At a dark table in the now-defunct Waldorf Hotel, two friends launched a year-long competition: enter as many free contests as possible and see who wins the most. The winner had to treat the loser to a free dinner at the Waldorf.

I was the one who ended up buying dinner.

Yes, after emerging victorious at the end of 2011, I decided to continue entering contests on my own. So far, I have won more than $3000 in cash and prizes.

Follow my winning streak and I’ll share all the amazing experiences I have along the way.