How to win online contests

A few years ago, I interviewed a group of "sweepers," folks whose hobby is entering contests and sweepstakes. They routinely won things like cash (as much as $100,000 at a clip), savings bonds, jewelry, tech items, vacations, cars, furniture, toys, concert tickets and free gasoline.

My favorite was marketing consultant Noah Fleming, who for a time entered up to 30 contests a day. Here's a sampling of what he scored in just two years: a 46-inch LCD television, a home theater system, DVD box sets, a Wii, a Flip Mino HD camera, two Xbox 360s plus games, an all-expenses-paid trip to the Montreux Jazz Festival in Switzerland, concert tickets, a 20-inch iMac, an autographed hockey jersey, an iPod, a Tassimo coffeemaker and two Dell laptops.

But that's not the best part.

As a Canadian, Fleming didn't have to pay taxes on his winnings the way his neighbors to the south do. It was all his, and it took only about 15 minutes per day.

"I was able to do this at the same time I was catching up on blogs and sipping on my morning coffee," he says.

That's because the Internet has made finding and entering contests and sweepstakes incredibly easy. Back in the day, sweepers lived and died by "the three Ps": patience, persistence and postage. These days it takes only a few strategic keystrokes.

Want a shot at winning? Read on.

Improving the odds
Although I'll be using the terms interchangeably, a "contest" requires some type of skill (often as simple as downloading a picture) whereas a "sweepstakes" is purely a game of chance.

• Bing: Origin of the word "sweepstakes"

Sweepers often enter both. One woman I interviewed does up to 400 contests every day. Programs like RoboForm make filling out all those entries a cinch.

The truly dedicated improve their chances in other ways, too. They know it's often easier to win local contests and blog-based giveaways than a nationally advertised sweepstakes. You can search for blog contests at a site called Prizey.

Second-chance drawings also have relatively few entries, so savvy sweepers type "second chance drawing" into online search engines or set it as a Google alert. (Post continues below video.)

Where else do they look?

• At an app that lists all Facebook contests.
• In sweepstakes newsletters like SweepsU.com, This N' That and SweepSheet.
• On websites like SweepsGoat and Online-Sweepstakes.c​om.

Companies sponsor contests to draw attention to their products and services, promote new items and encourage brand loyalty. But they also want your contact information, so create an e-mail address just for contests. Even if you don't win, you'll be hearing from them.

When a sweep is a scam
The Internet is rife with fraudsters, so heed these tips from the contest pros:

• Be super-cautious about "Congratulations!" emails for sweepstakes you don't recognize. (Diehard sweepers keep spreadsheets or other types of records.)
• Alerts for contests from other countries are best deleted. So are any with poor spelling and grammar.
• It's a scam if you're asked for bank account info or a credit card number.
• Should you have questions about a contest announcement, visit the sponsor's home page or Facebook page -- and do it directly, rather than clicking on a provided link.
• Other uses for prizes include giving them as birthday or holiday gifts, selling them on eBay and donating to toy drives and charities.
  
• Finally, remember that you must pay taxes on your winnings. Pay as you go, because the Internal Revenue Service will find you.

Readers: Do you enter contests and sweepstakes? Have you ever won?

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