Prior to gaining attention in Australian media, he was drafted as a tall forward by the Hawthorn Football Club and intended embarking on a career as an AFL footballer, but was cut after less than one season partly due to chronic injury.
Some time after becoming the second (and final) winner of Race Around the World, he joined the 3RRR Breakfasters, a radio panel show which had formerly featured personalities John Safran, Dave O’Neil and Kate Langbroek. He remained on the panel for six years before finishing to pursue his writing.
He is a regular panelist on the ABC quiz show, The Einstein Factor.
In 2005 his first novel ‘Players’ was published, a parody of Australian football variety show personalities. The novel became a critical success, and Wilson won the SMH ‘Best Young Australian Novelist 2006’. His follow-up book, ‘Australia United’, was a Gonzo journalistic diary of his travels with Australian soccer fans to the 2006 World Cup in Germany. He has also written four children’s picture books, 'Grannysaurus Rex', ‘The Thirsty Flowers’, 'Harry Highpants' and 'The Minister for Traffic Lights'. 'Harry Highpants' was selected for the prestigous White Ravens stand at the 2008 Bologna book fair.