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In 1991 fellow pro skater Steve Rocco, who started 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 and Kaupas was still actively skating, however this would change after he suffered from a broken ankle.
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.

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