Brewster has been musically inclined since his early childhood in Homer, Alaska. At the age of one, his mother, Cheryl, noticed how well he could keep rhythm on a drum set his grandfather had given him. At the age of five, his mother introduced him to the mandolin. Quickly mastering the instrument, he began playing for cruise ship tourists alongside his mother in Homer, Alaska. After receiving a call from Steve Perry inviting him to audition as lead guitarist for his next solo project