The OP says: That’s not what I meant. I know YC is a great place. But why do YOU want to get in?
I don't think he was being as critical of the path chosen but more so of why the friend decided to start the journey to begin with. I might be misinterpreting things though.
"Listen. It’s never been easier to start a company. And right now, money is thrown left and right. In the past year alone, six of my colleagues left my company to start their own startups. I figured if they can do it, I can too."
OP didn't like that answer and skipped past it, and I'm playing psychoanalyst by wondering why.
That answer was a "me too" answer isn't it (not arguing the merits of a response regardless of whether it is or isn't). I think the author (I'm guessing) was hoping for a deeper answer than "I'm doing this because everyone else is and it appears easy" rather than simply skipping over it.
I don't think he was being as critical of the path chosen but more so of why the friend decided to start the journey to begin with. I might be misinterpreting things though.