Marc Rigby was at work when he got the call. He’d just won an $8,000 trip for two to Tokyo, including the flight, hotel and $400 in spending money. A year earlier, he won a weekend in Nashville to watch a taping of the Grand Ole Opry. Since then he’s won scores of T-shirts, movie passes, free concerts, a jigsaw puzzle with his photo on it and a two-pound bag of candy. “Over the last three years,” says the 37-year-old director of business development at a Toronto technology company, “I’ve won almost $20,000 worth of prizes.”

So is Rigby the luckiest guy in Canada? Not at all. He’s just better at entering contests than most people, and you could be too.

Rigby’s life as a contest winner started when he realized that a $2 Lotto 6/49 ticket buys you only a 1 in 14,000,000 chance of winning the grand prize. In contrast, you can enter thousands of promotions such as the Electrasol Kitchen Appliance Makeover contest or the Samsung Ultimate Test Slide contest for free. The prizes may be smaller, but the odds you’ll win are much higher. “Now I probably spend about two or three hours entering 40 or 50 contests a week, about as much time as you’d spend on any other hobby,” he says. “I like the randomness of it. You can win tickets to movies that you might not have gone to see, and they all seem better when they’re free.”

To save time, Rigby says he uses websites such as ContestCanada.com and ContestHound.com, which list contests currently open to Canadians and link you directly to the entry forms. He also turns on the autofill function on his web browser, so that regularly-entered information is filled out automatically.

Carolyn Wilman, Canada’s self-proclaimed contest queen, goes a few steps further. The promotions consultant from Oshawa, Ont., says she fills out about 50,000 contest ballots a year. She has won more than $100,000 worth of prizes over the past five years. Her wins have included trips to Los Angeles, New York, London (England), Venice, and a memorable three-day Molson Indy prize pack which included all the Maple Lodge Farms chicken products you can eat. “I spend an hour or two entering contests every day,” she says. “I love it because sometimes you win things that you could buy, but they’re not really in your budget — and other times you can win stuff that no amount of money can buy.”

Wilman, who has self-published a book called You Can’t Win If You Don’t Enter (available at ContestQueen.com)
has even enlisted a software program called RoboForm (Roboform.com) that allows her fill out 50 ballots an hour. She wins between 100 and 160 contests per year, or about one contest every three or four days.

Though Wilman says that positive thinking, Feng Shui and even her IMLUCKY license plate play a role in her winnings, her statistics confirm Rigby’s assertion that it all comes down to the odds. Both Rigby and Wilman win more than 40 cents per ballot they fill out, which works out to something like $20 in prizes per hour they spend entering contests. In other words, you could make a living just by entering promotional contests — as long as you don’t mind sitting down to an occasional dinner of two pounds of candy.