I am surprised you have never heard of Taleb before. He is quite controversial, but often deeply original and almost never boring. You should read "Antifragile: Things that Gain from Disorder" which imho is his best book. "Black Swan" is more well-known, but I was a slightly disappointed by it.

> I am surprised you have never heard of Taleb before. He is quite controversial, but often deeply original and almost never boring.

Yeah, probably fault due to my own ignorance/bubble in which I live. But I like reading controversial but cleverly put together essays. I like it when someone challenges my own views with a well thought through argument, because that is the best way to either learn something new, or at least learn to understand other people better. So either way I feel like I always walk away as a winner whether I agree or disagree in the end. Thanks for the recommendation!

>But I like reading controversial but cleverly put together essays. I like it when someone challenges my own views with a well thought through argument,

Try Chesterton then. A little old but still relevant. E.g. could try Heretics.

Or Unpopular Essays by Bertrand Russell.

Or almost anything by Orwell; his crankiness knows no limits.

Black Swan was just a simple analogy that the author decided to write an entire book about.

> I am surprised you have never heard of Taleb before.

He's just one of today's "Lucky 10.000"[0]

[0] - https://xkcd.com/1053/

Seinfeld effect RE: Black swan. The ideas have become pretty common place (though most uses of the phrase in the mainstream are incorrect) so they don't seem novel ~15 years later.

And his writing has improved.

Skin in the Game is the example heavy companion/ follow up to the more technical antifragile.

He has written some interesting stuff. In particular, I recommend his book the Black Swan -- it is a very nice description of why there are often structural incentives to disregard unlikely/low-probability events.

But he's also definitely over the hill as a thinker. About the only notable thing he's done in the last few years has been sustaining a long-running and personal feud with Nate Silver (of 538) about who among them better understands probability.

Skin in the game is more recent.

Actually, skin in the game explains his feud with Nate Silver.

I recommend his interviews on Econtalk: https://www.econlib.org/econtalk-by-featured-guest-and-lette...

He has a really good rapport with the host (Russ Roberts) and it seems to tamper down his tendency to rant against the stupidity of others.

Then definately check his twitter, he is quite a figure:

https://twitter.com/nntaleb