I don't think he's mistaking what the Apple Fanboys will do, but I think he's mistaking how many of them there really are. At five percent, he's saying that more than half of Apple's userbase is made up of fanboys. In reality, the fanboys are really REALLY vocal (and annoying, and deserving of all the pain Jobs and Co. put them through), but they are a very sparse minority, and like you said, in not so many words, most of Apple's users are far more pragmatic than Tom gives them credit for.
Having said that, there are two technologies that give Apple a head start toward entering the search market:
1) They have been knee-deep in search on the desktop since Tiger was released. Windows search and Google search have been playing catch-up ever since. They have some VERY powerful technology under the hood of their own operating system, and the expertise to make it work, and the loyal following to get a foot in the door quickly.
2) Remember Sherlock? Before there was Google and all its relevant search results, the search engines of the world kindof sucked and were very hit-and-miss. Sherlock had some very good algorithms to take the results of all these engines, bring them together, and rank them for you. You didn't even have to be bothered with the ads (Sherlock filtered those out for you). Again, the technology is already there at Apple and has already been proven.
On top of this, Google's stranglehold on the search business is becoming weaker. With the close integration between Macs, iPhones, iPods, and iTunes, Apple has a very huge presence in most peoples' computing lives, and can very quickly disrupt that market.
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