First - background - I've been through most of the political spectrum at one time or another, in search of truth. I've left most of it as well for the same damn reason. One truth I hold close is this: life is not perfect, there is no perfect choice, there is no ideal, failure modes are a constant, and that people are emotional. All of that has to be factored into whatever decision that one tries to make.
The "people are not rational one" was perhaps the hardest to suss out for me, and "failure is constant, good enough is good enough" the most difficult one for me to accept.
So I found the interview fascinating - especially Scott's discussion of systems vs goals - and my immediate thoughts of how that ties into antifragility, especially given his stated position that we are not rational (in many ways he's right). I also found fascinating his recent articles on persuasion in the light of Aristotelean Dialectic vs Rhetoric, and the greater importance in most cases of addressing the emotional state.
While it is often a broken and incomplete rationality – see again the observation that people are generally irrational – you find more of it, more often, in engineering disciplines because those require yes or no answers that are either true or false no matter how you feel. Of course, those people then can sometimes be more, compensatingly, irrational in completely different areas. Often in the belief that people are just as programmable and malleable as electronics. This last has been around since the industrial revolution.
It's interesting that Scott Adams, Eric Raymond, and yes, even Stefan Molyneux in discussions on atheist versus religious people, have now made similar points. Namely: religion in general having a self-governing set of precepts that restricts both the amount of human evil and its scope, as well offering a higher standard to live up to and judge by than "law".
I'll also be commenting more, later, on "systems", and other factors, later. In the meantime, go watch the video.