Toby grew up on his parents' Hill Jock Farm in Chelmsford, Massachusetts.  As a youth he was a member of both the local 4-H and the Concord Pony Club.  While in Pony Club, he was first introduced to the competitive sport of eventing.  After attending the Michigan School of Horseshoeing, he continued to event his thoroughbred gelding, Murphy's Law, at the preliminary level.  In 1984, Toby took an interest in the Western disciplines and started showing at American Quarter Horse Shows.  The following year he started reining and in his first year as a member of the Northeast Reining Horse Association, he captured the Premier Championship.  Since then, he has turned pro and captured numerous NERHA and MQHA Championships, along with two Reserve Congress titles.  Toby is a popular National Reining Horse Association judge, and promotes Quarter Horses bred and raised at Twin Pine Farm and select client horses.