Tom has been to the Super Bowl multiple times. He goes on free cruises yearly, has ridden on the Daytona 500 track at 200 miles per hour, traveled with the U.S. soccer team, and devoted a room of his house to store all the Reese's Peanut Butter Cups and big screen TVs he's won over the years. That's because he enters more than 100 sweepstakes every single day, and thanks to a constant supply of free gift cards, he rarely pays for gas, cable, or his cell phone out of pocket. But he's not a wizard or a scammer. He's a Sweeper, and he's built a community of like-minded folks who share sweepstakes knowledge from around the country to beat the odds and get free stuff.

Alli and Jen get his tips on how to win, and learn about his journey from free fries at Burger King in the '80s to running a sweeper newsletter at iwincontests.com.

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