Who's judging anyone? He asked if he should leave his job to do a startup, I said "probably not" based on the fact that he's hesitating even though he has a really long runway.

Everyone tries to be realistic about risk tolerance. I'm more concerned about people who don't hesitate over big decisions than those who do.

Okay, fine. I'm more concerned about people who have 3-4 years of runway and still aren't confident enough to jump into a startup without first consulting a website full of strangers. To each their own.