My dad likes to say, "even a blind squirrel finds an acorn now and then." And it's true. You shouldn't pick your strategy by modeling someone else's success. The success might have been strategic and planned, but it's just as likely to be a matter of blind luck. Someone had to get that big deal, and this time it was him.
The numbing reality of the net is that now we can see all the blind squirrels, all the time. A recent piece in the Times talked about bloggers getting six figure book deals in just a few weeks after posting community-driven goofy websites. It's easy to read this and say, "I should do that! I could do that!"
What's missing from the article is that for every 10,000 goofy websites that get launched, one turns into a six-figure book deal and the other 9,999 fade away. If you want to build a goofy website, go for it. Just don't expect to be the lucky squirrel.