Gregg worked as a paper boy to afford a Silvertone guitar, which he purchased at a Sears when he saved up enough funds. Like his brother, he was left-handed, but played the guitar right-handed. He and his brother often fought to play the instrument, though there was "no question that music brought" the two together. In Daytona, they joined a YMCA group called the Y Teens, their first experience performing music with others. He and Duane returned to Castle Heights in their teen years, where they formed a band, the Misfits. Despite this, he still felt "lonesome and out of place", and quit the academy. He returned to Daytona Beach and pursued music further, and the duo formed another band, the Shufflers, in 1963. He attended high school at Seabreeze High School, where he graduated in 1965. However, he grew undisciplined in his studies as his interests diverged: "Between the women and the music, school wasn't a priority anymore."