I think people in silicon valley often forget how privileged they are. The application question is basically asking
What have you personally done in your life? Why should we give you a chance? I think Bryan Cantrill suffers from a lack of perspective. Like if you ask Taylor Swift about how to be a successful artist and she says just follow your dreams and everything will fall into place, I imagine Bryan hasn't had to justify his personal contributions anywhere in a long time likely because they are just obvious and do easy to see. Now compare that to someone like me who has only worked on line of business applications. I try to be honest which in my mind sounds like I'm being humble but from the other side it just sounds like I'm unaccomplished and have poor listening/comprehension skills.
In any case, I think this thread needs to be less about Bryan Cantrill and more about YC.
Bryan Cantrill's Wikipedia page says he asked a kernel developer if he had ever kissed a girl as a one line reply to a technical discussion. My instinct whenever I hear accusations like those by Valerie is to say maybe there's a different perspective but I don't think there is one in this case. Regardless of all this (and his association with a company that stupidly offers lifetime hosting to paying members and later yanks it which is essentially fraud), I think the arguments he makes stand on their own. These aren't arguments I could make because I'm a nobody but I'm glad someone is making regardless of how flawed they are.