Harold was born in Frankfurt, Germany to an American military family. His childhood was spent in places around the U.S. including El Paso, Texas; Chaparral, New Mexico; White Bear Lake, Minnesota; and Anchorage, Alaska. He also spent a significant period of his early life in Europe, living in Kaiserslautern, Germany and traveling with his family extensively.
When Harold was 11 his family saw a production of Shakespeare's Taming of the Shrew in London's Regent's Park. He was enthralled by the non-traditional production, and decided to try his hand at acting. School and Community Theatre productions followed, as well as individual lessons and classes. By the time he started high school in Anchorage, Alaska Harold had already appeared onstage and worked backstage in several productions. Harold was fortunate to attend East Anchorage High School, which was noted for its commitment to theatrical excellence.
He enrolled at the University of Alaska at Anchorage in 1989 and quickly found a place in the college's Department of Theatre and Dance. While at UAA he began his training in stage combat, and became a certified member of the Society of American Fight Directors. After three years at UAA Harold transferred to Western Washington University. He met his future wife Trish Egan while performing in the college's summer stock program. After a year's long-distance courtship, Trish convinced Harold to join her in Portland, OR and finish his academic career at the University of Portland, her alma mater. After college Harold worked in a variety of Portland-area theaters.