Now, this one is a tad tricky. I have a few tips, however, if you want to win it (which I have done, twice):
1.) The more time on the site the better. If you only get on to feed your pets, play games, and get money, then forget about winning. You have to be updated on everything, like new items and other games.
2.) Things that have just been introduced will be on there a lot. When I won the last time, I just got on and said “Oh! That’s Hubert from the Hot Dog Place!” I just typed it in, and happened to be one of the first 500.