In 1986 demand for SMA skateboards had grown at an increasing rate which they struggled to meet. At 16, Kaupas impressed Engblom when he arranged a manufacturing and distribution arrangement with the much larger company, Santa Cruz Skateboards. It is claimed by some in the skateboarding community that Kaupas pioneered rail slide manoeuvres in the late 1980s while at a Pro-Am skate contest held in Oceanside, California. Kaupas stunned the crowd by attempting a board slide down a handrail. Although his attempt was unsuccessful, skating history was made. This was followed up when Kaupas and Gonzales performed what is considered the first legitimate rail slide and later with 50-50 grinds.