I advise my friends to do the same, but often realize that like you have found, they aren't really equipped to ask the question in an effective manner even if I tell them what they need to ask.
In that light the "assume your equity is worth zero" really starts to be a good self protection mechanism.
That's the approach I take. I tell them that I will think of their equity like a bonus, and I will be happy to work hard in anticipation of getting something from it, but probably will not trade real dollars in return.
In that light the "assume your equity is worth zero" really starts to be a good self protection mechanism.