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I win a lot of free stuff in contests. Here are my secrets.

You might think I'm pretty lucky. I've managed to score tickets to festivals, local shows, and six-course dinners. And I've even won not one but two bicycles in my life.

My biggest contest-winning asset isn't luck — it's my experience advising companies that run contests. As a digital strategist, I've worked with clients that depended on contests to boost likes, comments, and follows on their social media accounts. And that has given me a road map for how contests work.

Running contests is one of the many ways companies boost engagement with their brands. A book giveaway can translate to a couple thousands signups on an email list or more supporters using an event-specific hashtag. Tickets for a show, easy to come by and ship out to a fan, can net companies hard-earned social currency.

Contest results aren't necessarily random — and if you understand how they work, you can boost your chances of winning.

Here are six rules I follow:

1) Think like a contest planner

Say you have a brand to promote and a big pile of something — like concert tickets or band merchandise — to give away. Your goal is to use the giveaway to get the brand in front of as many people as possible, generating the maximum number of entrants.

For brands that are still building a social media following, that's not easy. The number of initial followers who hear about the contest might be pretty low, and the number of entrants even lower.

That's a big problem for the social media manager. But it's an opportunity for fans, because it means that you have a pretty good chance of winning the prize — if you play your cards right.

2) Exploit social media, email lists, and hashtags

Your first step is to identify businesses, venues, or tourism boards to follow. Ideally, these will be in your local area, because who wants to win a prize you can't redeem?

  • For email, you just have to sign up with companies whose products you like, and contest opportunities will start pouring into your inbox. You can easily filter these using typical contest language like "enter to win."
  • If you're on Facebook, have a list of local accounts you check in on regularly, especially if you see a record of them posting contests on a regular schedule.
  • On Twitter, you may be able to find lists of businesses or influential accounts that you can follow in columns using apps like Tweetdeck or Hootsuite. Twitter also has a handy geotagging feature that lets you see tweets within a set radius of your location. Using Tweetdeck or an advanced Twitter search, you can run a radius search to find these local tweets. (For example, you can search near:"Washington DC" within:15mi in Tweetdeck or a Twitter search box.) Keep these in a separate column you can glance at over the course of the week.

3) Set up smart searches for contests you might actually care about

You might be following some promising accounts, but there's still a chance you'll miss opportunities amid all the online noise. To avoid this, you can set up pings for keywords that will help filter your tweets and emails. When running a search in Tweetdeck, I generally include terms such as "giveaway," "RT to win," or "win tickets" that are most likely to be included in a social media manager's promotion message. You could also specify a target item, whether it's a newly released book, travel, or electronics.

For example, in Tweetdeck you could search for "RT to win" OR "win tickets" OR "win tix." You can also run this a search for these keywords in the "any of these words" row of the advanced Twitter search.

Some contest enthusiasts have taken automating their entries to the next level, with bots that automatically retweet or enter anything with a contest ask, but I like to keep my criteria simple.

Once I've grown a significant pool of contests to choose from, I can get pretty selective about which ones to enter, focusing on my favorite musical acts or prizes I might actually use. I usually don't spend more than five minutes checking in on any of my given lists, and once I'm done I can just wait for a friendly social media ping or mention to inform me if anything has come of it.

4) Consider creating separate, contest-specific accounts

At this point, you're probably wondering if this means you're going to wind up getting a lot of spam or, even worse, wind up forcing contest spam on your social media contacts. If that prospect makes you queasy, there are several options.

One is to create separate accounts that you use only for contests. You might only check these once or twice a day — often enough to see new announcements but not so often that it drives you crazy.

You can also take advantage of filtering technologies, such as Google's promotions tab or Tweetdeck's filters, to filter out contest-related content from your primary account.

For email promotions, you can also add +promotions to your email address (example+promotions@gmail.com) as you type it into a signup form; then you can run a filter on all incoming emails with the appended keyword.

In some cases, you might also decide to use your "real" accounts. This might be annoying for you and your friends, but in some cases it might be worth it, because (as we'll see) contest promoters are more likely to choose winners with an active social media presence and more online followers.

5) Be the kind of person who gets picked

While some contest managers will pick a randomly selected winner, all too often the winner will be preselected and (as in the case of those "Dinners With Barack") heavily vetted.

Contest managers want a winner who promotes the brand, is excited, and will spread the word to his or her followers after winning. For social media contests especially, there's a big benefit to choosing a winner who has a decent personal following. Often the rules favor those who best represent the brand by meeting some arbitrary criteria for the "best" comment or entry.

This is one reason using your real accounts might give you a better chance of winning than using a secondary account. And at the end of the day, actually sounding excited about a contest will probably help you get picked, or at the very least make you a much more appealing prospect for a contest down the line.

6) Bet big on openings, first-time festivals, or up-and-coming acts

Music is an area where savvy contest entrants can really shine. Following local venues, artists coming to town, or first-time festivals reaps the easiest rewards. Promoters are eager to fill up shows, and throwing a contest is an easy way to get buzz for the band or venue. Plus, a contest winner might be likely to get a few more friends to tag along or spend money at the venue on alcohol or promotional items, a win-win for everyone involved.

Bands and authors will also likely count on the types of swag that are easiest for them to distribute, from digital downloads of books or music to signed hard copies and merchandise. Just make sure it's something you'd actually want to own.