How to Win Online Sweepstakes and Contests

How to Win Online Sweepstakes and Contests

How would you like to open your email to find, “Congratulations! You just won our $10,000 sweepstakes!” Even so, most people avoid online sweepstakes because they think they can’t win or they think sweepstakes are all marketing scams. Well, I can tell you that not only can you win, but it is easy and fun. Be that as it may, there are strategies you must take to both win and not get scammed by unscrupulous marketing companies.

Over the years, I have won thousands of dollars in cash and prizes. Regardless, at one time, I was skeptical too. I had occasionally entered online sweepstakes here and there, but never won anything. This was until a friend told me he had just won a very large online sweepstakes. I picked his brain, started entering, and then started to see the results.

Examples of Online Sweepstakes Winnings

  • Coupons for free food items and candy
  • Free novelty and promotional items
  • Store gift cards for restaurants, gas stations, grocery stores, and online retailers
  • Vacations, hotel stays, frequent flyer miles, and car rentals,
  • Prizes like children’s toys, coffee makers, and gas grills, and
  • Cash (paid both by check and gift cards) from $5.00 to thousands.

Why Run Contents and Sweepstakes?

The primary purpose of giveaways is for self-promotion and marketing. However, for the most part, you should not fear about receiving a ton of junk email. When you enter, they will ask for your name, contact information, and sometimes demographics. But reputable companies will not send you promotional emails unless you opt-in to receive these updates. What they ultimately want from you is the goodwill and word-of-mouth marketing connected to online sweepstakes and contests.

The data shows 72 percent of all internet users, within the United States, are on Facebook. Also, the average Facebook user has roughly 190 online friends. Moreover, 684,478 pieces of content are shared on Facebook every minute. Therefore, companies endeavor to have you share information, even if it is sweepstakes information, about their brand, product, or service. All this activity builds awareness, loyalty, and demand.

How to Win Online Sweepstakes

While online sweepstakes are games of chance, they are not a form of gambling. When you go to a casino or play the lottery, there is no guarantee anyone is going to win. With gambling, the goal is to keep people from winning for as long as possible so that the casino or the government can make as much money as possible. With a sweepstake, there is an absolute winner, within a specific amount of time, and with a defined payout. Your chance of winning is merely a numbers game, controlled by the total number of entries. Nonetheless, someone will win. The below strategy will have you winning this game of numbers.

Find Online Sweepstakes – There are many ways to discover giveaways. You can search Google, Facebook, Twitter, and other social media sites and search engines. Regardless, the easiest way to find sweepstakes is with a site like Many of these sites will list only giveaways from reputable companies, limiting your exposure to marketing scams.

Choose the Best Sweepstakes – Personally, I recommend entering any and all legitimate sweepstakes. The more you enter, the more often you win. That said, there is a time commitment. Therefore, pick sweepstakes that you really want. For instance, all giveaways with a cash prize are a no-brainer. Also, remember you are responsible for paying taxes when you win. Winning a $50,000 new car is awesome. However, if you plan to keep it, paying the taxes can break your bank account.

Read and Follow the Rules – Contest rules are often difficult to read, but it is essential. The good news is many will use the same language. Once you have read a few, it becomes easier. Common rules include a limit on the number per household and a ban on software to complete entries. Another common rule includes a statement that winners are contacted by email, and you have x-number of days to respond before another winner is selected.

Be Organized – Sites like will have features to organize the sweepstakes you enter. If you don’t want to use these kinds of websites or enter giveaways not listed on these sites, use a spreadsheet to list and organize your entries. Important data includes contest name, sponsor name, URL, the top prize, entry frequency, deadline, and drawing date.

Be Consistent – As stated, winning is a numbers game. You have no reasonable chance of winning if you enter online sweepstakes and contests infrequently. As little as 15 minutes per day can start the process. Of course, the more time you invest, the more you will win. I have found an hour per day, in the evening when I’m watching television, is very effective.

Enter Frequently – Many online sweepstakes allow daily entries. However, the typical person is not going to take advantage of this. Remember, your odds of winning is based on the number of total entries versus your entries. Therefore, it is better to have 365 entries out of 10,000 than just 1 entry out of 10,000. Take advantage of daily, weekly, monthly, and unlimited entry offers.

Monitor Your Email – Some people create email accounts specifically for online sweepstakes. Some of this is the fear of spam, but it also helps keep you organized. Many companies will send winning notifications to your inbox. It is also not uncommon for prizes to come through email, such as virtual gift cards. You will have to check your email at least daily, and even scan through your spam folder. You don’t want to lose out on a winning notification.

Properly Claim Your Prize – Small ticket items tend to be easy. You will likely receive an email, with a link to confirm your information. If it is a prize over $600, the company will likely have you sign and notarize a statement verifying your identity and making it possible to send you a 1099 for tax purposes. It is important to complete this within the required amount of time. Additionally, there may be other requirements, like using your name and likeness in promotional and marketing material.

Don’t Get Frustrated – Winning takes time. Expect not to see your first win for a few months, and consistent winning for a year. It takes time to build a portfolio. Sweepstakes are conducted over months. Don’t expect fast results. Regardless, once you start winning, it becomes rather consistent fairly quickly.

If you would like to talk about winning online sweepstakes, or have any questions, please add a comment below.

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