[gomberg]

It seems this is a function of how much you'll get from a continuation bet vs. hoping he has a big hand.

If he has a big hand (any pair pretty much), he'll probably at least call a flop bet and / or raise. If he doesn't he could fold or call and try to take the pot away from you on the turn (or he may hit an overcard and play for a cheaper showdown).

I think the best way to stack him is to bet out, but I'm not sure it's the most +EV play here (read, you won't stack him too often but will get some bets out of him a lot of the time). He will at least fire a continuation bet though.