[Padawan Learner]

Deranged:

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Think about the mathematics of semi-bluffing here:

With 8 outs to the nuts here and possible clean overcards, let's estimate your total number of outs at 10-12. So your chance of improving here will be between 22-26%. We'll use 24% for estimation.

Let's say your opponent will fold to the turn raise with frequency "f."

Then for the semi-bluff to be profitable you need to satisfy the following inequality (let p = pot size before your semi-bluff raise; namely, including the bet and your call on the turn but not the raise). We exclude the effect of implied odds and the possibility for villain to re-raise the turn. We also do not yet consider possibility hero hits a K or Q and loses.

f*p + (1-f)(.24p - .76) > .24p
.76f*p > .76(1-f)
f(p+1) > 1

In other words, your fold equity (f(p+1)) has to be greater than the cost of the bet. Given the pot size, opponent will be needing to fold here like 14-15% of the time for your play to be profitable.

So the question is not really one of "never." It should be one of "how often." Don't worry if your semi-bluffs seem to often not work... they're not supposed to. If you actually get the sense that they are "never" working (like < 10% of the time) then you should cut down on them.

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Excellent post...very helpful.

So, given my situation, you don't think he folds 15% of the time?