In 1991 fellow pro skater Steve Rocco, who founded World Industries skateboards, approached Kaupas about starting his own line of skateboards. Kaupas left SMA and began 101 Skateboards. The company would become an outlet for Kaupas to employ his graphic and artistic talents. By 1992, 101 had become a major brand, however a broken ankle meant Kaupas' skating career was halted. While convalescing, Kapaus explored his artistic talents more and began to use computer graphics programs. He was soon asked to assist with the first issue of the Big Brother skateboarding magazine, which was also owned by World Industries. As World Industries and 101 Skateboards became more successful, scooping up many well-established pro skaters and new emerging amateurs, Kaupas lost interest. Kaupas received a call from Larry Flynt Publications who were interested in launching a new magazine entitled "Rage" and needed an art director. Kaupas left shortly afterwards however, again losing interest after a change in tone of the magazine.