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It takes a special kind of person to be able to live entirely on coupons for a year, or even to attempt it. Most of us would either scoff at the idea or contemplate it very briefly before inching back to saner endeavors, but Josh Stevens has long been destined for this kind of absurd challenge.

“I’ve always been a deal-seeker,” the 27-year-old told MainStreet. When he was still in his teens, Stevens forced each member of his family onto a group phone plan rather than paying for individual phone lines, long before family plans were popular. He has spent long nights camped outside Best Buy to buy a Wii and a PlayStation 3 the day they came out just so he could resell them online for a heavy profit. “When the Xbox 360 came out, I waited outside the store for at least a whole night and then sold one of them online for $5,000,” he said. And why? “I just find it really fun, like a game.”

So when Groupon, a popular Web site for coupons, announced their “Live Off Groupon” challenge in February, Stevens jumped at the chance. But really, to call it a challenge is putting it mildly; this is a mission designed to make contestants sweat. Groupon requires the “lucky” winner to give up all worldly possessions for a year (including his home, job and family) and find a way to make due on nothing but coupons and ingenuity. If Stevens succeeds, he will be rewarded with a fat $100,000 check at the end of the year.

Nearly 400 people applied for this opportunity, by creating YouTube videos explaining why they were the best candidate. The winner was supposed to be announced at the beginning of this month, but that date was pushed back. “The reason for the delay is that we have absolutely no idea what we are doing,” Andrew Mason, the CEO and founder of Groupon, told MainStreet. “We thought of this on such a whim and now we are grappling with the enormity of the task.”

Nonetheless, Groupon narrowed the field down to six finalists including an unemployed woman with no boyfriend or home and a butcher who had dreams of becoming a photojournalist. Ultimately though, Stevens beat them all. “I was definitely surprised and very excited,” Stevens said about being selected. At the time, he was waiting tables at a “fine dining restaurant” in the suburbs of Chicago, and busy applying for MBA programs.

“As soon as we saw his video, we were smitten with Josh. It really stood out from the pack,” Mason said. The video in question is an over-the-top scene in which Stevens embarks on his Groupon adventure only to end up using printed-out coupons to battle a bear. (It doesn't make a lot of sense to us either, but the judges loved it.) Stevens said his first thought when brainstorming his Groupon application was, “What would MacGyver do?” So he attempted to mirror his entry with the opening credits for the popular show.

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Stevens may have won Groupon’s heart early with the video, but he still had one more obstacle left. Each of the finalists had to visit Groupon’s Chicago headquarters and do a trial run, trading in their wallets and living on coupons for an afternoon. The test proved so difficult that one of the finalists dropped out right then. But Stevens excelled in this setting. He hopped on a mail truck to travel around the city, paid for a cab ride with a cookie and a $5 gift certificate, and even got a Lego souvenir of the Hancock building by giving a “nice lady” a coupon for free admission to the landmark. All in all, he demonstrated to the judges what he had always known about himself: he was able to make cutting corners seem fun.

"In the end, the consensus is that Josh was the man who was most likely to survive and be the most entertaining to watch try and do it,” Mason said. But even Stevens admits that there are some difficult steps he has to take now. He currently rents an apartment in Chicago but his lease isn’t up until the end of July. “It’s difficult on such short notice to find someone to sublease,” he said. “So I’m trying to get out of the lease earlier.” On top of that, he’s only allowed “limited” visits with his close friends and, perhaps more importantly, with his girlfriend during his yearlong adventure. “It’s not ideal, but the rules are the rules.”

The rules are tough, but Stevens has many people rooting for him, including friends and fellow Groupon users.

“I do hope that he makes it through the year, but I hope that it isn’t too easy. I want him to suffer a bit,” Mason said, but then clarified his statement. “I want him to suffer just a little bit.”

Stevens is prepared for the challenge but he already has some bigger goals in mind for his life a year from now. He hopes to parlay his exposure into a career as a food critic. “I’d love to get a spin on my own show or to write a book,” he said.” But Stevens also said he’d be interested in working at Groupon, though Mason has privately warned Stevens that he may not even want to hear the word Groupon in a year. And what about the $100,000 prize? “I’d like to use it for a down payment on a home and possibly to go to grad school.” He may be a frugal fanatic, but Stevens knows how to spend wisely.

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