Care to explain this a little more?

Jeff talks publicly all the time about how much of a fuckup he is, how proud he is that he sort-of figured out something you thought was obvious, how he just can't do anything right. It's his public persona, and the subject matter for his formulaic blog, where posts usually end with an explicit confirmation that it was a waste of your time: http://blog.wekeroad.com/blog/nothing-to-say/

He doesn't talk so much about what a successful badass he is (see Joel), despite obviously having accomplished some pretty major shit.

And all of the above presumably helped him to co-found a successful (in a make-something-people-want sense) startup. Not too bad after all, eh?

I disagree with the grandparent poster because it doesn't matter if you come off as a bumbler or a chancer in this environment - actually, Atwood's gungho informality is probably a plus. But I suspect he's getting at Atwood being routinely wrong or misinformed about all manner of developer related topics - just listen to the Stack Overflow podcast for a few weeks to get a feel for it. Joel's routinely correcting him on stuff that's not even in Joel's area of expertise. (But that, versus someone who's scared of ever looking wrong? I think I'd invest in Atwood.)