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In 1991, World Industries skateboards founder and fellow pro skater Steve Rocco approached Kaupas about collaborating on a new line of skateboards.
In order to start 101 Skateboards, Kaupas left SMA.
Kaupas hoped that by starting this business, he could put his artistic and design skills to use. In the early 1990s, 101 became world renowned for its pioneering video content.
For the six or seven years that One-O-One Skateboards was in business, its team featured top-tier skateboarding professionals like Natas Kaupas, Gabriel Rodriguez, Eric Koston, Adam McNatt, Clyde Singleton, Gino Iannucci, Jason Dill, Kris Markovich, Andy Stone, Leigh Peterson, and Marcus McBride.