My rating: 2/5
I've skimmed the book briefly. Got audio version from youtube.
The whole point of the book is to discover loop holes in societies, systems, etc. Someone (Gladwell) who had submitted 100s or 1000s of applications for greencard lottery (old system) is sure to find David "broke the rules".
Creativity is not breaking rules.
Interesting source for political analysis, but I can hardly see Gladwell in a warm Christian fellowship manner. Christianity is not about how to be legal "cheaters".
The better biblical passage for his book should be Luke 16 of the shrewd accountant.
There is an audio book version of his book online. Some even free. Even that I lost interest listening half way.