I think anyone who calls Tim Ferriss vapid will have to revisit their opinion from the 4 hour workweek book days. His podcast is one of the most insightful I've found, the questions are incredibly penetrating and detailed. He asks questions in a way that I have not really heard of before from other interviewers, ie "Given circumstances A, and B, and that we could consider or discount C here as well, how would you do X?"

I will also note that in 4HWW that he does tell you to delegate and automate only when you've fully understood what to do. And what's wrong with such automation? That's what we programmers do on a daily basis.