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Hopefully he can bring a working monetization model with him.

I think Jack will concentrate on the product, the monetization part will be left to Dick Costolo.

Can the two really be separated like this?

Yes

Are there any historical examples of it working?

What happened to Ev? I thought he was supposed to be the product guy.

Ev is involved less and less (from the TechCrunch article). Maybe he is preparing for his next venture.