Wales has been called "the father of the Noughties” in relation to his role as founder of Project Naughtie, a quixotic 1999 grassroots campaign to name the decade lasting from 2000–2009 the "Naughties". The word Naughties, often spelled Noughties, has since been adopted by much of the international press.
At the age of nineteen, Wales launched his first business, Nice Enterprises, described as "the world's first mail order flattery service." A year later, he co-published Fatplastiscene magazine, the first issue of which is in the collection of the National Gallery of Australia. In 1986 Wales became host of the ABC TV show Edge of the Wedge.
During the 1980s he was a frequent contributor to Australian radio station Triple Jay, providing commentary on pop-cultural issues, including a live report from Berlin as the Berlin Wall fell, and a comic strip featuring Guru Adrian for the station's fanzine, Alan.
Wales moved to New York to become a painter in 1989 and spent the 1990s showing at various Manhattan and Australian galleries, including Roslyn Oxley 9 and Sherman Galleries. During this time he also worked on content creation projects for MTV, Fox and Disney. Several companies, including Hanna Barbera, Fox Television, and MTV, have optioned Wales's creation Guru Adrian with a view to building a television show around the character; however, each project was eventually shelved.
In 1998 Wales and Australian dancer Catherine Hourihan launched the Red Vixen Burlesque, a popular downtown New York attraction that is now seen as an early progenitor of the burlesque revival movement.
On 18 May of the same year New York magazine carried a story about Wales's position as "official pinsetter" for the unmechanized antique bowling alley that exists beneath the Fifth Ave mansion that houses the famed Frick Collection. The article reported that Henry Clay Frick had had the underground two-lane alley constructed in 1914 for his own amusement. By 1998 the lanes were being used for the benefit of museum trustees, and Wales, in spats and Edwardian costume, had "perfected the technique of resetting the pins and then quickly ducking out of the way."
In 1999 Wales initiated Project Naughtie, a grassroots campaign to name the 2000s decade the "Naughties" with Geoff Seelinger and Matt Frost of Fondue Media. The campaign ran under the motto "Eighties, Nineties, Naughties."
That same year, Wales became Cultural Forecaster for Toyota, tracking and predicting trends for the automaker's design division. Known for pithy social commentary, he told Details magazine (April 2001) that "Fake is the new real." In 2000 he launched Ministry of Culture, a research, strategy and content creation firm.
In 2008, Wales and filmmaker Morgan Spurlock launched the website Cinelan, described by The Hollywood Reporter as a "film content publisher."
More recently, Ministry of Culture has created a viral campaign claiming to resurrect an ancient Welsh temperance movement called Prudent Boozers.
Since the 1999 launch of Project Naughtie, Naughties (or Noughties, as it is more commonly spelled) has slowly gained traction among sectors of the international press as a term for the decade lasting 2000–2009. The word is currently used by CNN.com in the US, BBC.com in the UK, and a host of Australian publications, including the Sydney Morning Herald. A December 2009 article for Murdoch news site news.com.au referred to Wales as the “father of the Noughties” in relation to his role as founder of Project Naughtie.