The problem with drawing a circle is that it interferes with ordinary drag actions. How would Google Maps know whether you meant to drag the map or were trying to zoom?
I don't think Chris Dixon is necessarily saying that founders are better, more worthy people than non-founders. I think he's just saying that being a founder is super hard.
I agree with you that there are many paths to happiness :-)
Time is valuable. Why waste everyone's time if you know it's not going to work? I think the key is to do it respectfully and explain why. It's actually helpful for the company to hear the reasons.