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Thousands of contests and sweepstakes are available online. Giant corporations and local businesses are handing out computers, jewelry, shopping sprees, vacations, smart phones, cars, houses, boats and cold, hard cash.

You can win small prizes (burger, T-shirt), unique prizes (walk-on role on a TV show) and incredibly useful prizes (a year's worth of health insurance).

Yes, there are scams out there, and we'll talk about ways to avoid them, but there are plenty of real chances, too. Just ask Michelle Troutt, who in five years has won 22 vacations, cash, and countless other items.

Her best win: $100,000 in a contest celebrating the 100th anniversary of Hershey's Kisses. The prize also included an appearance on a special segment of "Deal Or No Deal" back in 2007, with a chance to earn $100 million. (She didn't.)

Here's the beautiful part: The win was a "second-chance drawing." Because none of the three grand-prize game pieces was redeemed by consumers, the candy manufacturer drew its winners from 3-by-5 cards sent in by savvy sweepers.

"That's all I did: one entry," says Troutt, who lives near Fort Worth, Texas.

How can you get that lucky? Read on.

It's not just luck

First, a clarification: A contest requires some kind of "skill," even if that's just the ability to download a picture of your kid. A sweepstakes is strictly a game of chance, i.e., you don't have to do anything to enter except enter. However, I'll be using the words interchangeably, just as folks who call themselves "sweepers" also enter contests.

Second: It's not just luck. Serious sweepers know how to enter. They watch for local contests, which tend to have fewer entries. They pay close attention to the rules; for example, "a 150-word essay" does not mean 50 words, or 500 words.

Donna Freedman

Donna Freedman

They enter as often as they're allowed, which can mean daily. They recognize which contests probably won't be won outright and immediately enter second-chance drawings.

Such behaviors were once described as the "three P's": patience, persistence and postage. Although some old-schoolers still enter only by mail, the Internet has made it a lot easier to sweep.

Why would companies give all this stuff away? To get attention, of course. Contests and sweepstakes encourage brand loyalty, promote new items and attract potential customers.

Of course, they're also a great way to collect data. Some contest organizers require only a name and e-mail, while others ask for addresses, phone numbers and even information on buying habits. That's why you should open an e-mail account just for these entries.

"You do get spammed. There's no way around it," says Patti Osterheld of SweepSheet, who has won furniture, nearly three dozen trips, numerous savings bonds, a piano, a trio of iPod Touches, thousands of dollars in cash and a year's worth of gas, milk and Starbucks coffee over the past two decades.

Watching for red flags

Osterheld deletes, unopened, any e-mail whose subject line doesn't include the word "congratulations!"

But be wary of any "Congratulations!" e-mails for contests you don't remember entering. Many sweepers keep spreadsheets or other records of their entries (who could remember so many on his own?).

Those who subscribe to can use the site's "sweeps management system." This tool keeps track of what you've entered, notifies you of deadlines and reminds you to enter as often as you're allowed.

Other signs of scam contests are e-mails that:

  • Promote contests from other countries.
  • Are written in poorly spelled or ungrammatical English.
  • Ask for a bank-account number so your "winnings" can be deposited.
  • Require a credit-card number to pay shipping and handling for your prize.

"Sometimes the red flag is there, but people don't pay attention because they think they just won something," says Giancarlo Massaro of

The "If it seems too good to be true" rule applies, even to what looks like a reputable company. To wit: the Facebook gift card scam of spring 2010. If you have questions about a contest, go to the organizer's home page or Facebook page -- directly, rather than by clicking on an e-mail or social media link -- to see if it's legit. Hint: Ikea wasn't offering $1,000 gift cards.

How to find contests

Websites organize contests by category, prize or deadline. There's an app for all the contests on Facebook. You can use an online search engine to focus on social media giveaways. At least one site, Prizey, specializes in blog contests, which are often easier to win because of a relatively low number of entries.

Contests may be anchored to specific events, such as Black Friday or a holiday season. Or the engagement season: Apparently a fair number of people decide to get married between Thanksgiving and Christmas, so online jewelry retailer Blue Nile sponsored a contest called "Ring It, Sing It."

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That's how Indianapolis resident Perry Whan recently came to propose to his girlfriend, Michaela Maloney, at the opening bell of Nasdaq in New York. Blue Nile helped him design the ring, paid their airfare and accommodations, and threw in a rock song written about their love. (You can view the proposal here.)

Not a bad deal for a guy who previously thought that online contests were "unwinnable." But he was inspired by the assignment and won the judges' hearts with a 500-word essay (with photos) about his high-school sweetheart.

Not everyone wants to go to that much trouble. The Blue Nile contest received only 400 essays. Josh Tauber, of the search-marketing firm Wpromote, has run social-media contests that drew only 30 or 40 entrants.

"Your chances are really high," says the director of viral marketing, who's worked on giveaways of everything from coffeemakers to a Ford Fiesta. In fact, he's come to recognize certain people who enter contest after contest.