Mathowie wins the MeTa thread here:

[...] The second, more philosophical problem is that he's kind of libertarian in the heady geek way lots of early internet nerds were and he claims not to go for the real crazy libertarian things, but it seems like as he is getting older he is skewing towards more and more libertarian rants.

He's got this op-ed column at the WSJ and every article there reads basically like "I have this crazy idea everyone should do the crazy stuff I did! Why isn't everyone doing crazy stuff like me and being awesome like me?! Why?!"

That seems to be the theme, and it annoys the shit out of me in the same way talking to libertarian-leaning uber geeks does, because most often I find they think of themselves as self-made men that pulled themselves up by their bootstraps that learned their own way of doing things and clawed their way out of college and into a career they mined themselves from raw bedrock stone. The reality is more like that old saying "born on third base and you think you hit a triple" where this mindset of a "self-made man" ignores the giant obvious perk of being born male and white and to a middle class or upper class family that bought you computers when you were young and gave you time and space to pursue your computer hobby to the fullest.