In 1992, after reading a newspaper article about a Caribbean-based company offering betting services over the telephone, Ayre concluded that gambling was tailor-made for the internet.

[8] Having taught himself network design by studying Cisco Systems manuals,[8] Ayre converted his Vancouver-based Internet incubator company into a software support firm for online gambling, which became Bodog.

He chose the appellation like a major corporation would pick the name of a new car or brand of soft drink: it had to have six letters or less, be easy to spell and remember, have some personality and be unlike any competitor's moniker.

[14] Ayre chose to make himself the focus of Bodog's marketing strategy, creating a public profile designed to showcase the trappings of a jackpot-winning lifestyle.

[8][17][18][19] In a 2009 interview,[20] Ayre stated that following the passage of the Unlawful Internet Gambling Enforcement Act (UIGEA) in 2006, the organization that he led and that had been accepting customers from the United States withdrew from that market, instead licensing the brand to the Morris Mohawk Gaming Group, which then operated its own online gaming website servicing the US under the Bodog brand until December, 2011.

In 2003, Ayre organized BodogConference.com in Las Vegas for sports handicappers, at which National Football League Hall of Fame quarterback Joe Montana was a special guest.

In March 2006, filming of party scenes for the first-season finale at Ayre's compound outside San Jose, Costa Rica, was raided by an estimated 100 police who were under the mistaken impression gambling was taking place.

[28] The April 2007 Clash of Nations finale in St. Petersburg, Russia, was attended by Russian President Vladimir Putin, former Italian prime minister Silvio Berlusconi and actor Jean-Claude Van Damme.

Antigua and Barbuda Prime Minister Gaston Browne called Canada Place, which features a solar panel array, "easily the most impressive building on the island, hands down.

Ayre also noted that the US Attorney had seized Bodog.com, a domain that had been dormant since the Bodog brand revoked its licensing agreement with MMGG the previous year.

[7] In September 2017, think tank Democracy Institute published Patrick Basham's case study[40] slamming US trade hypocrisy over online gambling dispute with Antigua-Barbuda.

[41] The study states that Ayre's conviction ran afoul of the WTO's ruling as to America's General Agreement on Trade in Services obligations.

"[43] The government of Antigua and Barbuda welcomed Ayre’s vindication as part of the failure of the US to comply with World Trade Organization ruling on Internet Gaming.

"[45] In June 2016, Andrew O'Hagan published a writer's account of the background behind Craig Wright publicly asserting himself to be Satoshi Nakamoto, the inventor of Bitcoin cryptocurrency, which made the news in May 2016.

He revealed Ayre to be part of the business operation behind this affair, possibly even its ultimate organizer and the financial backer of the $30 million acquisition and development of Craig Wright's assets.

The foundation has supported needy families, elementary schools and physical rehabilitation centers in Costa Rica, worked with groups to combat bear bile farming in Asia, and provided funding to enable individuals to pursue higher education.

[52] In 2006, Ayre produced Bodog Salutes The Troops, a weekend of entertainment for US military personnel in Hawaii, footage of which appeared in a one-hour special on Spike TV.

The event, which consisted of a poker tournament and a live musical concert featuring Snoop Dogg, was intended as a benefit for the Fisher House Foundation.