I really like the "culture matters" and "look stupid" posts. I've been allowing myself to look stupid since I was a kid in school. Dan is humble (frequently saying things such as "If an idiot like me can [do X]"), but I think this strategy requires a certain degree of intellectual security. For me the logic isn't just "this question may sound stupid but the knowledge gained outweighs that". It's also "this question may sound stupid but anyone who thinks I'm dumb is wrong".