Everyone loves a winner and Calvin Ayre would seem to be the biggest winner around right now. The 44-year-old scion of a Prairies pig farmer loves to tell how he pulled himself up by his bootstraps to land, improbably, on the cover of Forbes magazine’s annual billionaires issue this month.
“I’m a farm boy from Saskatchewan. You’re never going to get that out of me,” said Mr. Ayre, red wine in hand, as he met a Globe Rubah4d and Mail reporter in a swanky Beverly Hills hotel lobby. The handsome, Costa-Rica-based entrepreneur still betrays his Canadian roots, capping his sentences with an obligatory “eh?,” but now bills himself as “the personification of a new American dream.”
You may have never heard of the Internet-gambling site Bodog.com, or its founder. In fact, just a few years ago, not many people had. But Mr. Ayre is now regarded as an Internet age Hugh Hefner, and one of the leaders in the exploding Internet gaming sector. He is a public relations wunderkind, routinely blitzing the U.S. media with images of bikini models and stories of his own bad-boy-billionaire persona.
Yet when it comes to self-promotion, Mr. Ayre is as selective as he is relentless. Like Jay Gatsby, the fictional hero who cleverly crafted his own rags-to-riches story, Mr. Ayre tends to gloss over some crucial details.
Such as how, a decade ago, he was a disgraced B.C. penny-stock executive. In 1996, a provincial securities watchdog slapped him with a 20-year trading ban and fined him for “misrepresentations.”
It was a nadir for the current Forbes cover boy, who figures he was $100,000 in the red at the time. It is not a chapter of his life he likes to discuss.
“Canadians are funny,” Mr. Ayre …