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Consumers Who Go to Extremes to Win Contests, Prizes

Geoff Williams

Extreme couponing, where people spend hours and hours trying to find as many coupons as possible to buy and save as much as possible, may be on its way out as a hot trend. But reality TV producers should start looking at the pastime of extreme contesting--that is, people who enter every contest, sweepstake, and giveaway they can find.

During the 1920s, endurance competitions that offered cash prizes for those with the most stamina or skill reigned supreme. Charles Lindbergh, in fact, may never have flown across the Atlantic if it weren't for a $25,000 cash prize as motivation. By the 1950s, it was common for companies to run contests, such as the Pillsbury Bake-Off that began in 1949 and is still going strong, says Carolyn Wilman, author of the book You Can't Win If You Don't Enter.

"Many of the contests had questions that you had to answer in 25 words, and they had to be judged, and it got very expensive because they would get thousands of entries in the mail that had to be weeded through," Wilman says. "So they started doing sweepstakes where people would enter but not have to give anything that was judged, which made it easier, although a lot of contesters freaked out because their hobby disappeared."

If you're already confused, wondering what's the difference between sweepstakes and a contest, any "sweeper" will tell you contests involve skill, like coming up with a slogan or a jingle for a product. For sweepstakes, you simply submit your name.

[Read: The Best Couponing Strategies for the Everyday Saver.]

Now, in the Internet age, people are bombarded by contests and sweepstakes while surfing the Web. "Brands are hyperactively seeking to entice consumers to become fans and followers to their social mediums, and more often than not, it comes in the form of 'Like us for a chance to win...' This has exponentially increased the number of prize-winning opportunities available to those who are willing to 'friend' or follow a brand [on Facebook]," says Sean Smith, president and co-founder of Third Street Attention Agency, an advertising agency in Chicago. Before that, he spent 20 years in radio as a DJ who gave away so many prizes he was dubbed the "Prize Doctor."

"In all cases, the chance to win a prize is now but a click away, which is a massive sea-change from the days of having to put a stamp on an envelope," says Smith.

With just a few clicks, you can find many sites like SweepstakesToday.com and LuckyContests.com offering chances to win prizes. There's even an annual sweepstakes convention, which will be held this June in Salt Lake City.

It's easy for a bystander to scoff at those who spend their time at their computer or tablet, trying to enter every contest--until, that is, they tell you what they've won. Jerry Huber, a telephone technician in Jefferson, Ga., who is now on disability due to poor health, has been entering sweepstakes for six years. He typically enters about 350 a day, but for a while he was entering as many as 600 until he decided to only chase after prizes worth $100 or more. He says he would enter 1,000 a day if he could find enough that fit that criterion.

Huber says he usually wins one major prize a year, like the 46-inch Samsung TV he scored, and about 40 minor prizes, such as a hat or T-shirt. Some of the bigger prizes included an Xbox, an iPad, and $150 of ladies' undergarments, which he gave to his daughters. He's also won gift cards ranging from $5 to $2,700. And about a week ago, he reeled in $150 worth of dog food and supplies for his yellow lab, Heidi.

[Read: Your Month-to-Month Guide to Great Sales.]

Zita Christian, a wedding officiate and romance novelist in Manchester, Conn., says her husband Dick has been entering sweepstakes for more than 30 years.

According to Zita, Dick has documented his winnings of more than 1,500 prizes in a number of three-ring binders. She says the prizes have run the gamut, from T-shirts and candy bars to a pool table and a year's worth of ice cream, all the way up to trips to Hawaii for the Pro Bowl and a vacation to a ski lodge in New Hampshire.

"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."

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