Meet The Community That Always Seem To Win Online Sweepstakes

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.”