"Maybe it’s my nature, but whenever I hear about a new initiative I start thinking about ways to game it."
Actually, it's not just Greg. I think this tendency is a fundamental law of the internet, similar to say, the 1st Law of Thermodynamics.
My statement of this law would be:
Anything created on the internet simultaneously creates proportional efforts to exploit it.
Pithy corollarys include (I'm quoting myself from back around 2002): "He who corrupts the blogosphere fastest and hardest will become very rich."
Who did that? Why Google, of course (via AdSense).