STOCK IMAGE: Enter To Win on Asphalt Road, Man standing Above the Title Ready to Walk. (Getty Images/iStockphoto) (stevanovicigor)

You’ve heard of making your own luck. What if I told you you could do just that and start winning contests and sweepstakes regularly? That’s exactly what “sweepers” do. Sweepers are people who enter contests and sweepstakes as a hobby. They make their own luck by entering a lot. Volume is the key.

Carolyn Wilman of Ontario, Canada, is a sweeper and author of "How To Win Cash, Cars, Trips and More." She estimates she's won more than a quarter of a million dollars worth of prizes. Some of her favorites:

• A Kindle

• A big basket of Elizabeth Arden makeup

• Two portable blenders

• Tickets to a Rihanna concert

• A chance to meet Sting backstage

• Free pizza for a year

• Two $2,000 shopping sprees

• A trip to London to attend a Harry Potter party

• Going to the Winter Olympics

• A two-week trip to Europe

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So how much time does she spend entering contests to win such amazing prizes? “I recommend spending one to two hours a day entering contests and sweepstakes,” Wilman said. “That’s enough to win plenty, but not so much you cut into work, family time and other obligations.” In those couple of hours a day, Wilman estimates she submits about 36,000 entries a year and wins about 1 percent of them. “It truly is a numbers game,” she said. “You can’t win if you don’t enter. And the more you enter, the more chances you have to win.”

To enter in such volume, Wilman and other sweepers leverage technology. First they find out about hundreds of available sweepstakes and contests from websites like Sweepstakes Advantage and Sweepstakes Fanatics, which list legitimate giveaways and sort them by entry frequency and prize type. They also subscribe to newsletters such as Sweepsheet and I Win Contests, for similar information. Most websites and newsletters are free, but you can choose to upgrade to a premium membership for about $30 to $50 a year.

The next contest-entering innovation is auto-complete software. Some Web browsers, including Chrome and Firefox, store your name and address and help you fill out forms with a single click. Wilman prefers software called Roboform, which she says has more features. She estimates auto-complete software cut her contest-entering time in half and points out that it eliminates typos that can disqualify you. "Auto-complete" software is different from "auto-submit" software. The latter promises to enter thousands of sweepstakes on your behalf but is prohibited by most contest rules.

Wilman’s own innovation is her method of sorting contests into folders. “When I first started entering contests and sweepstakes, I would often get confused and enter one that was already over or enter more times than was allowed,” she said. Now she enters one-time sweepstakes and puts them out of her mind. But for sweepstakes that allow multiple entries, she creates daily, weekly and monthly folders to keep track of how often she is allowed to enter. Then she enters as many times as she can for herself, friends and family.

She's not alone. There are "sweepstakes clubs" all over the United States and Canada where sweepers meet to trade tips. At a sweepstakes club meeting in Reisterstown, Md., members listed everything they had won since the last monthly meeting: Twelve Lindt chocolate bars. $30 worth of free makeup. Three movie passes. A one-gallon tailgate jug. And the biggie at this particular meeting: $500 in cash. The club awarded that member a prize . . . for winning the biggest prize!

Tech has taken the work out of couponing. Here’s how to save big with little effort.

Sweepers have techniques for improving their chances of winning. Here are some of them:

Crinkled paper: If it's a paper drawing, crinkle your entry slip or fold it like an accordion to make it easier to grab.

Colorful envelopes: If it's an envelope drawing, send in large, colorful envelopes.

Short entry periods: Choose contests with short entry periods, because fewer people are likely to enter.

Entry limitations: Go for sweepstakes with lots of limitations on your location, age, etc., for the same reason.

Many prizes: Select contests with great second and third place prizes, so that if you don't win the grand prize, you still have a chance of winning something good.

Good prizes: Focus your efforts on contests with truly valuable prizes or prizes that are meaningful to you.

People often call Carolyn Wilman and others “professional sweepers,” because they put so much time, technology and strategy into it, but she rejects that label. “I wish I could earn my living winning sweepstakes,” Wilman said. “But I couldn’t pay my rent if I had to rely on prizes. Winning just enhances my life.” Sweeping is also a popular hobby with people who aren’t working, because it provides them a path to possessions and experiences they couldn’t otherwise afford.

Companies create sweepstakes as a marketing tool to build excitement about their products. Wilman now consults with brands on how to improve their contests and coaches individuals on how to win those contests. So far, she estimates her proteges have won about $10 million worth of prizes — including a Ferrari, $80,000 in cash and a house.

They’re making their own luck.

Elisabeth Leamy hosts the podcast "Easy Money" and is a 25-year consumer advocate for programs such as "Good Morning America" and "The Dr. Oz Show." Connect with her at and @ElisabethLeamy.

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