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 income disparities, and even if the higher levels of income equality aren't driving the difference in quality of life, it suggests that higher levels of income inequality aren't driving improvements in overall quality of life either.
Graham correctly notes that producing useful things can be a source of wealth, and also incorrectly takes it to be be the only source of wealth. Large sums of money can be acquired by inheritance, unproductive activities like playing stock markets, and luck. (It is ironic that he uses Bill Gates as an example. According to legend, Gates got his big break because Gary Kildare went hanggliding)
Everyone is familiar with the idea that there is a relationship between productivity and deserved income, because everyone has been told that if they want a rise, t
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.