Nerds vs. Jocks
I found the opening chapter to be exceptionally insightful. Graham discusses in detail the culture of being a teen, particularly a teen in a public school setting, and what sets nerds apart. His description of the sort of "Lord of the Flies" hierarchy that is created is dead on in my opinion.He points out that prison wardens primary duties are to keep the prisoners in one place, feed them, and keep them from killing each other. The school principal's job in many cases is only a small step up from that because the job is to keep the kids in one place, feed them, and keep them from killing each other and to attempt to provide some level of education at the same time.
Computer Art
I found the second essay equally compelling. Graham talks at length about how the world sees computer programming as a "science" when it is in fact more of an art. They compare programmers to physicists and mathematicians while Graham claims they are better compared with painters and other artists.Common "wisdom" on computer programming suggests that the program should be well thought out and planned before the first line of code is typed. Graham suggests that programming is more of a living creation that is sketched and then fleshed out over time and that it takes on new life as it evolves to the final product.
Web-based Applications
A few of the essays revolve around Graham's start-up Viaweb. Viaweb was one of the first, if not THE first application service providers (ASP) because their product worked entirely off of their servers and was accessed via the web (hence the name Viaweb) by its customers.The essays about the thinking behind this set up and why Graham feels that the web-based approach will eventually beat out the concept of installing software on each and every desktop computer are insightful and thought-provoking.
Programming With Lisp
Graham devotes a few essays to the programming language Lisp and why they chose it as the basis for creating the code for Viaweb. He talks about its pros and compares it with other languages as well as explaining why he feels using Lisp gave them a competitive advantage in the marketplace.