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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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 and 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.