after six years in the Household Cavalry, appearing at the Edinburgh Fringe as part of a comedy revue sometime in between. Rupert currently lives in West Sussex with his wife, their three children and a small menagerie, including a miniature poodle, Juno, several horses, 14 sheep, two saddleback pigs, two geese and five ducks.