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This is a repost from L’s blog, but I thought it would be good to share here too.  People always ask how I win so much stuff.  Well, it’s not just luck.  It’s work.  It’s actually very boring, but its pretty easy to sit on the couch and enter whenever you have some free time.  If you tell people you won something, they will almost always say, “Oh, I never win anything”. Yeah, well I wouldn’t either if I entered like 5 contests a year. Instead, I enter thousands.  In case you wanted to get started in sweeping, here are some secrets / tips:

1). I use the website www.online-sweepstakes.com. I pay for the Premium Membership, which runs $30 a year. I am sure you could find all the sweepstakes I enter at various places on the internet, however, I love the way they are grouped at OLS. The site is a little confusing at first, but you get used to it.
2). I do not enter contests for small prizes like books, cds, dvds, etc. unless I really really want them. It takes time to enter contests and I would rather focus on bigger items. I feel sort of the same way about blog contests. They get less entries so you have a better chance to win, but they are very time consuming (This is why I will always try to make my blog contests easy to enter).
3). I use a form filler program (if that’s even what you call it) from my internet browser. It fills in my name, address, phone number, etc. on contest forms. A few clicks is way easier than typing in all that info over and over again. This is different than the automated programs that are out there that will do the entering for you (most of these are banned in the contest rules and you will be eliminated if you use one).
4). I faithfully enter my “Daily” sweeps. If the contest allows you to enter everyday, then I enter everyday. OLS neatly groups sweepstakes into daily, weekly, monthly, etc. categories, which makes it so simple to keep track of. I think this helps me win things. Everyone has an equal shot if the contest is a one time entry. But you have a better chance of winning the daily ones if you enter 60 out of 60 times, because not everyone will enter every day!
5). I never pay to enter contests. Ever. The $30/annual subscription costs is all this hobby costs me (well, besides the taxes on the prizes). I never enter “snail mail” sweeps because I do not want to pay for postage.
6). I love the sponsors. Companies do not have to have sweepstakes and if people are not appreciative or if it becomes a pain for them, they will stop. I always send thank you notes after trips, mention brands I won from to friends, etc. I am always excited and grateful to win and I would never want a sponsor to think otherwise.  Also, if you don’t want the prize, don’t enter the contest.  There are tax implications on all wins, so consider that before you enter a trip around the world.  If you don’t have money to pay the taxes on a trip like that do not enter!  I never enter for super expensive trips on private jets, meet and greets with famous people, etc. because the taxes would just be crazy!

I hope this helps anyone who wants to get into this hobby.  I have to say, it has allowed us many opportunities we never would have gotten otherwise (have you ever gotten a private guide to escort you around Disney World?).  So start entering (a lot) and sure to let me know what you win.  Good luck!