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At least 100 times a year, a box lands on my doorstep, bringing more free goodies into my life. Today, it was a set of seven DVDs. Over the last decade, I’ve won approximately 1,000 prizes–more than $100,000 worth of stuff–through my hobby of entering sweepstakes, giveaways, and the occasional genuine contest.

I started in grade school, filling out three-by-five cards and mailing them in to contests I came across in magazines and on product packaging. I was eager to get something for nothing, motivated by the thrill of anticipating a possible windfall. We lived on a remote island off the coast of Georgia, so my parents indulged my interest and kicked in the postage. As I started to win items of value, my efforts increased. I’d tapped into the excitement of gambling, without the risk of loss.

With mail-in entries, I’d figure out whether the value of the entry exceeded the cost; if a sponsor was offering a $5,000 prize and expecting 100,000 entries, then each entry would be worth only $0.05 and wasn’t worth the postage. The Internet changed everything; one could enter for free, and smaller sponsors could offer prizes without having to spend as much on advertising and promotions. These days I rarely mail in an entry.

My friends say I’m lucky, but I credit persistence. I spend about two hours a day, on average, pursuing prizes online; I usually net between $10 and $15 an hour. In exceptionally lucky years I’ve raked in more than $50 an hour from my hobby. I wish I could say that my MIT education enabled me to construct a contest-entering robot, but my methods are decidedly more low tech. I bookmark links to contests, repeatedly type my name and address, hit “send,” and hope for the best. A background in science and engineering does, however, come in handy with the occasional trivia contest, and it helped me understand a local radio station’s phone system. I discovered that WFNX had only three incoming lines when I didn’t hang up during a call-in promotion. Upon hearing, “Hello, you’re caller five … Hello, you’re caller eight … Hello, you’re caller eleven … ,” I deduced that the station always answered the three lines in succession. So if they were looking for caller 13, I could win not only as caller 13, but also by staying on the line as caller 10, seven, four, or one. Unfortunately, the station has since moved to a more modern system.

Thousands of contests are always under way, so I get two publications to keep up. I never bother with Publishers Clearing House, given the hopeless odds. But over the last several years, I’ve won seven trips (including jaunts to Los Angeles for the Soul Train Music Awards and to a Miami Beach spa), a Vespa scooter, Green Monster tickets at Fenway, several pieces of stereo equipment, and a fair amount of cash. My coworkers were thrilled when I won a month’s use of a chest freezer, which was filled three times with ice cream–more than 120 quarts in all.

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Credit: Eric Levin

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