This will be a breeze for Mat. Whatever you may think of him he clearly does make an effort to learn some of the technical analysis stuff so a bit of philosophy will be a walk in the park. And in my view he does have a nihilistic streak!
It takes IMHO about 3 years to get this experience, no crash course is possible.
I see a lot of TA posts here done by noobs.
I personally do not make any TA but I can read TA and evaluate the noobs here
I do think Mat can be too bearish and cynical - if Bitcoin does continue to evolve healthily then I would certainly say that this cynicism got in the way of his understanding and trusting the long-term fundamentals - but I recognise that he has put more effort into learning TA while on these forums and while thinking about Bitcoin than me and quite a few others.