Born into a wine making family, Rolland grew up on the family's estate Château Le Bon Pasteur in Pomerol. After high school, Rolland enrolled at Tour Blanche Viticultural and Oenology school in Bordeaux with his father's encouragement. Excelling in his studies, he was one of five student chosen by director Jean-Pierre Navarre to evaluate the program's quality against that of the prestigious Bordeaux Oenology Institute. Rolland later enrolled in the institute, where he met his wife and fellow oenologist, Dany Rolland, and graduated as part of the class of 1972.