Craig began his career as a researcher for the Canadian Broadcasting Corporation's This Hour Has Seven Days.
In 1999, he launched iCraveTV, a controversial website which offered streaming broadcasts of television stations.
He shut down the website the following year after a copyright infringement lawsuit from the American broadcasters whose signals were available on the service.
[1] He acquired PrideVision, Canada's LGBT television network, in 2004, and announced plans to improve the channel's cable distribution by separating its adult entertainment and general interest programming onto two distinct channels.
In 2006, Craig sold his interest in OUTtv and HARDtv to Shavick Entertainment and Pink Triangle Press.