Winning in a Digital Era: The World of Online Sweepstakes

Make Money Onlineby Mashum Mollah18 November 2020

Online Sweepstakes

In The Color of Money, hustler Fast Eddie Nelson (played by the incomparable Paul Newman) famously said that money won is twice as sweet as money earned. Eddie Nelson would probably agree that applies to colonoscopies won as well.

Pick the right online sweepstakes and you could win money, cars, a year’s supply of string cheese, or, yes, even a colonoscopy.

But you’ll need the right strategy. With the rise of online giveaways, the competition for that string cheese has only gotten more cutthroat. In the analog days, hardcore “sweepers” might spend hours on envelopes and travel to different zip codes to mail them. Now, that effort has gone digital, and the field has only gotten deeper.

So more and more contestants are trying — and some are cheating — to win. But do your homework and you might just get the edge you need to compete.

Why Do Companies Hold These Contests?

Before we get into how you can win them, you might be wondering why companies hold these contests in the first place. The answer, perhaps obviously, is marketing: When people talk about the contest, they talk about the company.

More specifically, the real marketing power of sweepstakes comes from earned media. Simply put, earned media is when you get other people to publish content about your company without paying them for it.

Come up with a big enough or interesting enough sweepstakes, and media outlets will talk about it. Essentially, contests create free advertising.

How Much Can You Really Win?

For most people, entering sweepstakes is a one-time lark or, at best, a gamble. But, in the same way, that a dedicated pro can use card-counting to bend the odds of blackjack in their favor, dedicated sweepers can turn winning sweepstakes into a science.

Di Coke, a serious sweeper, and winner of over $300,000 in prizes took an informal poll of the readers of her sweepstakes blog. Of the 585 respondents, about half reported winning at least $1,250 a year in prizes. A quarter reported winning more than $3,000 a year.

So it’s possible to win big. But you need to know what you’re doing. Serious sweepers might spend an hour or two a day entering contests, but in that time they may send in as many as 36,000 entries a year.

How do they do it?

Finding the Right Online Sweepstakes

The first step to maximizing your winnings is picking the right contest to enter. The problem is, there are thousands to choose from online. No person could sift through all of that alone.

Fortunately, online directories will compile the most recent contests to help you find the right ones. You can choose online giveaways by the number of entries allowed or by the company running the contest if you want to find Amazon giveaways or something else specific in nature.

Once you have your list, you want to narrow it down to the contests that you’ll have the best chance of winning. At The Balance Everyday, Sandra Grauschopf explains how to pick contests that maximize your chance of winning. She suggests you look for contests that:

  • Have the fewest competing entries (generally contests with entry restrictions, niche prizes, or cumbersome entry rules)
  • Allow you to enter more often (although then you could be competing with bots, as discussed below)
  • Offer more prizes

Contests with better prizes may be more exciting to win, but the odds are likewise lower.

Watch Out for Bots and Scams

Like Twitter, some sweepstakes and contests online are crawling with bots or automated accounts that send in thousands of entries. In Summer 2020, a T-Mobile contest was upended when nearly a third of the winners all came from the same small Pennsylvania town. Turns out, one hacker there had used bot accounts to submit countless entries. No human could compete with that.

Even more nefarious, online scammers use fake contests as a way to trick people out of their money. In this modern twist on the classic “Nigerian prince” scam, scammers tell you that you’ve won a fabulous contest, but you need to pay a fee before they can deliver the prize. Such requests are an immediate sign of a sweepstakes scam, especially when the messages are full of typos or ask for your banking information.

Stick with reputable contests, and always record which ones you’ve entered, and you can avoid these obvious scams.

Make Automation Work for You (Or Avoid It Altogether)

Without coding your own bots, you won’t be able to win against the fully automated competition. Fortunately, most contest rules exclude such cheating. But the rules still allow you to use certain automated tools to make things easier for yourself.

We’ve already discussed online directories. Automated form fillers are another great tool to make you more efficient. Form fillers are software that can fill in entry forms instantly, saving you the trouble of doing it yourself each time. You store the information you need, and you can enter it with a single click.

Beyond cutting the time it takes to enter, these form fillers also eliminate typos. There’s no sense in winning if the prize goes to someone else’s address.

But, the easier a contest is to enter, the more competition you will have. So, it might be worth prioritizing contests that ask contestants to submit something like a tweet or photo. These entries can’t be automated.

That’s how Di Coke amassed her big winnings. It takes more effort, but it lets you stand out — and, as an added bonus, it keeps out the bots.

Now Start Winning!

As Fast Eddie said, there is something undeniably sweet about winning, including online sweepstakes. From picking the right contests to streamlining your entries, you now have the tools and knowledge you need to compete with the sharks, the real sweepers.

How much time you want to devote to entering sweepstakes is up to you. But you can’t win if you don’t play, and you can’t win much if you don’t play smart.

And if, once you see your new winnings, sweeping still isn’t for you, check out some of our other posts to find your next life upgrade.

Read Also:

Mashum Mollah

Mashum Mollah is an entrepreneur, founder and CEO at Viacon, a digital marketing agency that drive visibility, engagement, and proven results. He blogs at

View All Post

Leave a Reply

Your email address will not be published. Required fields are marked *

You May Also Like