He honed his street skateboarding skills by utilizing his surroundings, preferring not to ride ramps or parks.
[5] With this cover photo, Kaupas began to receive more magazine coverage and recognition from professional skaters.
[2] Also in 1984, SMA released Kaupas's first pro-model skateboard, which infamously featured a panther image drawn by Santa Monica artist Kevin Ancell.
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.
In the film, Kaupas displayed an ability to ollie which far surpassed anyone else, and his part is considered to have paved the way for the new direction of skateboarding.
Kaupas along with fellow skater Jim Thiebaud, who was now skating for SMA, began a tour across America driving used Cadillacs.
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 then found work in design and art with clothing companies Quiksilver and Element Skateboards.
He has commissioned artists to interpret his original Santa Monica Airlines Panther graphic into their own vision.