The women who win hundreds of sweepstakes per year Winning online sweepstakes is supposedly an act – The Hustle

Click here to win a free trip to Iceland! … Enter to win a 2019 Ford F-150! … Share a photo on Twitter and win a lifetime supply of Hershey’s Kisses!

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.

A sweepstakes advertisement from a 1962 issue of Argosy Magazine (Photo: Joe Haupt, via Flickr)

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.

Most sweepers win multiple prizes every year (The Hustle)

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.

Coke flanked by a selection of recent wins (via Ms. Coke, SuperLucky.me)

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.

Top: Carolyn Wilman (tan sweater) at a meet-and-greet with Sting that she won; Bottom: Wilman literally enjoying the fruits of her labor (via Ms. Wilman)

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.

Brands almost always get more out of a promotion than they put in (The Hustle)

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 aggregates 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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