I realize that Jason Kester believes the customs officials are offended when he gloats about his globetrotting, but you know, they probably aren't. The likelihood is that they hear stuff like this dozens of times a day from happy, excited people who have just come home from extended travels. "Oh, yeah," they think, "that's nice."
They're probably a little annoyed that Mr Kester has negligently not bothered to retain the first half of his ticket, failed to deep track of when he left or what countries he visited, and was too stupid to fill out the paperwork properly. They may even roll their eyes thinking he's a bit of a smelly pig not to have changed his shirt in over a month and wonder why he couldn't afford to have more than one.
I'm pretty sure they don't give a crap about his software company, or have any use for his product, either. They're probably pretty content in knowing they have the federally mandated power to just just glance over at the big guy off to the side and within three minutes, Mr Kester will be bent over a table in another room with a couple of rubberized fingers up his ass.
If Mr Kester thinks he's making customs officials feel small and unimportant because he has such an "exciting life", or that he's in some way "evening the score" by bragging about having been in the Far East for over a year, I must say that "this sort of treatment" is rather too subtle for thick-skinned customs staffers. They really couldn't care less where he's been or where he's going, as long as he isn't carrying any contraband.
If he really wanted to make them feel that they're so much worse off than he is, he'd have to add, "... unlike you, with your shitty, dead-end job, sitting in a little cube," or some similar direct comparison. But that would probably get him taken into the other room.
Finally, I'm willing to bet that the agents aren't regular readers of Hacker News, so they haven't seen Mr Kester's post. In this case, ignorance is bliss.