In the 1970s, Grimassi recorded a garage rock song with Ritchie Brubaiter, called "Brat". After studying psychology in college, he worked for a few years for San Diego County Mental Health Services inside a secure psychiatric facility. He shifted to a center for abused children, then worked as a counselor for drug and alcohol abuse patients. The stress of these jobs moved him to study cosmetology and become a hair stylist for many years. After that he served as a financial aid counselor, then in the mid-1990s his book publishing income allowed a full-time writing career.