Don't get me wrong, though -- they're both good writers, so the above isn't a swipe at either guy or Hacker News.
However: "trailer-dweller" seems a little mean-spirited (and inaccurate) when it's clear who you are referring to with that example.
1) Are young and have started or been part of successful startups
2) Have blogs where they exhibit a strong personality through their writings, which are sometimes controversial but always tinged with elitism.*
3) Were/are darlings of Hacker News, with a high percentage of their blog posts making it high on the front page
*Not that there's anything wrong with that
Don't get me wrong, though -- they're both good writers, so the above isn't a swipe at either guy or Hacker News.
However: "trailer-dweller" seems a little mean-spirited (and inaccurate) when it's clear who you are referring to with that example.