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How Entering Sweepstakes Changed My Life Forever

entering sweepstakes

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It all started with a duffel bag.

It was 2012, and I was a new stay at home mom. I was looking for a hobby to keep me busy while my husband was at work, our newborn daughter slept, and the apartment was eerily silent.

I figured it might be fun to try and see if I could search for some free samples; having little surprises arrive in the mail like that might be cool.

I started signing up for every freebie I could find and sure enough, soon I started getting packets of shampoo samples, candy, and other little goodies in the mail. It was exciting to get these treats; I never knew what would show up or when.

THEN- I found a site called Dailybreak.

Today, Dailybreak is more of an entertainment website, but years ago when I first discovered it, it was more focused on gaming and prizes. You could enter to win all sorts of neat things from clothing and accessories to gift cards and cash. The best part was that there was no purchase required to enter.

I was skeptical at first, because I had heard horror stories of people who had been scammed through sweepstakes, and obviously I didn’t want to go through any of that. I decided to give it a shot however, being that it was easy and fast to enter, and most of all, it was fun.

Then one day in October 2012, I received a message from Dailybreak.

I had WON one of their sweepstakes.

I’ll never forget it. The prize was a Puma duffel bag, very similar to this one:

entering sweepstakes

Okay so you’re probably thinking, woop de doo, what’s the big deal about a duffel bag?

While it’s definitely not the most valuable prize in terms of monetary value, that duffel bag changed everything. Once it arrived a couple weeks later in the mail, I realized that wow, yes- sweepstakes were real, real people win them, and MAYBE–I could win one again.

I kept entering, and a few weeks later my second win came in, also from Dailybreak. I’d won a pair of Ugg boots. Now, those Uggs were definitely worth more than the gym bag, and I was starting to get very encouraged. I realized that there had to be other sites that offered these types of sweepstakes.

Sure enough, after some more research I came across a site called Sweepstakes Advantage. They claimed to be the largest directory of free sweepstakes on the web, and had been established since 1997. I signed up, and started taking a look at their offerings.

And wow.

These sweepstakes? They were everywhere.


I mean, every brand under the sun seemed to be running a promotion at one time or another, with prizes as small as a keychain to as big as a car.

A whole car, y’all.

Why didn’t I notice this before?

I got very excited at the prospect of winning another amazing prize, but wasn’t sure how to begin. The Sweepstakes Advantage website included a forum of other members who enjoyed the hobby of entering these promotions on a regular basis. I joined, and was soon making friends and reading the stories of other “sweepers”.

Their stories seemed incredible; tales of winning huge cash prizes, luxury watches, cruises, all expense paid trips, and much more. These were real people from all over the country, young and old, single and married, working and retired. I started connecting with certain people through social media, as I soon learned that having a strong sweeper network can certainly help when it comes to winning.

The more I explored this new world, the more opportunities I found. As I kept entering sweepstakes, I started winning more, and so did my new group of friends. It was amazing. The community was so united; everyone rejoicing in each other’s success.

The wins started coming in more frequently. Some days I would even have 3-4 prize notifications. I remember one day in particular I actually won 8 different sweepstakes. From 2012 until now, I’ve racked up my fair share of amazing prizes. A few notables include:

-A $1,000 green amethyst ring from Sears

-A year’s worth of burgers from Red Robin

-An Xbox 360 console

-A $1,000 multimedia car system from Clarion

-$4,000 in Home Depot gift cards

-A $400 Vitamix blender

-A $500 jewelry shopping spree

-$500 cash (twice in 3 months)

-A $5,000 75″ Sony TV

-A $600 Wolf Gourmet blender

-A $600 Sleep Innovations mattress

-An $800 Bosch dishwasher

-A $2,000 diagnostic tool for cars (my husband LOVED this one!)

-A brand new Samsung Galaxy S8- before it was released

And this is just the tip of the iceberg. There have been thousands of dollars more worth of gift cards, cash, electronics, appliances, beauty items, clothing, food…just about anything you can think of. When I am consistently entering sweepstakes, I average around 200-250 individual wins per year, of all sizes. In 2016 alone, I won over $20,000 worth of cash and prizes.

The sky is the limit when it comes to this incredible hobby; I know people who have won even more than I have! I asked some of my closest sweeper friends to share some of their biggest and most favorite wins:

-In 2013, my friend Tonya A. won a sweepstakes hosted by Tyson foods. The prize was a trip to the 2014 Super Bowl. Because the she wouldn’t be able to enjoy the prize until the following year, they offered her a cash option of $12,600 instead. She’s also won 2 trips to Napa Valley, a trip to Chicago for the Lipton Chef Fest sweepstakes, a 55′ smart TV, a check for $2500, several $1000 gift cards, 2 years of Netflix, and a year of coffee and ice cream.

-My friend Kimberly M. has won an incredible $25,000, a trip to Sweden (she took the cash alternative of $7,500), all inclusive trips to a resort in Riviera Maya and to California for the National College Championship Game, a couple of $1500 cash prizes and a $3000 American Airlines voucher.

-Pamela M. told me about her amazing trips to Disney World and Puerto Vallarta, Mexico, as well her experiences seeing the Doobie Brothers in Las Vegas and her trip to the Austin music festival in Texas. Pam has also won a Kawasaki motorcycle that she ended up selling for $13,000, and $1,000 from Publisher’s Clearinghouse. With over 20 years experience in entering sweepstakes, she’s won more amazing prizes than would fit in this post!

-When I asked my friend Paula S. about her wins, she said some of her favorites were 70″ and 60″ TVs, a Big Green Egg, a trip to UFC cage fights in Las Vegas, and a trip to Florida for the Daytona races. There, she got to meet the drivers and hang out on pit row! Recently she won another trip but was unable to go for health reasons. She wrote the sponsor to let them know, and they generously sent her a $7,000 check instead!

-My friend Sonya said her favorite win was a once in a lifetime prize from a promotion called the “Chill Like Michael Jordan” sweepstakes. Being local to the event, she received $3,000 in lieu of airfare, a 2-night stay at the Ritz-Carlton, great seats to a Charlotte Hornets game, and a meet & greet with Michael Jordan himself!

As you can see, it’s quite possible to travel extensively, meet celebrities, and score some very nice amounts of cash by entering sweepstakes. It all depends on where and what you enter.

Taking up this hobby has allowed me to experience things and connect with people like I never would have before. Not only that, it’s served as the catalyst for something else- entrepreneurship and growing a business without having any readily available capital. Many of my cash and gift card wins go to buying inventory for my eBay and Amazon FBA ventures. It all goes hand in hand, as I describe in my book Flipping Free Finds.

If you’ve ever wondered whether real people actually win sweepstakes, I’m here to tell you that they absolutely do. I’m one of them. To date I’ve won upwards of $80,000 in cash and prizes, big and small, by casually entering sweepstakes as a hobby in my free time. And I never thought it was possible. My gratitude is overwhelming for everything I’ve received.

While I’m now a seasoned sweeper, I still celebrate every win, big or small, and I make it a point not to brag. This hobby has been nothing but a blessing-

And it started with a duffel bag.

2 thoughts on “How Entering Sweepstakes Changed My Life Forever

  1. Great write up. My first win came 60 years ago when I won a Goofy Grape watch from a coloring contest sponsored by Funny Face drink mix. Sure wish I still had that watch.

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