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Meet The Community That Always Seem To Win Online Sweepstakes (thehustle.co) 128

The Hustle profiles a community for whom entering online sweepstakes are a way of life. And 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..."

"Winning online sweepstakes is supposedly an act of pure luck -- but some contestants claim to have it down to a science." 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...

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

- She creates a new email specifically for sweepstakes.

- She uses sweepstake aggregators (resources that list thousands of legitimate promotions in one location) to find form-based competitions.

- 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 member of the "sweeper" community brags that they don't engage in highly risky behavior -- "But with sweepstakes, I can pretty much guarantee I'll win."
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Meet The Community That Always Seem To Win Online Sweepstakes

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  • by Antique Geekmeister ( 740220 ) on Monday July 08, 2019 @02:38AM (#58888926)

    Robert Heinlein described precisely this process in 1961, in his award-winning children's book "Have Space Suit, Will Travel". The book was treasured by me: it described a wonderful working relationship with the hero's parents, and the lifesaving benefits of doing _all_ the work possible with what tools you have.

    • Re: (Score:2, Interesting)

      by Anonymous Coward

      Robert Heinlein described precisely this process in 1961, in his award-winning children's book "Have Space Suit, Will Travel". The book was treasured by me: it described a wonderful working relationship with the hero's parents, and the lifesaving benefits of doing _all_ the work possible with what tools you have.

      I remember certain families in my town being in the habit of this at the local grocery store back in the 80s. Four people, mother and three kids, standing at the table next to the a raffle box at the supermarket, filling out the entire stack of forms and stuffing them into the box by the dozens. You can call it resourcefulness, you can call it survival of the fittest by "doing _all_ the work possible with what tools you have", to me it just seemed pathetic, miserly and just generally not worth the low opini

      • to me it just seemed pathetic, miserly and just generally not worth the low opinion of you

        Imagine how low their opinion of you must have been, lazy and ignorant as to the keys of success as you were...

        When you stop caring what other people think of you it gives you amazing powers of success. I think it's called herd immunity...

    • by Anonymous Coward

      Heinlein would be rather pissed off to see the book described as a "children's book". That was certainly not his intended audience.

      • by Anonymous Coward

        Yes it was his intended audience. Have Spacesuit, Will Travel is a young adult novel written for new readers of novel-length books. It is part of a collection called âoeHeinlein Juvenilesâ and is indeed an excellent book.

    • Your comment seems aimed at the post yesterday about a lot of the work for the Apollo missions being done by hand, not this one about sweepstakes.

      Are you sure you commented on the right post?

    • by thomst ( 1640045 )

      Antique Geekmeister noted:

      Robert Heinlein described precisely this process in 1961, in his award-winning children's book "Have Space Suit, Will Travel". The book was treasured by me: it described a wonderful working relationship with the hero's parents, and the lifesaving benefits of doing _all_ the work possible with what tools you have.

      I disagree withg your characterization of Have Spacesuit, Will Travel as a children's book. It's not. In the publishing industry, the marketplace for what you're calling "children's" literature is segmented by age. In current jargon, Spacesuit is categorized as a Young Adult novel - which is to say it's targeted at readers aged 12-18, like all fiction in the YA market category. Children's Literature is a completely seperate and very different market.

      In 1958, when Spacesuit was firs

  • by Anonymous Coward on Monday July 08, 2019 @03:59AM (#58889046)

    Her persistence has paid off. In her best month, she won 83 prizes; in her best year, earnings topped $60k.

    This says it all really. If you spend all your time slaving away in form-entry hell, you might earn enough to get by on a salary similar to an admin assistant, meanwhile contributing nothing to society and producing nothing for posterity.

    • by AmiMoJo ( 196126 )

      With browser auto-fill it's not much of a burden. Just go to the aggregator sites and browse a few forums where the competitions get reported, and it's a couple of clicks to enter.

      The bigger burden is sifting through the mountain of spam you get every day, looking for messages about your winnings.

  • Some lotteries have withheld winnings because the "winner" was believed to be laundering money Someone with illicit cash persuades the real winner to sell their ticket,

    • by jrumney ( 197329 ) on Monday July 08, 2019 @05:44AM (#58889208)
      These aren't real lotteries though, they offer non-cash prizes like holidays, so not particularly useful for money laundering, and the price of entry is your soul presented to marketers on a platter. These people are merely gaming the system by superficially giving the marketers the personal info they want, while withholding probably the most valuable part - their eyeballs on all the disguised advertising in the competition entry form.
  • by chthon ( 580889 ) on Monday July 08, 2019 @04:16AM (#58889074) Journal

    And that already since the eighties.

    He is a teacher, and his hobby was the same: find out where prizes could be won, and then find out how to increase your chances.

    E.g. he looked out for large stocks of things at lower prices.

    You must be able to invest something, but long term, you can get it back. The guy even won a complete new house in the course of time.

    But like all such things, it must be a hobby: you have to like to do the work for it, or be able to put up with the work, because you know that you will win. In other words, you must be treasure hunter in heart and soul.

    • Re: (Score:3, Informative)

      by AmiMoJo ( 196126 )

      People in the UK have been doing it for decades too. There is a community over on the Money Saving Expert forums.

      The main issue, aside from the will to put the time in, is that your name, address and phone number ends up in thousands of marketing databases. Your house gets flooded with spam, let alone your inbox. Obviously you can do things to limit the damage, like having a dedicated spam email address and spare SIM card, but you still have to check them periodically to see if you have won. And you can't r

      • by tlhIngan ( 30335 )

        The main issue, aside from the will to put the time in, is that your name, address and phone number ends up in thousands of marketing databases. Your house gets flooded with spam, let alone your inbox. Obviously you can do things to limit the damage, like having a dedicated spam email address and spare SIM card, but you still have to check them periodically to see if you have won. And you can't really lie about your name and address because it would invalidate many of your winnings.

        It sort of depends how fa

    • You must be able to invest something, but long term, you can get it back.

      My grandmother had a system that only required mailing a complaint, such as "Some of the OREO's didnt have filling" and sure enough she would get coupons in the mail for free stuff.

      • by dcw3 ( 649211 )

        My mom used to do this with things like TV dinners, where you'd see a decent looking meal on the cover, and open it to see shriveled peas and such. A letter to the company usually got us coupons for free items. Mom had time for this kind of stuff though...she was a grocery cashier for many years, and couponer (we had boxes of coupons at home).

  • by Anonymous Coward

    So some of the techniques described violate most sweepstakes rules, namely:

    AUTO form-filling--many rules ban bots or other forms of automation

    MULTIPLE e-mail addresses for one PERSON or HOUSEHOLD

    Now if some sweepstakes do NOT include these rules, fine, go ahead and create multiple email addresses. Go ahead and automate.

  • My mom entered mail in sweeps when she sent a letter or post cards I had a chance to buy a Dodge Charger Rose won but could not afford it then. . She and her friend Rose would go to the PO to mail twenty entries every day. Rosie was sneaky, she was sending forty every day, hid it from my mom. Rose won a 1960 Charger. With the Hemi.
  • by SirDrinksAlot ( 226001 ) on Monday July 08, 2019 @05:29AM (#58889180) Journal
    I once worked for a SCCA Pro racing team as a pit monkey for a weekend. The team some time before had a sweepstakes to send two people to the Toronto Grand Prix fom the United States and someone who does this activity of throw shit at the wall and see what sticks won. This person who won it was some single mom with a toddler, neither of them gave any shit about what they were doing there and screwed off as soon as the paddock tour was over, I assume they tried to sell their sweet tickets for the rest of the weekend. I didn't see them again even though we were supposed to.

    I guess if you're a single mom and you can't afford to do things like vacations for your kids then this is kinda cool way to expand their world but in this case the kid was in a stroller and wouldn't remember sitting in a race car 5 minutes later.

    The contest was intended for fans of the team and this outcome really disappointed one of the drivers. This is when I found out about "contest winners" because it's usually a contest winner not a fan that wins these prizes they have. So ultimately in this case, the contest winner took something away from the intended audience and it wasn't even something they appeared to enjoy.
    • Badly designed contests are badly designed, film at eleven.

      If the goal is to have a fan win the contest, then you design the contest such that only a fan can win. Present the contest at an event attended by fans, for example.

      • I was thinking exactly this as I was reading the GP's post. The article notes that these people are using auto-fill forms to enter as many as possible in as little time as possible. To weed out these folks you just need to throw in a little bit of overhead which any fan would be happy to engage in, but which the form-army wouldn't.

        * Provide a drawing of your favorite racer
        * Best topical haiku wins (randomly select a half-dozen winners, pick the best one.)
        * To prove you're a fan, what's X's favorite Y?

        If you

  • by Anonymous Coward

    Let's see her auto fill the PCH forms. Their website is a designed maze of flashing lights, weird links and data entry. You never really know whether you're entering the sweepstakes or selling your kidneys.

  • Fraud? (Score:4, Insightful)

    by fluffernutter ( 1411889 ) on Monday July 08, 2019 @07:46AM (#58889544)
    This person is only successful doing this because to most other people it feels like fraud.

    Congratulations to those people who live between the lines of what is 'legal' and what is 'allowed'. Some of us can't live with ourselves if we behave this way.
    • Re:Fraud? (Score:5, Interesting)

      by mark-t ( 151149 ) <markt@ner[ ]at.com ['dfl' in gap]> on Monday July 08, 2019 @08:07AM (#58889608) Journal
      That's because if you read the boilerplate that is part of the rules for most sweepstakes, it will say something not entirely unlike this:

      The use of any automated launching or entry software or any other mechanical or electronic means that permits the participant to automatically register and/or enter repeatedly is prohibited and all such entries will be disqualified.

      So, while perhaps not exactly fraud in a legal sense, definitely a violation of the rules

      But I expect that the person probably holds the perception that there's nothing wrong with breaking rules as long as you don't get caught, especially since the consequence for breaking the rules even if you do get caught is no worse than if you hadn't entered in the first place.

      • But I expect that the person probably holds the perception that there's nothing wrong with breaking rules as long as you don't get caught, especially since the consequence for breaking the rules even if you do get caught is no worse than if you hadn't entered in the first place.

        That's the kind of thinking that leads to all kinds of crime.

      • Why do we constantly praise people for having relaxed morals? This person has gotten ahead by literally ignoring the instincts within them that has made human society successful until now. Is that a good thing?
        • It's what made our ruling class successful. People won't copy anything that's not successful. Brian Epstein was a friend to Bill Clinton and gave rides to him on his private jet, nicknamed the "Lolita Express". With role models like this, who can blame them for doing what works?
        • > This person has gotten ahead by literally ignoring the instincts within them that has made human society successful until now. Is that a good thing?

          I think you'll find that "greed" is an instinct for humans, both a biological instinct and a strongly reinforced social behavior. Since the harnessing of greed can produce extraordinary productive behavior, it has proven to be a good thing on many occasions.

          • Greed didn't allow us to build and keep society working. Society works in spite of it. In fact, greed has been the end of many societies. It's the other people who bring things back together again.
            • > Greed didn't allow us to build and keep society working.

              Not only gread, certainly. But greed provides _incentive_ to produce, to trade, and to achieve in the hope of rewards.

              > Society works in spite of it. In fact, greed has been the end of many societies.

              As has money, water, and technological change.

      • That's because if you read the boilerplate that is part of the rules for most sweepstakes, it will say something not entirely unlike this:

        The use of any automated launching or entry software or any other mechanical or electronic means that permits the participant to automatically register and/or enter repeatedly is prohibited and all such entries will be disqualified.

        Usually, these rules are written to avoid one single participant to fil 50% of all submitted forms to a sweepstakes and thus increase their chance (metaphorially, if every second form in the urn is their, they have a very high chance of winning). That's what would be considered cheating.

        If you read the summary, that's NOT what she's actually doing. She's submitting exactly one single form, not repeatedly. She's taking exactly the same chance as any other participant, per sweepstake.Only, she's participating

        • by mark-t ( 151149 )
          Reread what I wrote....

          ...permits the participant to automatically register and/or enter repeatedly...

          In other words, manual entry into the sweepstakes is required. You cannot have software do it for you.

          You can at best use something like form autofill to fill in the blank fields on a sweepstakes form, but the sweepstakes must still be entered *manually*.

          So, uhmmm.... yeah. Cheating.

          The only reason she's won prizes is because she didn't get caught.

          • In other words, manual entry into the sweepstakes is required. You cannot have software do it for you.

            If the sweepstakes has a web form or email entry system, then you are already using an automated system and software to enter. Any prohibition on the use of software for such a sweepstakes is patently absurd.

            The only reason she's won prizes is because she didn't get caught.

            She's won prizes because she enters a lot of sweepstakes.

            • by mark-t ( 151149 )

              She's won prizes because she enters a lot of sweepstakes.

              Obviously, but if any of them ever catch on to how she's doing it, she will stop winning.

              Any prohibition on the use of software for such a sweepstakes is patently absurd.

              If you are only entering them as fast as you can humanbly enter them, obviously there's no problem.

              If you are entering 200 different sweepstakes in one hour with only a few clicks, then the process of actually entering each sweeapstakes has been clearly automated.

              But hey, if you t

              • by DRJlaw ( 946416 )

                But hey, if you think there's nothing wrong with it and you are called to win a prize, go ahead and openly tell them how you won it before you collect it, and see if they still want to award it to you....

                You appear to have this odd idea that the holder *cares* how you provided your entry information to the contest in order to win it. As if the entry information itself was not a benefit that the contest holder was seeking. As if the holder is simply charitably giving away the prize and destroying the info

              • Obviously, but if any of them ever catch on to how she's doing it, she will stop winning.

                In a 400-participant sweepstake, every one has a 0.25% chance of winning.

                TFA's sweepstakes addict still has 0.25% chance of winning, just like anybody else.
                It' doesn't matter if she's literally putting a paper form in a physical urn,
                clicking on webform using her Firefox browser software
                or using a python script she wrote.

                She's still using up exactly 1 of the 400 slots, just like the 399 other participants, she's not twisting the odds, she has the exact same chance of winning just like anybody else.

                She only s

          • by DRJlaw ( 946416 )

            Reread what I wrote....

            ...permits the participant to automatically register and/or enter repeatedly...

            Reread what you wrote. Automatically registering and/or entering just once does not violate that rule.

            So where are you getting "repeatedly" from? Improperly aggregating different sweepstakes under one instance of sweepstakes rules?

            • by mark-t ( 151149 )

              Let me illustrate with parentheses:

              ...(automatically register) and/or (enter repeatedly)...

              To enter 200 sweepstakes with only a few clicks, there *HAS* to be some automation happening.

              I'd be willing to bet that if a person used this technique to win a sweepstakes and they said what they did before actually claiming a prize, if the company didn't disqualify them right there, they'd probably still be banned from entering future sweepstakes.

              And when you are pretty sure you can't be open and up front a

              • by DRJlaw ( 946416 )

                Let me illustrate with parentheses: ...(automatically register) and/or (enter repeatedly)...

                That would be one construction. Let me counter illustrate:

                ((automatically (register and/or enter)) repeatedly)

                Which is equally valid because the grammar is ambiguous.
                "And/or" may function -- however poorly [www.slaw.ca] -- as a compound verb [yourdictionary.com] modified by both adverbs.

                To enter 200 sweepstakes with only a few clicks, there *HAS* to be some automation happening.

                To enter 1 sweepstake with any clicks means that there *HAS* to b

                • by mark-t ( 151149 )

                  Seems pretty open and up front to me. What's been concealed, exactly?

                  She's already won, and raked in the prizes, and I doubt the sweepstakes runners are paying attention. Color me surprised if they express having no problem with her automatic entering into hundreds of sweepstakes every day with just a few clicks of a mouse *before* she's collected her winnings.

                  I'd be willing to be that they'd not be, if only because sweepstakes are regulated by laws that, for example, require that they be open to all le

                  • by DRJlaw ( 946416 )

                    I'm pretty sure one could still be disqualified for cheating.

                    No, you're not pretty sure. You're asserting a fact-free gut feeling that a sweepstakes holder can disqualify someone from future sweepstakes. But state sweepstakes law requires that sweepstakes be open-entry based upon generally applicable criteria that are typically limited to age and residence.

                    Don't be "pretty sure." Prove it.

                  • I'm pretty sure one could still be disqualified for cheating.

                    Cheating is usually about artificially twisting the chance of winning.

                    That would be the case when using automation to repeatedly enter/register a sweepstake.

                    Which is not what she did.

                    No automatic repetition was involved, she got the same chance as everyone else.

                    Yes, somebody could twist the wording of the ruling to mean simply "software automation" (with omitting of the repetition part due to ambiguous grammar), but that would also exclude anyone who applied online using a web browser. And at the same time

  • Another person with relaxed morals makes money in America, news at 11.
  • "Couponing as a way of life" has been around longer than I've been alive.

    Even before online shopping there were people who "earned" enough by using coupons and mail-in refunds than their grocery bill for the year was essentially paid for. If you are talking a $400/week that's almost $5000/year in today's dollars.

    Of course in the pre-internet days it took a lot more time and effort.

  • Do you want to quit your day job and just rake in sweepstakes money for a living? If you said yes then for a limited time only you can be one of the lucky few to read my book for a special price of $99.99 right now!!! I will teach you the algorithms and software used to bank you $6k a month at least. Why wait to be rich! ORDER NOW!!! ....
  • Sure, create many emails for many contests, but what about all the other data like postal & phone?

    $60k at the top end is not worth the junk snail mail and barrage of phone calls, even to the burner phone.

    And then you have some personal info on many thousands of marketing lists, sure with fake birthdays and other data, but how many bank accounts are eventually opened in your name?

  • I sounds like they're doing a full-time data entry job and earning more or less what a full-time data entry job would pay.

    If they enjoy doing that, I suppose there's no reason they can't, though if I was entering data in a website as a job I'd personally rather it was something useful helping customers or medical research or anything that's benefiting society one way or another.

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