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The women who win hundreds of sweepstakes per year

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Spend enough time online, and you'll come across some kind of contest or sweepstakes offering you a chance to win a prize. Most of us brush these off as  dangling carrots — veiled corporate attempts to collect our data and court free advertising. The odds of actually winning seem miniscule.

But a community of avid "sweepers" claim to have mastered the art of winning these sweepstakes. They consistently land hundreds of prizes year after year — vacation packages, cars, event tickets, electronics, and cash — and their hauls sometimes amount to tens of thousands of dollars.

Who are they? How do they do it? And are these contests too good to be true?

The "sweeping" community

Every year, an estimated 55 million Americans enter some kind of sweepstakes ( known as "competitions" in the UK or "contests" in Canada).

Though there are many ways to enter sweepstakes (mail-ins, call-ins, in-person drawings, and text messages) the majority of today's contests take place on the internet, where hopeful prize winners can participate via retweets, hashtags, Instagram photos, and digital forms.

For most entrants, it's a one-time submission — a hail-mary shot at winning a free prize. But for the so-called "sweeping" community, it's a way of life.

They gather in forums like Sweepstakes Advantage, subscribe to newsletters like I Win Contests, SweepSheet, and Sweeping America, and gather at conventions all over the world. In private Facebook groups, they swap strategy tips and tales of monstrous wins: $22k fishing boats, all-inclusive trips to Japan, and new cars.

A serious member of the sweeping community will enter anywhere from 20 to 300 sweepstakes every day, often utilizing sweepstakes aggregators, automated form-fillers, and Excel spreadsheets.

Though the community is mostly made up of women, the ease of digital contest entry has attracted a diverse spectrum of competitors, from college kids to retirees — all of whom claim that winning sweepstakes can be made into something of a science.

"I don't enter the lottery, or gamble, or take big risks," one long-time sweeper told The Hustle. "But with sweepstakes, I can pretty much guarantee I'll win."

According to an informal poll of 585 respondents, roughly half of all regular sweepers report winnings equivalent to $1,250 or more per year; a quarter win $3k+ in prizes.

What about that small 4% fraction that rakes in more than $12k per year in prizes? Are they just extraordinarily lucky or do they have some kind of system that increases their odds of locking down that dream vacation?

To find out, we spoke with several women who have collectively made more than $500k winning contests online.

The big winners

Diana "Di" Coke still remembers her first sweepstakes win.

It was the early 1990s and Coke, then in her 20s, was an unemployed music buff who couldn't afford tickets to the Glastonbury festival in the UK. One day, while flipping through a music magazine, she spotted a mail-in ticket giveaway.

"I stuck photographs of the bands on the back of a postcard and made it look exciting," she says. "My strategy was to stand out as much as possible."

She won. And then, she became addicted.

"It seemed like I was winning every contest I entered," she says: "Backstage passes, a guitar signed by Oasis, 365 bottles of beer — all by just entering these contests."

Today, Coke is among the UK's most successful "compers" (the English equivalent of a sweeper). The operator of a popular sweepstakes blog, she has made the hobby into a full-time job.

In her 20 years of sweepstaking, she's hauled in more than £300k (US $376k) in prizes, including:

  • A brand new VW Beetle
  • £35k in cash
  • £23k in product vouchers
  • Trips to Tokyo, Barcelona, Antigua, Cyprus, and Brazil
  • Front-row tickets to London Fashion Week
  • 7 straight years of Glastonbury music festival tickets
  • A washing machine, refrigerator, and dishwasher
  • 12 televisions
  • 5 iPhones
  • 9 iPods and iPads
  • Flying lessons
  • A year of free ice cream

On average, Coke enters around 300 online contests per month (about 10 hours' worth of work) and wins £1k in prizes.

In 2019 alone, she's won 51 prizes collectively worth £5,389 — everything from a trip to Mallorca, Spain on a private party jet, to a machine that shoots soccer balls. (She shared her spreadsheet of wins with us here).

Her strategy is simple: She primarily enters "qualitative" online contests that allow her to stand out in some way, like tweets or photo tags on Instagram.

"A lot of people maintain that [sweepstakes] are just pure chance," she says. "But the people running them aren't picking at random. They often go for the person who put in more effort than everyone else — the type of winner who would really appreciate the prize."

Case in point: She once won a trip to Florida by tweeting a photo of herself standing in the snowy streets of England in a bathing suit.

But not every successful contest winner plays that game.

Carolyn Wilman (AKA, the "Contest Queen") has raked in $250k in her sweepstaking career using a quantitative strategy based on sheer volume: 

  1. She creates a new email specifically for sweepstakes.
  2. She uses sweepstake aggregators (resources that list thousands of legitimate promotions in one location) to find form-based competitions.
  3. She uses software to auto-fill hundreds of entry forms with her information.

In a one hour-long sitting, with a few clicks, Wilman can enter more than 200 sweepstakes. The goal is two-fold: To enter as many contests as humanly possible, and to minimize the amount of time it takes to do it. 

"Luck has nothing to do with winning," she says. "It all comes down to effort and persistence."

Her persistence has paid off. In her best month, she won 83 prizes; in her best year, earnings topped $60k. Highlights include a $40k vacation package to the 2010 winter Olympics, a trip to London to visit the set of Harry Potter, and tickets to the British Open in Scotland.

"One time, I even won a meeting with Sting," she giggles. "He smelled so good."

What brands gain from sweepstakes

A marketer by trade, Wilman understands that the sweepstakes she enters come with loaded motives. "The companies and brands running these contests aren't doing it out of the goodness of their hearts," she says. "It's a business decision."

Sweepstakes are something of a win-win: You get a free prize, and the company running on the promotion gets brand exposure, sales, and customer acquisition.

Take, for instance, a Black Friday contest Kohl's ran on Twitter, where users had to retweet their ad for a chance to win a $20 gift card.

Kohl's gave out 1,000 $20 gift cards ($20k total), but the ad got 10,812 retweets. According to an estimate from the data analytics company SumAll, the value of a branded retweet is $20.37. So for a cost of $20k, Kohl's got roughly $220k in value — about 10x its investment.

This effect is called consumer-generated marketing (or user-generated content): By offering some kind of sweepstakes or prize through social media, brands are able to court millions of dollars worth of free advertising.

Of course, entering contests online comes with other potential costs to entrants.

The sweepstakes industry is rife with scammers and opportunists — and if you don't carefully read the fine print, the operator could use a prize as a ploy to gather and sell your data. (We previously wrote about the 'free car at the mall' scam, which does exactly this.)

In the US, entrants also have to be wary of taxes: Those dream home sweepstakes often burden winners with taxes that can amount to 40% of the home's value. And let us not forget the time when Oprah gave her audience members new cars, unintentionally saddling them with $7k in upfront bills. (Notably, competition wins in the UK aren't taxed.)

But avid sweepers read terms and conditions in their sleep — and for them, these risks are justified by the thrill of constantly winning.

How to win sweepstakes

We asked Coke and Wilman to pony up some tips for sweepstakes newbs. By following a few simple rules, they say you can dramatically increase your chances of winning more contests:

  1. The harder a contest is to enter, the easier it is to win. ("Contests that require a photo get far fewer entries." — Coke)
  2. Stay local. ("Restaurants, bars, and movie theaters regularly do giveaways where only local people can enter." — Coke)
  3. Always read the terms and conditions. ("You never know when they might sneak in some secret clause." — Wilman)
  4. Set up a dedicated email address for contests you enter. ("All it takes is one mistake, and they'll get your email for life." — Wilman)
  5. Use sweepstakes aggregators to find opportunities. ("They're a one stop shop, and they filter out the bad ones." — Wilman)
  6. Stay organized. ("Keeping track of everything you enter in a spreadsheet allows you to look for trends in your wins." — Wilman)

"At the end of the day, it's not gambling or Candy Crush; if you work hard enough at it, you can actually win fantastic little prizes without spending any money," says Coke. "It's thrilling — you never know what the next submission is going to bring."

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11 comments. Last comment 3 months ago by noise-gate.
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Pick3master3838's avatar - hiro bird.jpg

United States
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July 7, 2019
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Posted: July 15, 2019, 3:18 pm - IP Logged

Then you get a ton of email spam.

    Todd's avatar - Cylon 2.gif
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    Chief Bottle Washer
    New Jersey
    United States
    Member #1
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    Posted: July 15, 2019, 4:14 pm - IP Logged

    Then you get a ton of email spam.

    You really should read the article.  The first thing the woman recommends is, "She creates a new email specifically for sweepstakes."

     

    Check the State Lottery Report Card
    What grade did your lottery earn?

     

    Sign the Petition for True Lottery Drawings
    Help eliminate computerized drawings!

      Avatar
      California
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      Member #179467
      January 20, 2017
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      Posted: July 15, 2019, 4:35 pm - IP Logged

      Kind of reminds me of Helen Hadsell's story.  I have her book, "Contesting:  The Name it and Claim it Game"

        Sarge0202's avatar - m109
        Springfield, Ill
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        February 28, 2017
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        Posted: July 15, 2019, 5:50 pm - IP Logged

        I've been thinking about using Selenium to automatically play all the games/sweepstakes at pch.com.  The funny thing is, PCH is actually looking for a programmer to write/maintain/use Selinium to test their website.

        Don't believe everything you read on the Internet.    --- Abraham Lincoln

          grwurston's avatar - Lottery-012.jpg
          Win Today.
          bel air maryland
          United States
          Member #90247
          April 24, 2010
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          Posted: July 15, 2019, 8:49 pm - IP Logged

          A word of warning. A lot of sweepstakes are conducted by charities looking for a donation. Most of them ask for as little as $7 or $10. But once you enter a few, you will be put on a mailing list and will be bombarded with sweepstakes entries. Don't be surprised to get 30 or more a week in your mail box. A lot of them are scams. Look at the official rules to see who is sponsoring the sweepstakes.

          Here is a list of the 50 worst charities. What makes them the worst is how little money actually goes to the people they say they are helping, and is actually spent on salaries, fund raising, mailing donation requests, advertising, etc. Some may surprise you. Some may sound familiar to more well known charities. That is done on purpose, to fool you into thinking you are donating to the legitimate charities. It is all part of the scam they are conducting. Let the buyer, or in this case donator, beware.

          The Professionals

          Then there are the professional long term operations. They utilize direct mail or telemarketers to solicit millions of dollars in donations from unsuspecting individuals and businesses. Are you concerned you’ve already been scammed or just want to make sure you won’t be in the future? Here are some of the worst offenders:

          1. Kids Wish Network
          2. Cancer Fund of America
          3. Children’s Wish Foundation International
          4. American Breast Cancer Foundation
          5. Firefighters Charitable Foundation
          6. Breast Cancer Relief Foundation
          7. International Union of Police Associations, AFL-CIO
          8. National Veterans Service Fund
          9. American Association of State Troopers
          10. Children’s Cancer Fund of America
          11. Children’s Cancer Recovery Foundation
          12. Youth Development Fund
          13. Committee For Missing Children
          14. Association for Firefighters and Paramedics
          15. Project Cure (Bradenton, FL)
          16. National Caregiving Foundation
          17. Operation Lookout National Center for Missing Youth
          18. United States Deputy Sheriffs’ Association
          19. Vietnow National Headquarters
          20. Police Protective Fund
          21. National Cancer Coalition
          22. Woman to Woman Breast Cancer Foundation
          23. American Foundation For Disabled Children
          24. The Veterans Fund
          25. Heart Support of America
          26. Veterans Assistance Foundation
          27. Children’s Charity Fund
          28. Wishing Well Foundation USA
          29. Defeat Diabetes Foundation
          30. Disabled Police Officers of America Inc.
          31. National Police Defense Foundation
          32. American Association of the Deaf & Blind
          33. Reserve Police Officers Association
          34. Optimal Medical Foundation
          35. Disabled Police and Sheriffs Foundation
          36. Disabled Police Officers Counseling Center
          37. Children’s Leukemia Research Association
          38. United Breast Cancer Foundation
          39. Shiloh International Ministries
          40. Circle of Friends For American Veterans
          41. Find the Children
          42. Survivors and Victims Empowered
          43. Firefighters Assistance Fund
          44. Caring for Our Children Foundation
          45. National Narcotic Officers Associations Coalition
          46. American Foundation for Children With AIDS
          47. Our American Veterans
          48. Roger Wyburn- Mason & Jack M Blount Foundation for Eradication of Rheumatoid Disease
          49. Firefighters Burn Fund
          50. Hope Cancer Fund

          This list was put together by the Tampa Bay Times and The Center for Investigative Reporting based on federal tax filings for the last 10 years. Charities are broken up into five main categories: children, cancer, police/law enforcement, veterans, fire and other. These fifty charities account for more than $1.35 Billion in donations. Of that, $970 million went not to victims, but to the people who collected the money.

          "You can observe a lot just by watching." Yogi Berra, Hall of Fame baseball player.

          The numbers will tell you what numbers to play. Pay attention to the numbers.

          Every lottery system can be improved. If you're not winning almost every day, yours can be made better.

            Nikkicute's avatar - wi lotto3.jpg
            Wisconsin
            United States
            Member #123286
            February 17, 2012
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            Posted: July 15, 2019, 10:04 pm - IP Logged

            My biggest prize was a 50inch television, some Sauve shampoo and Skinny Cow snacks, when I first

            started sweeping years ago but then I stopped. 

             

            The smaller prizes just come in the mail, it was fun, may get back into it again.

              Coin Toss's avatar - shape barbed.jpg
              100
              Zeta Reticuli Star System
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              Posted: July 15, 2019, 11:57 pm - IP Logged

              grwurston,

              Thanks for posting that list.

              I saw another one (maybe from www.charitywatch.org) that said the Make A Wish Foundation is real, but a lot of bogus charities try to play on that name and except for Make A Wish Foundation be wary of any other one with Wish in its title.

              Those who run the lotteries love it when players look for consistency in something that's designed not to have any. So many systems, so many theories, so few jackpot winners. 

              Lep

              There is one and only one 'proven' system, and that is to book the action. No matter the game, let the players pick their own losers.

                grwurston's avatar - Lottery-012.jpg
                Win Today.
                bel air maryland
                United States
                Member #90247
                April 24, 2010
                8240 Posts
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                Posted: July 16, 2019, 12:41 am - IP Logged

                grwurston,

                Thanks for posting that list.

                I saw another one (maybe from www.charitywatch.org) that said the Make A Wish Foundation is real, but a lot of bogus charities try to play on that name and except for Make A Wish Foundation be wary of any other one with Wish in its title.

                You're welcome Coin Toss.

                You are exactly right. Most of them on the list do just that.

                Keep in mind this is only the 50 worst. Every time there is a disaster, hurricane, flood, etc, the scam charities come out of the wood work, trying to take advantage of someone else's tragedy by using others generosity to line their pockets.  It's just a sad situation. Sad

                "You can observe a lot just by watching." Yogi Berra, Hall of Fame baseball player.

                The numbers will tell you what numbers to play. Pay attention to the numbers.

                Every lottery system can be improved. If you're not winning almost every day, yours can be made better.

                  reddog's avatar - patch
                  Army Veteran
                  Durham, North Carolina
                  United States
                  Member #1616
                  June 5, 2003
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                  Posted: July 16, 2019, 6:57 am - IP Logged

                  I used to do this years ago. I, too, had the software that auto-filled your entries and then the sweepstakes got smart about that and made it where you HAD to manually fill in the blanks. I am not a ROBOT.

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                    100
                    ohio
                    United States
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                    June 11, 2004
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                    Posted: July 16, 2019, 12:40 pm - IP Logged

                    nikki cute

                     

                    everything i tried in the sweepstacks, i always lose,

                    went to a mall and put in for a new car sweepstakes, next thing i knew, i got a call talking about going to some seminar. went and wasted time. didnt get the car, since then, i stopped putting in at the mall

                      noise-gate's avatar - images q=tbn:ANd9GcR91HDs4UJhjxO7cmeMQWZ5lB_FOcMLOGicau4V74R45tDgPWrr
                      Chasing the Dream.
                      White Shores- California
                      United States
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                      December 12, 2012
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                      Posted: July 17, 2019, 1:18 am - IP Logged

                      You're welcome Coin Toss.

                      You are exactly right. Most of them on the list do just that.

                      Keep in mind this is only the 50 worst. Every time there is a disaster, hurricane, flood, etc, the scam charities come out of the wood work, trying to take advantage of someone else's tragedy by using others generosity to line their pockets.  It's just a sad situation. Sad

                      Thanks for the heads up G. I got a call a few years ago from an outlet out here calling for donations for the Solidarity for Police & Highway Patrolmen & Women. It was a mouthful then & still is now.

                      Funny thing is, l had just been watching Iron Man and recalled Stark asking agent Colson what S.H.I.EL.D stood for, since he was confused by the length of this agency's name. I told this outfit l would get back to them- they never called again. 

                       * Voice of Reason *   

                       

                      People who say it cannot be done should not interrupt those who are doing it- George Bernard Shaw.