Leo grew up and attended schools in Glendale, California before being accepted to the University of California, Santa Cruz, where he earned his degree in History. Following his graduation from UC Santa Cruz, he chose San Francisco State University to earn his California Teaching Credential.
He was hired at San Leandro high school in 1999 and commuted from Vallejo every day for the past 13 years. Over his career at San Leandro High School, Leo has taught US History, Modern World History, Government, Economics and most recently began teaching Psychology. Leo is also the Social Science Department Chair and most recently served as the Chair of the School committee for the Western Association of Schools and Colleges accreditation. Leo also spearheads the school wide Reading Appreciation Program (RAP).