Nassim Taleb the author though I really can't get into, and to be fair he's had so much success that this is probably my fault.
If you want to get the most out of his work then read his medium blog. Most of his pieces are written in easily digestible formats.
I've re-started trying to read the Black Swan about 10 times and IMHO if you just read the first 3 chapters then you'll get about 95% of what you would if you had read the entire book.
I think the problem with his books that I have is that he considers himself not just an author but a modern day philosopher, and with that comes a level of rigor in his writing that brings me back to my measure theory and real analysis courses.
If you really want to read his books, then start backwards.
Antifragile is awesome, but still very wordy, and builds on top of all his other works. It almost seems to be the culmination of the idea's he's been writing about since the black Swan.
As a side note, for anyone who wants to learn about options trading with a focus on how a trader would view them, ie from a mathematical perspective, then check out one of his first books...... Dynamic Hedging of Options.
http://ca.wiley.com/WileyCDA/WileyTitle/productCd-0471152803...
As a second side note........
His latest concept of “Skin in the game” is the best form of risk control that we've found for reigning in traders. Once traders are required to
1) keep the vast majority of their bonus in the fund for a few years
2) take part of their bonus in the form of non liquid securities if they want to hold more than a certain percentage of their portfolio in non liquid assets
we have found they pay alot more attention to the liquidity of their portfolio and the long term profitability of their portfolio, both of which are good for the long term success of the fund.