Last Thursday, Ron Tarter put $50 on a horse named Just Got Lucky in the fifth race at Toronto's Woodbine racetrack.
But the name didn't pay off. Just Got Lucky, which he had bet to win, placed third.
Mr. Tarter, 24, a business-school dropout who grew up in the Toronto suburb of Thornhill, is hoping for better luck with a much more ambitious wager he made last year. In fact, he is hoping to strike it rich in the controversial but booming international business of on-line gambling -- worth an estimated $1-billion (U.S.) to $2-billion a year at present -- through his Antigua-based Casino Affiliate Network (CAN).
Mr. Tarter abandoned his pursuit of an MBA at Toronto's York University last year, and with his parents as the two other shareholders launched his venture through a holding company called Sinsational Entertainment Inc., which is also registered in the gambling-friendly Caribbean island.
CAN's main Web site is http://www.cybersportsbook.com , but rather than being satisfied with running a few casino sites himself, Mr. Tarter instead decided that the real future lies in distribution.
He has concentrated on signing up Web site operators, or Webmasters, around the world, giving them the opportunity to add customized casinos with sports betting and games to their existing offerings.
They get to ride on the coattails of gambling software he licenses from Starnet Communications International Inc. and a gambling licence for which CAN is paying the Antiguan government $100,000 a year.
The operators pay nothing to join and keep 25 per cent of the losses incurred by any punter they sign up, no matter which CAN-affiliated site the gambler plays at. The betting is tracked by CAN, whose 15 employees handle all the accounting and other administrative functions for the network.
Mr. Tarter said he has recruited a startling 5,000 Webmasters since CAN went on-line 14 months ago and that there are now about 1,000 affiliate sites up and running. They, in turn, have signed up more than 100,000 on-line gamblers.
He thinks his business will get a whole lot bigger. "The potential is unlimited," he said from Thornhill during a week's vacation away from Antigua, where he now has resident status. "Any given affiliate can put up as many sites as they wish, so the number is exponential. There could be hundreds of thousands of sites."
Mr. Tarter wouldn't reveal how much it cost to get CAN off the ground, beyond saying that it would be "pretty hopeless" if anyone tried to emulate him with less than $1-million to play with.
He did say, however, that he financed the business with some help from his father and with gains he made selling stock in Starnet -- formerly based in Vancouver but now in Antigua -- that he bought with a bank loan while working part-time at investment dealer ScotiaMcLeod Inc.
He's cagey about CAN's financial results, too, saying only that its monthly revenue hasn't yet topped $1-million but that it is already profitable.
Mr. Tarter has made believers of some of the Webmasters who have signed on.
"It has worked out great for me," said Jeff Broughton, a freelance computer programmer who launched his affiliate site, http://www.playtheodds.com , in January.
Mr. Broughton, 27, a Canadian expatriate, is moving to Antigua from his current base in Holland. With minimal expense and effort, he said, he has watched as his profit hit $2,000 a month in March and $5,000 in June. "I hope to break the $10,000 mark in September," he added.
It's no secret why Mr. Tarter has based his business in Antigua and established residency there. It is illegal to operate an on-line gambling site in Canada and the United States; as a result, many industry players are located in countries such as Antigua and Costa Rica that actively court dot-com casinos.
Some on-line gambling concerns have attracted unwelcome attention from North American authorities. Starnet, where Mr. Tarter worked briefly as a marketer in Vancouver in 1998, became the target of a police investigation last year for allegedly distributing illegal pornography on the Internet, although it subsequently sold its "adult entertainment" business.
As well, in the first case of its kind, a U.S. judge two weeks ago sentenced Jay Cohen of San Francisco to 21 months in prison and fined him $5,000 for illegally operating an offshore Internet gambling business, Antigua-based World Sports Exchange.
Apparently anxious to avoid creating problems for his family or himself should he return home down the road, Mr. Tarter has taken other steps to minimize his business's connections with Canada. "We block all Canadian credit cards and deactivate any Canadian accounts."
The precautions do not surprise Ian Kerr. Now an associate professor of law at the University of Ottawa, he taught Mr. Tarter at the University of Western Ontario in London, where the Internet entrepreneur graduated top of his class in 1998 with a BA in media information and technoculture.
"He views on-line gambling . . . not as a criminal activity, but the kind of thing where the law has just fallen behind in terms of what kind of regulatory approaches are appropriate," Prof. Kerr said.
Similarly, his drive comes as no surprise to stockbroker Rob Saltsman, Mr. Tarter's boss while he worked part-time at ScotiaMcLeod during high school and university.
"He's the type of guy that when he gets something going, I'd bet with him," said Mr. Saltsman, who is now an investment dealer at Goepel McDermid Inc. in Toronto.
Mr. Tarter's talents weren't so obvious to begin with. He was bored with high school and was failing some of his classes.
But he fell in love with the financial business, where he ultimately graduated from gopher work to helping develop sales leads. "Here's a guy who was a bum and burned out, and all he had to do was find something he liked and he was a brand new guy," Mr. Saltsman said.
As it happens, CAN isn't Mr. Tarter's first gambling venture. He said he developed a taste for gambling in high school, and about six years ago, having made "a few thousand bucks" wagering through some offshore sports books, he and a friend took out a student loan and started selling a system for betting.
"But unfortunately, that was the year all the sports leagues went on strike," he recalled, "so it pretty much demolished us."
Assuming CAN manages to avoid demolition, Mr. Tarter said he hopes to cash out down the road either by going public or by selling out to one of the major bricks-and-mortar casino operators that he predicted will eventually push their way into the on-line arena.