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The problem I'm having with it is he has to know this guy does this. It's not exactly subtle or I likely would not have noticed. He's been in the room before when it happened, and the two of them go out for drinks on Fridays and such all the time. I think it is not a problem for him or he would have pulled the guy aside and told him.

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He may be in denial about other people's perceptions. You talked about bringing it up after you have an escape plan - make sure you're bringing it up with the boss too.

You should probably find a new startup to join/start.

That's my plan actually. Once I have nothing to lose I'm going to tell the guy he's being an asshole to the women engineers and ask if he'd consider not doing that because it's a shitty way to treat anyone. Preferably with boss present.

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