This post about a LW meetup that he attended is probably relevant.
I personally find Venkatesh's blog very interesting, but am somewhat skeptical of a lot of his particular ideas. He has very cool posts about some historical things, like the importance of modern shipping containers, history of the corporation, and the importance of barbarians. Those are all seriously awesome, IMO.
I also found that his idea of legibility crystallized something I kind of knew before, but not particularly in words. Basically, you have some stuff that follows rules imposed on it (legible) and things that arose organically with lots of local adaptations, that is much harder to understand. Legibility is in the eye of the beholder, and learning thoughts or having particular ideas can make some things legible that weren't before. If you optimize too hard for one particular thing, you get something that's legible but largely useless, if you don't try to impose order its difficult to manipulate.
I'd take issue with the phrase "his idea of legibility". What Rao is doing in that post is summarizing Scott's excellent book on that same topic; it is of course a valuable service to intelligently summarize a book, but it's hardly the same as coming up with the idea in the first place. (I was turned on to that book by a guy named Michael Bolton, who I think is a pretty extraordinary thinker in his own right. Rather than write a post about Scott's book he's only been going around ordering everyone he knew to read the book.)
Venkatesh Rao (who is amazing because he literally constantly challenges our definitions of everything):
http://www.quora.com/Venkatesh-Rao/Quora-Portfolio-Year-1
http://www.quora.com/Venkatesh-Rao
http://www.ribbonfarm.com/be-slightly-evil/
http://www.ribbonfarm.com
Gregory Rader:
http://www.quora.com/Gregory-Rader
http://onthespiral.com/
Daniel Lemire:
http://www.quora.com/Daniel-Lemire and http://lemire.me/blog/ are also super-super-super interesting
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I tried doing google searches of site:lesswrong.com + their names (or websites), but ended up with little. I'd like to see what LessWrong thinks of Rao in particular. I have NEVER seen posts that were as amazingly insightful as his. It's worth it just to sacrifice a day just to see all his amazing posts. The others were also amazing and really make you think about everything.
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E.g. with Rao, you have
My favorites:
http://www.quora.com/What-are-the-benefits-to-obtaining-a-PhD-in-the-field-of-Education/answer/Venkatesh-Rao?srid=0WH
http://www.ribbonfarm.com/2010/05/19/intellectual-gluttony/
http://www.ribbonfarm.com/2011/04/07/extroverts-introverts-aspies-and-codies
http://www.quora.com/What-careers-or-industries-are-the-most-meritocratic/answer/Venkatesh-Rao?srid=0WH
http://www.ribbonfarm.com/2008/09/11/how-to-measure-information-work
http://www.quora.com/What-are-some-tips-for-advanced-writers/answer/Venkatesh-Rao
http://www.quora.com/Children/Why-do-some-humans-not-want-children/answer/Venkatesh-Rao
http://www.quora.com/What-is-the-best-way-to-motivate-oneself-to-finish-a-PhD/answer/Venkatesh-Rao
http://www.quora.com/History/What-is-the-most-important-human-decision-ever-made/answer/Venkatesh-Rao
http://www.quora.com/Is-the-following-follower-model-the-new-standard-of-social-connection/answer/Venkatesh-Rao
http://www.quora.com/What-discipline-specific-principles-help-reframe-activities-so-as-to-provide-useful-insights-and-or-improvement
Rader:
http://onthespiral.com/stop-wasting-time-and-effort-developing-fragile-capabilities
http://onthespiral.com/unifying-value-universe
http://onthespiral.com/principles-disruptive-learning-environments
Lemire:
http://lemire.me/blog/archives/2010/08/16/working-long-hours-is-stupid
http://www.daniel-lemire.com/blog/archives/2010/02/08/trading-latency-for-quality-in-research
http://www.daniel-lemire.com/blog/archives/2009/09/14/how-things-change-cheaters-are-innovators
http://www.daniel-lemire.com/blog/archives/2008/08/19/the-secret-to-intellectual-productivity/
http://www.daniel-lemire.com/blog/archives/2010/01/13/the-fundamental-properties-of-computing/
http://www.daniel-lemire.com/blog/archives/2007/12/05/formal-definitions-are-less-useful-than-you-think/
http://www.daniel-lemire.com/blog/archives/2007/11/19/directed-research-is-useless/
http://lemire.me/blog/archives/2006/08/09/big-schools-are-not-longer-giving-researchers-an-edge/
http://lemire.me/blog/archives/2011/06/23/probabilities-are-unnecessary-mathematical-artifacts
http://lemire.me/blog/archives/2011/06/14/the-language-interpreters-are-the-new-machines
http://www.daniel-lemire.com/blog/archives/2009/08/01/why-i-hardly-ever-blog-about-my-ongoing-research/
http://lemire.me/blog/archives/2011/06/08/is-wikipedia-anti-intellectual
http://www.daniel-lemire.com/blog/archives/2008/06/05/why-pure-theory-is-wasteful
http://lemire.me/blog/archives/2011/06/06/why-i-still-program