Consumers Who Go to Extremes to Win Contests, Prizes

Entering thousands of sweepstakes can pay off—think a year’s supply of ice cream or a trip to Hawaii.

Happy Businesswoman
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"Two months ago, I won a thousand-dollar gift card at Macy's," says Zita, who considers her husband the sweepstakes hobbyist, but some of his interest in prizes has obviously rubbed off. "Thanks to Dick, I won the opportunity to carry the Olympic torch on the way to Atlanta for the summer games. His nomination, chosen at random, said he wanted me to carry the Olympic torch 'because he had been carrying a torch for me for years,'" she adds.

Of course, the hobby can get out of control. "I've seen contest players line up for miles for the chance to get a free tank of gas … and burn half a tank and three hours of their life doing it," says Smith.

Echoing that is Terri Lynn, a public relations specialist in Fort Lauderdale, Fla., who says, "I know people who enter contests all day long, every day, like it's their job. I just do it when I want to relax, like during the evenings and weekends."

Lynn got her first taste of winning a contest years ago when she was at a business luncheon and had her business card picked and won two tickets to South Korea. More recently, she entered a contest on Twitter and won free ink from Hewlett-Packard. Then, after snagging a $100 gift card to a grocery store, she was hooked. In the past two years, the fruits of her labor include 5,000 miles on JetBlue Airways and two concert tickets to see Paul McCartney.

[Read: 8 Painless Ways to Save Money.]

But few have arguably been as successful at winning contests as Wilman, who consults with companies, advising them on how to make their contests and sweepstakes better and more appealing. When she isn't blogging, writing, and advising clients on contests, Wilman is entering them, spending up to two hours a day on her hobby, and according to Wilman, since 2001, she has won more than a $250,000 in prizes, including movie passes, concert tickets, gift cards, clothing, beauty products, appliances, and 16 vacations. She says she even won the opportunity to meet the pop legend Sting.

"You have to find your balance, what works for you, and what you're looking for," advises Lynn. She never, for instance, enters contests she doesn't want to win. She often seeks out expiring contests—that way, she doesn't have to wait long for the prize to be drawn. She only sticks to legitimate contests, sweepstakes, and giveaways, advising people to avoid websites belonging to companies they've never heard of. Don't pay money to enter a contest, she emphasizes. When possible, she also recommends using Roboform, software that fills out the contestants' name, address, and other personal information.

Roboform or another tool that makes it easier to enter contests can be indispensable, says Lynn: "If you're filling out hundreds of sweepstakes every day and you don't use [an aid], you'd go out of your mind."