I think where Entourage went wrong is that it got lost in the noise. Until I saw the PE on Woot! I had no idea Entourage even existed. I really don't think joining an eInk and LCD display together in one unit was a mistake, because LCD is so limited in bright light. THAT is what they got right. Even if it did make the units heavier and thicker.
Fighting Google over the market was REALLY STUPID and probably contributed considerably to the disappointing sales. If half the perceived value of Android is the Market, losing that is a bad move unless you can CONVINCE prospective buyers you are replacing it and then some, and let's be honest, the Entourage Store DIDN'T. They would have done well to throw the MBA maggot that preached the gospel of "recurring revenues" off an overpass! (that's the Holy Grail in business school by the way -- the recurring revenues part, not being thrown off an overpass. There is no depth of he11 they will not cheerfully throw consumers into to achieve it!)
It's also early in the obvious Tablet Market life. Producing a product that delivers "more" but costs more is running upstream against consumer's tendencies to hold back and buy safe with a technology that is improving so quickly.
I don't know where Entourage focused their marketing -- it certainly wasn't anywhere I was looking. If they focused on academia, that was a mistake. They should have marketed to EVERYONE and then marketed to academia HARDER. Increased volume would have provided margin to compete with newer models on price (for a time).
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