Fun fact: many modern email clients use a version of the bayesian spam filter Paul Graham proposed in a 2002 paper (itself an improvement on an earlier bayesian spam filter).
cue one of us, one of us
My personal faves are Mind the Gap and How to Make Wealth both of which I use to introduce many econ topics to people.
Mind The Gap is actually among my least favored essays, since I think that Paul Graham, coming from the position of someone who's made all his money working with startups, isn't giving adequate consideration to the ways in which business leaders can accumulate money without being high overall wealth producers. Also, he suggests that great income disparities in first world countries are positively associated with the health of those societies, but those first world nations which score best on various quality of life metrics tend to be those with lower incom...
This isn't really a full post, but merely a note of potential interest. Paul Graham (who runs Hacker News) has several very interesting and thought-provoking essays located on his personal website. To me they fit very well with the style of thinking employed and advocated by many people on LW and I'd advise that nearly anyone interested in LW check out his work.
I especially recommend Keep Your Identity Small, What You Can't Say, and What You'll Wish You'd Known, but nearly every essay up there is interesting to me in some way. Many of them are directly relevant to issues of rationality, while others are only indirectly related, but either way I found them worth my time.