As always @andrarchy, really enjoyed your post. Likewise, Taleb is one of my favorite authors; I was lucky enough to get introduced to him and his ideas before I even started my career in finance. as a very junior analyst at a hedge fund, i was tasked to read the black swan and fooled by randomness. never was short vol in any of my portfolio. it has been costly as of the last few years. i don't mind it.
as the concept of antifragility gets more widely known, here is a short video (from jimmy song) of it applied to Bitcoin that I think is quite well done. Was during a conference in LA in Oct 2017. that day, BTC crossed $7,000 and everyone was like celebrating. And now where are we at??
next up on the reading pile is "skin in the game". Will be released on February 27, 2018. cannot wait!
Additional point.
The barbell strategy is a method that attempts to secure the best of both worlds. It’s possible, the thinking goes, to garner substantial payouts without taking on undue risk. The strategy’s prime directive is interesting in that it’s not only counterintuitive to a populace weaned on the benefits of tempering risk and reward, it’s unambiguous: Stay as far from the middle as possible.
Nassim Nicholas Taleb [...] phrases the barbell strategy’s underlying principle as follows:
"If you know that you are vulnerable to prediction errors, and […] accept that most “risk measures” are flawed, then your strategy is to be as hyperconservative and hyperaggressive as you can be instead of being mildly aggressive or conservative."
Source:
https://www.investopedia.com/articles/investing/013114/barbell-investment-strategy.asp#ixzz53AmkiceV
When taking into account potential returns in BTC and crypto in general, one would conclude that the exposure is "hyperaggressive". As a result, it has a place in a portfolio constructed according to the barbell methodology.
Thanks for posting this video! Jimmy Song usually is an insightful guy to hear from.