One of its biggest investors was defunct Toronto brokerage Thomson Kernaghan & Co., which sank in scandal amidst its alleged involvement with several U.S. penny stocks. Its star chairman, Mark Valentine, pleaded guilty in a U.S. court to one count of securities fraud in 2004, and was sentenced to serve nine months under house arrest and four years probation.
Cyberoad may have crashed in the markets, but it provided a handy springboard for the launch of Bodog.com. Mr. Ayre won't say where he got the financial support to keep the company afloat: There are rare instances, particularly in his business dealings, where he insists on privacy.
"There is a long convoluted story that happened, but I'm not sure I want to share that with you. It's private. I mean, it's a private company," he said. "Everything that I do isn't for public consumption."
Regardless of where it got its money, the company has mushroomed, thanks in part to the dramatic rise of Internet usage and to the proliferation of websites in offshore havens, which are almost impossible to police.
Of course, Bodog's success has as much to do with its outrageous marketing tactics, which once included a fictitious CEO whose exploits were featured on its website.
When Mr. Ayre's alter-ego "Cole Turner" wasn't running Bodog, he was intrepidly fighting terrorists or cavorting in Southeast Asian karaoke bars. Few people found any of this believable, but it generated some buzz.
Mr. Ayre had his doppelganger "killed" in a duel three years ago, and unveiled himself as the public face of Bodog.
He says privately held Bodog is the fifth-biggest company of this kind. Based on these figures, Forbes valued him as the 746th richest billionaire around with a net worth of "at least" $1-billion.
Actually, he wasn't even supposed to land on the cover, he confides at the end of a two-hour dinner. Forbes had wanted to use fellow Internet-gambling entrepreneur Ruth Parasol, who refused the honour.
Mr. Ayre was only too happy to take her place. Yet there are still some forms of publicity he shirks. After the run-in with B.C. regulators, for example, he's got no interest in ever turning Bodog into a public company -- regardless of how many investment bankers pitch him on the prospect.
""Never. Never. Never. Never. I got cured," he said. "I'm an operations guy. I'm not a fancy . . . public company guy."