What he says about missed opportunities, and working for idiotic management, that's the big thing here. You work your ass off, the management does dumb things, so the thing you're working on never really pays off, in money or fun.
The fact that his sister has 10x the assets is kind of an insult after injury kind of thing.
Its important for management to understand the difficulties and decisions made by a development team to properly create a roadmap for the business. I think the author is expressing that the lack of respect for the programmers opinions can be detrimental.
IMO it is essential in today's world to have competent engineering management in the room whenever any major product decisions are made.
The problem that really bugs me as well as a lot of others is perhaps more deep-seated - that the popular kids from high school really do win anyway and become your bosses, and stories like Steve Wozniak or Bill Gates where smart, technical people can get ahead of the incompetent but very personable charlatans are becoming less and less common. That confidence / arrogance really are enough to succeed (many do work hard but so do the majority of technical workers too with almost none of the rewards) in the eyes of US society is a lingering thought.