Consider that despite his wealth and lifestyle, he seems to have a substantial inferiority complex and thus the need to shit on everyone else who didn't literally win the daddy lottery. This likely stems from the fact that he wasn't rich when he was a kid. His dad was already doing well by the time he was a young teenager, but he had a fairly normal UMC tri-state upbringing. It wasn't until the 9/11 litigation that his family was suddenly very wealthy and living on a completely different level, and he was 18 or older by that time.

So that happened around the period when he went to college, and he clearly just went off the rails and reveled in the fact that he would never really have to worry about anything. A look at his "travel blog," authored after he graduated from college, will show you the mind of a very immature and distracted person. Frankly, he comes off like a raging dolt, even for a young guy without much cultural enrichment.

There's also the tragic death of the brother from drugs, forced to transfer schools due to sever flunkage, lifetime of weight struggle, creeping insecurity over lack of personal accomplishment, etc. It's terribly obvious that he's been a serious binge drinker for more than a decade and relies on alcohol for his social persona and comfort level. This is typical for high school and college kids, but not a grown man in his mid 30s. His preference for really prole booze and party habits doesn't necessarily speak to that point, but I recall old threads where he would catalog his drinks like some kind of bumbling Tucker Max fanboy. Normal, secure dudes don't really do that kind of thing past college, if ever.

You can tell there's a piece or two missing whenever he is forced to discuss personal relationships of any sort. He reflexively and defensively starts calling any and all posters "aspie" or "virgin" in these circumstances, but his total inability to articulate his social attachments and the emotional underpinnings of his life choices indicates strong aspie leanings from his side of the ball. He sounds like a baffled and posturing teenager whenever he's required to go an inch beneath the surface or explain his personal motivations. And that's on the rare occasion when he can tamp down his anger long enough to honestly address a critique or question. And that truly is a rare thing, because when poasting, he's never not insanely angry and defensive, usually fueled by booze. It's standard aspie internet rage, but lacking one iota of self-awareness. And finally, the obsession with flying, travel details, and pretty much everything about his travel interests via his failed blog all scream 'detail-obsessed aspie.'

The guy has some problems, and anyone familiar with his posting would agree. Half the time he's here, he's drunk and aggressive, truly just looking to trash people with less money and good fortune. A well adjusted person doesn't make a years-long habit out of that kind of thing. All the exaggerating, despite his great life, also indicates some deep-seated unhappiness and a desire for recognition that he simply doesn't get out there IRL. We are talking about a guy with functionally unlimited free time and opportunity to life life at 100 MPH, but instead he spends his nights megapoasting, screaming at benzo/uvt/other board freaks, and complimenting himself with sockpuppets.

I would go so far as to guess that outside of his loose circles of party friends and travel acquaintances, he's very lonely and unfulfilled. That would explain the painful stabs at blogging, the going-nowhere-fast 'start-up' he created and then forgot about, the endless traveling for its own sake, and other habitual time wasting that makes up most of his day-to-day life. The guy never developed himself personally during his formative years because he was newly rich, young, and dumb. You can kind of see that he's a witless and dull instrument when he tries to verbally spar with anyone on XO. Now, in his mid 30s, he's a very modestly educated fat rich guy with no direction who lives off what is functionally an allowance from his father. He doesn't even try to defend the partnership thing in his dad's firm, which I suppose projects a tiny bit of awareness on his part.

That's not all to say he's seriously mentally ill. But yes, he has some real and observable issues. Fortunately for him, he can continue to pretend they don't exist by responding to this post with "dork" and "virgin," hallmark examples of the stunning intellect and razor insight gleaned from years of unlimited resources and the ability to do anything he wants to develop himself into a fully functional human being.

(http://www.autoadmit.com/thread.php?thread_id=3119445&forum_id=2#29759244)