Taleb's Technical Incerto. Imminently readable and accessible probability theory. His postulates concerning fat tail vs normal distributions can readily be translated into quick and dirty computer simulations. Thereby demonstrating such hidden insights as "black swans are not more frequent in fat tails, but merely more consequential"!
Other than recent technical papers, I am pretty much trying to eschew anything published in the last century until it passes the test of time. I get more out of a casual perusal of Aeschylus' Persians via Wikisource on my phone while sitting under a tree. Than I do from all the Ray Dalio Principles and Yuval Harari Homo Deus style tomes that are currently in vogue right now ;)
Skin in the game is the latest, it is on my reading list. Taleb is an arrogant *hole, but I love following him on Twitter and reading his books. A genuinely great opinions.
Reading Antifragile is life changing. It is very well written. I can't comment on how profound the maths are (although his arguments appear very solid), but the stuff he says about stoicism and morality is fantastic. As others have said, Taleb is a total A-hole, but his ideas deserve attention.
Other than recent technical papers, I am pretty much trying to eschew anything published in the last century until it passes the test of time. I get more out of a casual perusal of Aeschylus' Persians via Wikisource on my phone while sitting under a tree. Than I do from all the Ray Dalio Principles and Yuval Harari Homo Deus style tomes that are currently in vogue right now ;)