Stefan has some amazing content and a huge knowledge about history. I just wish he wasn't so obsessed with hyping every alpha guy (including Trump) and with his belief (yes it' s a belief) that somehow the true free market solves all the society's problems better than any alternatives. I love this guy, but sometimes I also hate when I see him not being able to look past his own blind spots.
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I agree, his economics is a bit dogmatic and fairly unsophisticated. If you haven't read the Global Minotaur I think you might like it (primarily because it's really good).
I don't think he's pro Trump at all. He simply points out that a lot of people dislike him because of the wrong reasons. His intention is to get people used to questioning the status quo.