And it wouldn't be half as annoying if their stuff, you know...didn't suck.
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Still, it can work: look at, say, their Project Management application (imaginitively called Project): it started as a easy-to-use featureless toy that sold for almost nothing, and then (via six version iterations) eventually overtook the (originally) much better and entrenched market-leader Computer Associates product.
That's when they get it right.
Otherwise there is MSN Messenger or their Search, as counter-examples ...