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Some hits, some misses. It's hard for anybody to say with authority just how many should have been hits but were not. I think it's unrealistic to expect ALL of them to be a net win. Nobody can predict the future, not even Google.

NOTE TO SELF: start a web-based service that successfully predicts the future. Sell out to Google.

I recall people panning the purchase of grandcentral because of the incredibly long delay between purchase and launch of Google Voice...

It is hard to tell what purpose a company is acquired for (talent, technology, marketshare...) and thus difficult to tell whether it was fruitful.

Dodgeball's a commonly cited failure. The founders left two years after being acquired to start a very similar competitor, which even has a hilariously similar name (Foursquare), and then Google discontinued Dodgeball two years after that.