Secrets to winning loads of free sh*t

Gone are the days of clipping labels, returning Publishers Clearing House’s letters, and waiting for Ed McMahon to appear at your door. Thanks to the internetz, sweepstakes are faster, better — and exponentially more addictive. Take our friend Ryan, who figured out how to enter upwards of 300 contests a day in a matter of 30 minutes. “I was just kind of bored one day. I entered this contest, and I won a gift certificate, like that. Then, I got into it. I wanted to see how much I could win,” he says. To date, he’s scored a $100 Office Depot gift card, some American Apparel clothing, laptop accessories, and a recent $100 Fairway gift card. We tapped him for some pro advice on gaming the giveaways. 

First, a word of warning: Most contests will only ask you for your contact information. Do not give away any bank information or personal data. Also, always read the fine print. Some contests may sound awesome, until you realized you’ve signed up for a trial subscription to Boats & Cowboys magazine.

CREATE A SECOND EMAIL
Expect at least a moderate spam uptick — an occupational hazard of entering contests. “Most people use an alternative address for sign-ups but you have to still check it frequently because that’s also where you get winner notifications,” Ryan says. “I just have it come to mine. Google catches most of the spam, and I used to search the spam box a few days a week for keywords like ‘winner,’ ‘congratulations,’ and shit like that before deleting everything.”

CHECK THE SITES
Contests.about.com is numero uno on Ryan’s sweeps site picks: “It’s updated daily; which really helps. It’s easy to navigate and when there’s a contest that has more than one sponsor they list all the links where you can apply.” The site also offers tips on avoiding scams, and has a kicking forum that helps when you hit it small or hit the jackpot: “Some people win three cars and it’s no big deal to them. They are on the forum figuring out how to turn it into cash, by selling it back to the dealership that they won it from,” Ryan says. That person winning three cars could be you.

Highlights of current offers: Mekhong – Full Moon of Thailand Sweepstakes, Two Nights in Thailand for four during the Full Moon Festival  (airfare included)

Online-sweepstakes.com compiles a list of everything going on, and provides you with a “MySweeps” tab to keep track of all your entries. Their forum is super valuable with a newbie forum and a swap forum. The swap comes in handy since a majority of the list are smaller prizes, like a signed Maroon 5 poster. Hahahah.
Best of the current offers: Actually, the Maroon 5 poster. Or maybe this flip cam.

Sweepstakeshub and WinPrizesOnline were both featured on Good Morning America yesterday. WinPrizes has a great collection of prizes, but most importantly, has a freebie page that includes coupons for free Shout, yogurt and tea. Sweepstakeshub, on the other hand, has a lot of crazy-big-name prizes: win a soccer trip, win $10,000 and Kikkoman products, win a million dollars from Oprah! The competition may be high, but you know, someone has to win.
Best of the current offers: A Million from Oprah, and a six-night trip to London and Paris

GET AN AUTO-FILL PROGRAM
At the height of his sweepstakes entering (he’s since dialed back a bit), Ryan would be applying to up to 300 sweepstakes a day. “It would’ve been impossible for me to enter so many forms everyday. I would definitely recommend using a program like Roboform, or 1Password. Their lite versions are free and do everything you would need them to. I could come home from the bar, and enter a bunch of contests in no time.” These programs use macros to automatically fill out all the forms. For those with Google Chrome, lucky you, they already have this feature.

TAKE THE EXTRA STEPS
If the contest involves writing an essay, using a skills, or collecting UPC number, do it! Anything that involves more effort than auto-filling your information into a form, fewer people apply.  Ryan says:“If you needed a UPC label say, from pickles, some of the guys in the forum would make a note on their shopping list to check out the pickles, and write down the UPC number. This way they wouldn’t have to buy them, and they could still enter the UPC number for contest online.”

Good luck, sweeps heroes!  If you know more good sites, let us know in the comments.