Guest played as a ruckman in the 1963 U19s Carlton premiership side.

Early in 1963 he was picked to represent the club at an interstate carnival in South Australia.

Since then Bob met his future wife, Sandy while both teaching at Shepparton South Tech. After football and starting a family Bob completed a Master of Education at the University of Calgary, Alberta, Canada in 1988 and earned his PhD at the University of Calgary in 1992. Upon retirement from education, he worked for 10 years as an Electoral Official for the Victorian Electoral Commission.

Robert is cousin of Carlton Thirds player from the 1930s, Jack Guest.