Chums from his school days remember this much about Calvin — if you beat him in a foot race, he'd make sure he'd whip you the next time out. He didn't like losing.
He was always a committed partier, but his academic interest wavered. He enrolled at the University of Waterloo to become an optometrist, but wound up with a science degree. He joined the University of Western Ontario law program, but flunked out. "I was expelled actually, " Mr. Ayre said. ". . . I might not have been quite smart enough to be a lawyer."
But he had a head for business. He set out for the West Coast and earned an MBA at City University in Seattle, graduating in 1989. Less than nine months later, at 29, he was appointed president of a small Vancouver-based company called Bicer Medical.
It looked like a promising start, but his aging Scottish grandpa wasn't impressed.
"Fred wasn't happy with the business he was in," recalled Helen Wilson, Mr. Wilson's second wife, in a phone interview.
"He didn't think it was completely on the up and up."
In 1996, the British Columbia Securities Commission fined Mr. Ayre $10,000 in a ruling that prevents him from trading securities on the Canadian Venture Exchange or acting as a director of a B.C. public company until 2016.
As part of an agreed settlement, Mr. Ayre admitted to making "misrepresentations" concerning millions of Bicer shares he controlled. The BCSC ruling says he "traded through accounts in other persons' names at several brokerage firms."
He had also breached an undertaking he gave shortly after joining Bicer — that he would stay away from a character named Erich Brunnhuber.
(Records show that, at the time, Mr. Brunnhuber was supposed to be in the middle of a seven-year jail term he was serving for multimillion-dollar mining-stock fraud in 1984. Yet he had been allowed out of prison, and briefly went to work in Bicer's marketing department, before a judge allowed him to visit his ailing mother in Germany. Mr. Brunnhuber never returned, and is still a fugitive .)
For his part, Mr. Ayre has moved on. Bicer, he said, was the biggest mistake of his life.
"It's the first thing I did out of university. I had no idea what was going on," he said in exasperation. "I don't want to talk about this Rubah4d any more. You are asking me about something that happened 15 years ago that has nothing to do with who I am today. I am saddened by that."
The unlikely ascent of Calvin Ayre, according to the autobiographical entry on his company's website, is an almost archetypal account of the self-made man. After finishing his MBA, he sold his worldly possessions for $10,000 and used the money to create a software firm. Then he envisioned an even grander scheme: using the nascent Internet to tap into the sports gaming industry.
Ten years and $1-billion later, Mr. Ayre sounds almost modest when he declares, "the gamble paid off."
It's a good story. However, in an interview, Mr. Ayre acknowledged he was involved in plenty of ventures during the 1990s, many of which didn't fare so well. "Most of my businesses have actually failed," he said. "That's how you learn."
Still, his past dealings are not entirely clear, and Mr. Ayre would just as soon not talk about some of them.
Around the same time he was working at Bicer, in the early 1990s, he began developing connections in the Vancouver stock markets, joining nine different corporate boards. He also had a hand in starting several companies, including Calvex International (which once planned to build a $100-million trade centre in Ho Chi Minh City) eBanx, Ecomm Relationship Technologies, and most crucially, Cyberoad.com, a software gaming company.
"There's no point in me talking about Cyberoad," Mr. Ayre said dismissively in an interview. "It wasn't my company, it was only one of a number of customers I had."
In U.S. regulatory filings, however, Mr. Ayre is described as the "creator and visionary" of Cyberoad. The filings say he gave up his CEO's title shortly before the company obtained a stock listing in the U.S. "over-the-counter" market in the spring of 1999, and began acting as a consultant.
At this point, Mr. Ayre was involved in a complex web of interconnected companies, many offshore, that are difficult to distinguish from one another. Take Cyberoad as an example: There were three different companies with that name, one based in Ireland, another in the Isle of Man, and the eventual public company, Cyberoad Corp., based in Florida.
It's not clear how much money, if any, Mr. Ayre made off this venture. However, regulatory records show that Cyberoad paid its Irish subsidiary nearly nine million shares of the company when it went public.
Cyberoad itself was not without controversy. Shortly before Cyberoad went public, its stock was hovering at a mere 62 cents. Just over a month later, it had skyrocketed to $6.88 a share, and was the subject of higher than average trading. Then came the slide. The stock quickly deflated, dropping to 12 cents by the summer of 2000. Since then, it hasn't been worth more than a few pennies a share.
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."
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