Born and raised on Long Island, Lenny graduated from Lynbrook High School in 1977. In 1980, he earned an A.A. in Liberal Arts from Nassau Community College. He moved to Southern California later that year and, in 1983, graduated from Cal. State Fullerton with a B.A. in American Studies.

With degree in hand, Lenny moved to Los Angeles and began a campaign to become a television writer. He worked many odd jobs during that time, including shoe salesman, Zamboni driver, bartender/cater waiter, and his favorite, substitute teacher.

Having no luck peddling his t.v. scripts, he returned to college in the late eighties to obtain a teaching credential. After landing a part time teaching job in 1988, he was soon offered a full time position... under the condition he remain in school and complete the credential program.