Judkins organised his first sports event in 1975, the Coca-Cola Freestyle Skiing Contest. He fell out with his two partners and proceeded alone, vowing to never again team up with others for organising an event. After his time in Australia and London, his next venture into sport as a business was to set up Motatapu Canoes; the idea to do so came to him when he was kayaking the Motatapu River with his friend Peter Tocker. They had a high-profile launch of the company by the local MP, Warren Cooper, who attended as Minister of Tourism. Things went wrong during the launch and, according to Judkins, Cooper nearly drowned. But promotion has always been important to Judkins, and the publicity helped to get off to a good start. Aiming for greater things, they changed the name of the company to Outdoor Adventure Centre. Part of their plan was to offer private expeditions called 'Aspiring to the Pacific', and when he and Tocker did a test run, it took them twelve days to complete it. Somewhere on the Clutha River, the idea came to them that they should have started on the West Coast, so that the expedition went from coast to coast. It was the nucleus of the idea for the Coast to Coast adventure race that began several years later in 1983.