Note Phil hasn't been in the corporate world himself. He struck it rich with a dot.com in the 1990s boom and worked on several interesting projects since. Among them was photo website, a Thiel-like coders academy, and flying. He has had one of the first and longest running blogs of my fellow MIT students about tech, business, travel, flying and politics.
I took Phil's class (6.171 - Web Development Lab) in college. It was a ridiculous experience, regularly had to put 40hrs/week just on this class and I'm not exaggerating.
Story time: As part of the class we were working with real clients to develop a web project for them. One day during class, he talked to us about the "technical sidekick", typically a friend of the client's that is somewhat technical and is behind-the-scenes advising the client and typically contradicting all your architectular choices as a developer. Well, to noone's surprise, a few weeks later, our client rolled into a meeting all of a sudden knowledgable as to why .NET was inferior, SQL Server bad, etc. We later found out that he took the time outside class, to take the client out for dinner and act like an adversarial technical sidekick just to teach us that lesson. I was pissed off at the time but now deeply appreciate that lesson
Could you share any lessons he taught you about how to properly deal with the "technical sidekick"? I often encounter them in web consulting and I'm curious to see what Phil's advice on the topic was.
