Taylor's first boarding school experience came at The George School, and then Millbrook School, where his father worked in the admissions office. His family eventually made their way to Williamstown, Mass., where he grew up and attended the public high school in the area. In high school he played four years of varsity soccer, captaining the team during his senior year and earning league MVP honors. He also was captain of the tennis team during his junior year. Outside of school, he had been learning the game of squash since sixth grade and continued to play the sport throughout high school, having a successful career on the junior circuit.
Taylor attended Williams College where he majored in political science and played on the varsity squash team. He spent his junior year as a Junior Advisor, a prestigious role at Williams in which a pair of juniors live with freshmen and play an important role in their first year. During his senior year, he captained the squash team and was selected Second Team All-NESCAC.
At St. Andrew's, Taylor works in Admission and coaches soccer, squash, and tennis.