How to Make Money

Enjoy Entering Contests? These Unusual Competitions Offer Great Prizes

Updated February 17, 2015
by Steve Gillman
Contributor

Yes, it would be nice to win a lottery or a million-dollar sweepstakes, but the odds of winning a Powerball lottery are 1 in 175 million, and Publishers Clearing House says the odds of winning their big prizes “tend to have odds of winning in the hundreds of millions.”

So you’ll have to be extremely lucky to win lotteries, which are based entirely on chance. But contests, which by legal definition require some skill, are another matter.

How to Make Money by Entering Contests

Just ask Matthew Fletcher, who shared his story on Free Money Finance. While eating Sabra hummus, he noticed a contest announcement on the container. The company asked users of their product to make commercials about it. Fletcher pulled out his camera, shot a video and won a trip to the Mediterranean plus a year’s supply of hummus.

That’s when he decided he might be able to pay down his debt by entering more contests. In the nine months prior to writing his post, he won contest cash and prizes totaling $12,338. Much of that came from doing videos. Fletcher says:

One of my best sources of winnings has been from the website Tongal. They are a commercial creation website. Through them, I’ve won over $11,000 by submitting concepts and commercials for Benjamin Moore, Lipton Iced Tea, Mattel, and Robert Half.

But he entered all sorts of other contests too. For one, he had to guess the cost to ship a stuffed tiger, and for another, he had to design a horse-themed birthday party for girls.

Fletcher advises reading the rules carefully and entering competitions that best suit your skills or interests. He warns that the contests which require you to get votes could get you ostracized from family and friends “for continually badgering them about voting.”

Entering unusual contests — ones that might have fewer people in the running — might also help your chances of winning. Here are a few ideas to get you started:

Pumpkin-Growing Contests

These contests, along with the pumpkins, get bigger every year. In one recent competition, a farmer in Rhode Island won $15,500 for a pumpkin that weighed in at over 2,000 pounds! Ordinarily the prize would be just $5,500, but the extra $10,000 was for breaking the seemingly impossible one-ton barrier. That monster of a pumpkin won at the Topsfield Fair in Massachusetts, but you’ll find similar contests around the country.

There are also pumpkin-carving contests, like the one at ThisOldHouse.com. Upload a photo of your creation and you might win a $500 gift card. Who would have thought you could make money with a pumpkin?

Ugliest Dog Contest

You may have seen some of these contestants show up on the evening news, because the World’s Ugliest Dog Contest has been around for more than 25 years. The most recent winner took home a $1,500 prize. The “skill” here is in properly presenting your ugly mutt.

Ugliest Face Contest

If your dog is too cute for an ugly dog contest, you can try for a prize for ugliness! But it takes skill to win the title of the world’s ugliest face, because it involves “gurning,” a technique that contorts your face into something scary and unrecognizable. The most recent winner, a man in China, is known in local media as the “King of Deformed Faces.” His prize: $10,000.

Look for ugly face contests around the world. Recently, there was even an ugly face contest online that paid a $500 prize.

Wife-Carrying Contest

This contest, originally a Finnish tradition, has been held at the Sunday River ski resort in Maine for 15 years, according to the official Sunday River website. To win, you have to be the fastest to carry your wife (or significant other) through a 278-yard obstacle course that includes a steep slope and muddy water. The prize is your weight in beer and a dollar amount five times the weight (in pounds) of your wife.

Tip: For a bigger profit, ask your wife to drink a quart of water before getting weighed in. Those two pounds will add $10 to your prize when you win.

Cheese-Rolling Races

The traditional cheese-rolling race on Cooper’s Hill in Gloucestershire, England was so dangerous, it was suspended for years before organizers brought it back in 2014. It isn’t clear if the winner gets more than a roll of cheese and possibly a hospital bill, but at the Canadian Cheese Rolling Festival winners take home the cheese and a $500 gift card. They also get two ski season passes for Whistler Blackcomb, the ski resort where the event takes place.

Fantasy Fishing Contest

Unlike competitions where you have to actually catch fish, with FLW Fantasy Fishing, you stay home and create your dream team of competitors who participate in various fishing events. When your team members take a prize, you get points. Get enough points and you can win one of 50 prizes that are awarded. One recent winner took home $10,000.

Contests You Might Want to Avoid

The weirder contests can be fun — at least to watch. But sometimes they can be dangerous. Here are a few examples of contests you might want to avoid.

Shin-Kicking Contest

This long-time competition in England involves you and your opponent kicking each other in the shins. Ouch! And it appears that the most recent winner got only a small silver chalice to bring home, along with a possibly-broken toe.

Insect-Eating Contest

It was a staple on the television program “Fear Factor,” but eating insects can be dangerous. One man recently died during a bug-eating competition in Florida. It isn’t clear how many cockroaches and worms he ate, but had he won and survived, all he would have received was a python.

Hot Dog Eating Contest

Forbes reports that Nathan’s Famous International Hot Dog Eating Contest has been around for 99 years. The organization Major League Eating governs more than 50 competitive eating events, so these contests have certainly become popular.

But Fox News reports that Joey “Jaws” Chestnut had to eat 61 hotdogs (with buns) to win this year’s contest. That can’t be healthy. Then again, maybe it’s worth the health risks; Forbes says that Chestnut enters about 25 eating contests per year and makes over $200,000 annually from “event purses, appearance fees and other sponsorship income.”

How to Find Contests

If you want to enter a few contests, unusual or not, and you search online for “contests” or “list of contests” you’ll get a bunch of sweepstakes websites. Instead, Google “list of contests -sweepstakes” (the “-” symbol excludes sweepstakes).

You can also search for specific niches according to your skills. Add the year to weed out many old results. For example, search for “sports contests 2015″ or “photo contests 2015″ and the results will include some relevant events that have deadlines in 2015. To find the more unusual ones, I entered “interesting contests 2015″ and the results included these:

Innovation Contests: There are many prizes available in competitions for invention ideas.

Rube Goldberg Machine Contest: In this classic contest open to students from middle school through college, contestants build elaborate and funny machines to do simple things.

GW Business Plan Competition: This competition, with the most recent deadline in early 2015, allows you to present your idea for a new business venture. It offers more than $100,000 in prize money.

Eyewear Design Contest: Design a better pair of glasses and win 2,000 Euros (about $2,500) for first place, 1,000 Euros for second or 500 Euros for third.

There were also poster contests and writing contests, and these were all from just the first page of results.

Your Turn: Do you think you could win money in one of these contests?

by Steve Gillman
Contributor for The Penny Hoarder

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