If you wouldn’t mind seeing a few more PRIZES in 2008, this is for you! Dr. Jay Sokolow is a radiologist in New Haven, Connecticut who’s won more than 2,000 contests and sweepstakes! His prizes have included Super Bowl tickets, iPods, computers, cell phones, Caribbean cruises, golf trips overseas and many more. He enters the contests in his spare time, and gives many of the items he wins to family members, friends and charities. He’s become somewhat of an “expert” on winning, and says YOU can, too! How? Here are his tips, courtesy of the Bottom Line Personal. For starters, Sokolow says he enters contests that fit the following criteria:

  • They offer several consolation prizes in addition to the grand prize. For example, you may not win the grand-prize Super Bowl trip, but you could win the big screen TV as a runner up prize, or a $100 gift certificate to a sports store.
  • He enters contests that have short entry periods. No longer than a few weeks. Why? The longer a sweepstake is available, the more people enter it. So, once you’ve entered a contest, here’s how to
    improve your odds of winning:
    • Submit multiple entries. Most sweepstakes allow different people from the same address to enter – so get the whole family involved.
    • Always read the rules. You might get disqualified for entering too early, your address is a P.O. box - which many contests won’t accept, or you didn’t fill out the form correctly. So, make sure you look it over when you’re done.
    • Keep records for taxes. You need to report any winnings of $600 or more, BUT you don’t have to list the estimated value of a prize. You’re allowed to make a “fair-market” adjustment. For example, let’s say you win an iPod that the contest sponsor values at $300. Then you find an ad in the paper for the same iPod for $200. Hang onto the ad, and use that value on your tax forms.

Wanna start winning? Sokolow says check out SweepsAdvantage.com. It’s the Web’s largest sweepstakes directory – and it’s FREE.