Olivia started riding at the age of 3 with formal lessons at 6 under the tutelage of Jerre Frankhouser. She always maintained a strong bond with ponies spending hours watching the pony breeding and pony hunters at the Devon Horse Show. In 1985 she won the Small Pony Hunter Stake class with her first small pony Short Stop and through the years picked up numerous wins in the pony ring.

In 2003, Olivia founded Double G Stables, which specializes in producing national champion hunter ponies. She starts young ponies from the ground up, rehabilitates difficult ponies and trains green or inexperienced ponies for the hunter ring. Utilizing the methods of Clinton Anderson, she carefully starts her ponies to provide a strong foundation for their career in the hunter ring. Olivia's ponies have gone on win championships at top competitions including the USEF Pony Finals, USEF Pony Medal Finals, Vermont Summer Festival, Horse Shows by the Bay (Michigan), Showplace Spectacular (Chicago) HITS at Saugerties and Winter Equestrian Festival in Wellington, FL.