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.
