Wow, never read this one back in the day but this is very good. In Praise of Evolvable Systems by Clay Shirky from 1996 is kinda technical but so right on about why "the internet", which is what we call a bunch of web servers, is the way it is.

Also, interesting and more current, is his analysis of why, in the world of weblogs, where there was supposed to be not 500 channels but 500,000,000, it turns out that there are less than 5. Read Power Laws, Weblogs, and Inequality and find out why nobody reads this blog. (I'm not complaining. I'm now fully aware of the power laws at work.)