He spent much of his free time with his father, Tom Holliday, and brother, Josh, at the Oklahoma State University (OSU) baseball field and training complex, where his father was a coach. There, the Holliday boys learned about the fundamentals of the sport, voluntarily trained and practiced, and watched future major leaguers such as Robin Ventura play and develop. In addition, he played American Legion Baseball during the summer. In spite of the extensive time spent around the sport of baseball, Tom Holliday abstained from attempting to influence his sons on which sport or sports to concentrate.