The point I was trying to make is actually entirely unrelated to the issues you've raised. My goal was not to turn the tables so much as to illustrate that the use of the word "deserve" in this context makes the question inane because it's moralistic.
In any event, the fact that beggars can't be choosers does not obviate the importance or utility of posing some form of the question to the prospective investor.
That makes sense and those are good points. I think it’s about tone all the way around. It’s entirely fine and beneficial to both parties for the startup to ask questions. But there are some distinct differences in how people ask these questions. Some really are stuck up. It’s shocking how deeply people can believe the stories they’ve made themselves about how good they really are when in fact they failing miserably.
Some of the better questions I’ve heard are prefaced with comments like “we’re aware we’re having troubles in this operational area, would you be able to offer guidance and advice to get us out of this sticky situation?” Self awareness seems to be a sign of a great and investable company.
For many of the founders I talk to would say their startup "deserves" more money because of what they have accomplished. I'm simply trying to use the same language founder use with me.
In any event, the fact that beggars can't be choosers does not obviate the importance or utility of posing some form of the question to the prospective investor.