Cutler was raised in Philadelphia, Pennsylvania. He began his early career hosting teenage dances in Pennsylvania starting in 1961.[1] He eventually transitioned into radio broadcasting as "DJ Ron Diamond", becoming one of the first disc jockeys to play both contemporary music and oldies on FM radio.[1] After moving to San Jose, California, Cutler and a partner, Mel Gollub, took over KUFX in 1970, renaming it to KOME in 1971.[2]
A veteran radio producer, Cutler worked extensively with a number of entertainment figures including Rick Dees, Tom Joyner, and Cousin Brucie throughout the 1980s and 1990s.[3] In the early 1990s, he eventually opened his own radio station, KTUN-AM, which focused on playing movie and show tunes.[4] Cutler founded and ran Cutler Comedy Networks, a radio prep service.[5] It was acquired by Premiere Radio Networks, itself a subsidiary of iHeartMedia.[1][6] With his son Max Cutler, Cutler started Parcast, a podcasting network and distribution platform, in 2016.[5] The network has launched over 18 podcasts.[5]