The whole tone of the post struck me as something like, "Hey, it's not like I'm just some stinky nerd." He's got a girlfriend, knows Mark Pincus, can afford a lifecoach...why shouldn't he be a business success? However, I didn't see any reflection on the fact that he's running a coupon site and whether that has something to do with his seemingly-persistent frustration.

Whatever the root cause is, at the end of the day it's something that prevents him from noticing the typo on the AppSumo front page, so the level of detail of self-examination in the post seems to be somewhat opposed to the level applied to the mechanics of the business itself.