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The Endless Work of Trying to Win Yourself a New Life

Inside the world of sweepers—committed competitors trying to game the system or maybe just win a lifetime supply of Gatorade.

Dave Taube has won a computer, a whitewater rafting trip, and several grills. There’s also the kayak, the powder-blue Coors Light onesie, and the Bruce Springsteen tickets. He recently took home $10,000 from Cost Plus World Market in its “World of Joy” sweepstakes. Recently, he found himself in the running for a trip to Antarctica, which would be the thirty-sixth vacation he’s won. His photo and caption, submitted in response to the prompt, “Tell us what you miss about international travel,” got enough votes to make the top 20. Next, the entries went to judging. In Taube’s photo, he’s slung with cameras and wearing safari duds, half-smiling, with a silver goatee. Strategically, he submitted his caption as a poem to make his entry distinct. 

I miss the thrill of booking flights, traveling far and climbing heights. I miss the joy of photo taking, exotic foods and memory making. COVID made my life unravel, now I really need to travel. So for some fun and elation, Antarctica’s my destination!

Taube, who is 65 and a decades-long resident of the Pacific Northwest, is a sweeper, a term that distinguishes the committed competitor from the casual, onetime entrant. Each day, he enters about 60 sweepstakes—which are random draws—and contests—which are judged. Sponsors range from his local pizza place to national corporations like Nordstrom. Taube dials radio stations to be the 102nd caller, and texts daily keywords like football and BBQ. He enters his contact information into online forms. He posts entries on Facebook and Instagram, then solicits the votes necessary to win by direct messaging allies—a collection of other sweepers who trade favors. 

Once, for a Cheez-It contest, Taube submitted a wine-and-Cheez-It pairing: Rosé with white cheddar. (His winnings: wine and Cheez-Its.) Years ago, he entered a contest for “the most boring person in the Pacific Northwest.” He won a whitewater rafting trip, a plane ride, and a certificate for a tandem parachute jump. He sold the certificate. 

Taube wins a lot. Each year, he comes out on top in—he estimates—70 to 100 competitions. Of those, perhaps three to five are worth $1,000 or more. He doesn’t have a traditional full-time job, and hasn’t since 1990. 

The winning takes time—about two hours a day for Carolyn Wilman, the “Contest Queen.”  When Coca Cola or Canada Dry run sweepstakes, Wilman “gets her butt outside” before the recycling trucks come, wearing rubber gloves and scouring her neighborhood’s bins. She unscrews the tops of bottles, looking for “instant win” codes. “You’ll write this article,” she told me, “and a lot of people will come to my website. They get all enthused, and then they realize how much work it is.” 

Wilman says sweeping changed her life, and now she’s an eager evangelist. Search her name and you’ll find her likeness everywhere—on books, her podcast appearances, her interviews on websites with names like “Super Lucky”—curly hair cut short, often pictured in bold glasses and funky jewelry, beaming in every photo. Her first prize, won in 1990, was a pair of tickets to an ice show. (The man she took with her became her husband.) Today, eight cases of Gatorade sit in Wilman’s basement in Ontario, Canada, the remnants of a year’s supply. “You can win things you can’t afford,” she said, “or replace things you already spend money on”: shampoo, potato chips, or in her case, beverages. “I don’t want to buy drinks. Right? Because we have drinks,” she said matter-of-factly. You can also win certain experiences that “money can’t buy”:  Wilman has met Sting and Michael Bublé. 

This is part of the allure: What sweeping offers, to an astounding degree, is a certain kind of lifestyle enhancement, the opportunity for winners to eat meals, take trips, see games, meet celebrities, and enjoy luxuries they otherwise aren’t able to access. It gives them the dignity of the extravagant. The motto of one sweeping website, Sweeties, is literally “Win what you can’t afford!” 

As in most plots to achieve the American dream, there are rules. In her book How to Win Cash, Cars, Trips and More!, Wilman tells you how to hit. There are lots of opportunities out there, so it’s best to narrow the field by setting goals. If you want a new washer-dryer set, enter for Best Buy gift cards, not shampoo. Always read the official rules, which are, in fact, legal texts. Know the eligibility requirements (some sweeps are only open to residents of certain states) and how many times you can enter (daily, weekly, only one time). Open up an email address just for entering. Make use of your online bookmarks. And like any good quasi-prosperity gospel, a sweeper has to get her mind right. The Contest Queen champions chakras and self-talk, karma and good energy. A better life is possible—with the right attitude. “Do you expect to win?” she asks her readers. “I do.” 

The world of sweepers can feel small. A 2011 estimate calculated that 55 million people in the United States enter annually, but only a fraction of those are putting in the same hours as someone like Taube. On the internet, they scour aggregator websites, sharing leads and celebrating wins. They use directories like Sweepstakes Advantage, which has almost 60,000 followers on Facebook. They subscribe to long-running newsletters like SweepSheet, which has boasted as many as 12,000 members, and more boutique offerings like Tom Cavalli’s website iWinContests (a “community of Sweepers and Winners”). “Fifteen to 20 percent of our members wish that I would double the [subscription] price tomorrow,” Cavalli boasted to me, because they would rather “pay twice as much but have half as many people” with the same insider knowledge. The Annual National Sweepstakes Convention can draw more than hundreds. This year, it’s in Scottsdale. Of course, they’re giving away prizes. 

Corporate contests fully emerged in the 1950s and ’60s, used by Madison Avenue marketers to source slogans while also selling products like toothpaste and tinfoil (every jingle or tagline submission required a proof of purchase). Contests rewarded not just wit, but other skills. Home cooks entered recipes to the Pillsbury Bake-Off; high-school musicians sang and played in Coca Cola’s Talentsville competition. Gradually, random-draw sweepstakes, presumably easier to run, increased in popularity (though creative contests still generate material for sponsors). The Publishers Clearing House sweepstakes was launched in 1967 to help sell magazine subscriptions. McDonald’s Monopoly started in 1987, incentivizing fast food purchases via game-piece collection (the game was later embroiled in an embezzlement scandal). 

Today, companies who run contests and sweepstakes wager that the value of “permission-based marketing”—addresses for mailers, emails for campaigns, social media accounts bloated with followers—will be well worth the cost of prizes over time, or the fee they pay a prize fulfillment company to run the sweepstakes for them. Eventually someone will buy something. Companies routinely make this bet: drink companies and snack companies and airlines and outdoor shops. Campbell’s soup and Jockey bras, VRBO and Tic Tacs and West Elm and Ford. “Four winners will get a leather sofa, a Sam Adams branded refrigerator, and a Pop-a-Shot basketball arcade game.” “Enter for a chance to win baby formula for a year! $1,200 prize value!” These prizes can look like magnanimity. For the sponsors, they’re often meager. Right now, Sour Patch Kids is giving away $50,000 cash: a transformational prize for many consumers but pocket change for the candy brand’s owner, Mondelez International, which in 2019 brought in $25.87 billion.

For serious sweepers, the hobby can be gig work. This isn’t true for everyone—some people are retired, or don’t need the money—but sweeping seems to attract those who find themselves outside of the traditional labor market, people for whom a little extra cash wouldn’t hurt. Some sweep single-mindedly, looking for electronics and cars they can resell, or gift cards they can spend. Wilman started sweeping in between marketing jobs after the dot-com bust: “It gave me something to do … because I was tired” of sending out résumés. 

Her book includes some miraculous testimonies of people who were similarly down on their luck. Wendy was on disability, and her husband was out of work. When they won a new home, they’d just signed remortgage papers to pay off their debts. “This is my biggest win so far,” she wrote. “Like the words in Elton John’s song, SOMEONE SAVED MY LIFE TONIGHT.” Carmen’s husband was also out of work; her part-time jobs weren’t bringing in enough, and everything in their home was in need of repair. On Christmas Eve, she slipped a batch of cookies into the oven and found the door wouldn’t close. She despaired: another broken appliance. Two minutes later, the story goes, a UPS truck pulled up. She’d won a $14,000 shopping spree at Sears, plus money to pay the taxes.

The Sears win is big—but some sweepstakes go even further, explicitly offering a whole new life. Not unlike the lotto—“Hey, you never know”—they draw on a certain kind of desire. The HGTV Dream Home contest, now in its twenty-fourth year, capitalizes on fantasy: What kind of parties would you throw if you had this kitchen? (The high can be short lived: Most HGTV Dream Home winners either take the cash alternative or sell their home back to the developer within a year of winning, unable to shoulder the tax burden.) 

Much of this focus begins to feel intentional. Anecdotally, sweepers are more likely to be women, and more likely to be older (though some online options try to draw a younger crowd—there are sweeps and contests on Instagram, even TikTok). Some live on Social Security, or disability. Even small winnings save money over time. Tom Cavalli said he hasn’t had to pay his cable or cell phone bills in six years because he wins so many Visa, Mastercard, and American Express gift cards. Those savings can add up. 

Stay-at-home moms are a recognized sweeper demographic. Wilman “used to breastfeed in front of the computer … click, click, click. I’d enter lots of toy contests.” Lauren, another sweeper, won a birthday package at a local play palace that saved her family from having to pay for a party. A gift card to Little Tikes bought toys for her church and a race car bed for her son. Taco Bell sweeps resulted in an Xbox and two PlayStations. “This hobby has been a huge blessing for my family,” she says. Every little bit helps for Cindy, a high school journalism teacher in Texas. “With two kids in college, any gift card is like winning the lottery.” Some websites (like Contests for Moms and Freebies 4 Mom) take advantage of this crossover and market accordingly, listing contests alongside recipes, craft ideas, and other hacks. 

Some sweepers target cash prizes over material goods: They were laid off, or need student loan payments, or even financing for film projects. One sweeper lost out on a $10,000 prize because she was on vacation, and didn’t respond in time. “The ironic part is two days before we left for our vacation, my husband got into an accident with our car and it was totaled,” she wrote. They had no collision insurance. “The prize would have paid for a car with no payments.” 

But as Wilman puts it: “You don’t win mortgage payments.” You win a year’s supply of Lay’s potato chips. You win a sweatshirt. Sweeping can’t supplant a regular paycheck, health insurance, or paid leave. Like any side hustle, it promises flexible, supplemental money—but it requires time, and the payoffs are unreliable.

It’s also easy to get discouraged. There’s a lot of losing, a lot of small perks and life-changing wins that seem to slip through one’s fingers. On the iWIN Facebook page, Cavalli advertised a class (“30 Things to Make Sweeper Life Easier”) and offered to give away a few admissions for free. The comments filled with need. “I’d be happier and other areas of my life would benefit from me becoming a more efficient sweeper. I want to win, win, win, I just want to stop giving up sleep to do so,” wrote one woman. “I need to make my sweeping life easier because it’s starting to impact my other life!” wrote another. The women bemoan their computer illiteracy, their disorganization, their mistakes, their wasted time. 

That wasted time still translates to clicks, data, shares. It still pays off—just not for the sweeper. Realtime Media, a full-service digital promotions company, touts case studies of the sweepstakes it’s helped sponsors run. Royal Caribbean collected consumer data via a “fun profiling quiz”; 35 percent of users booked a cruise after taking it. Maybelline gathered over 100,000 registrations for a makeup giveaway. Hershey got more than 800,000 registrations, plus a 22 percent social share rate, by giving away treats.

Nevertheless, the sweepers persist. Perhaps they can squeeze something for themselves out of those corporate marketing budgets. Perhaps they’ll be the lucky ones. Their sacrifices—time, attention, data—are costly, and yet they make them still, hoping that a little bit of capitalism’s excess will fall into their laps. 

Sometimes, they’re successful. Take Dave Taube. He’s no victim—he’s victorious. His poem won that trip to Antarctica. He’s going to see whales, seals, and penguins; he’s going to kayak between icebergs. He also recently won an air fryer. He sent it to the sweeper who tipped him off about the Antarctica opportunity. “I enjoy helping people who help me,” he said. “It’s a win-win situation.”