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Read it after finishing the more talked about book, “The Black Swan”. 

And more than once caught myself thinking that “Fooled by Randomness” and “The Black Swan” were two integral parts of one quite big unbearably boring volume, seriously lacking in substance and structure. 
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This is the best book I have read all year, closely followed by his other book, The Black Swan. Fooled by Randomness is one of that select group of books that changes your mind entirely. Once I read it I could never look at the world the same again, nor could I take my old assumptions for granted.

We are so accustomed to looking at the world and seeing patterns that we do not always understand that we may be seeing randomness and imposing a pattern where none belongs. Taleb talks about the various ways we fool ourselves and why we cannot help but be wrong much of the time. He branches out from probability and mathematics to explain why our minds work as they do and what the recent psychological and neuroscientific studies as well as evolutionary psychology have to say about how we think and why we are so easily fooled by randomness.

His writing is lively and peppered with anecdotes. It is an easy read but he never condescends to the reader nor dumbs down the subject. A great read!
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While Nassim Taleb presents some thought-provoking ideas, he is overly vague and pretentious. He spends much of the book pointing out how much smarter he is than other people, but shares little wisdom and even fewer specific strategies.
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1) Most of Taleb's examples come from finance and financial markets. The heavy focus on financial markets is both a strength and a limitation. From a strength perspective, Taleb has deep personal experience in finance, particularly in risk management, which makes his insights grounded in real-world practice. The market is also a rich environment for discussing randomness and uncertainty — with so many unpredictable factors at play, it’s an ideal domain for illustrating how randomness manifests. However, for a reader without a background in finance, this focus can feel alienating, and that’s valid. Taleb does a decent job of breaking things down, but for a broader audience, more relatable examples could have made his points resonate more.

A book which I think has a slightly different perspective and does a slightly better job of balancing broader examples in randomness and chaos is Brian Klaas’s Fluke. It’s a great example of how randomness can be explored through a wider lens, and many readers who prefer a broader approach (more chaos theory and less finance) might find that more accessible. Taleb’s book is definitely steeped in that particular world, so it’s not unusual that someone might feel that it’s a bit one-dimensional. Taleb’s later works (especially Antifragile) takes a broader perspective and may speak to the broader applicability of his ideas.

2) Taleb’s take on determinism (or lack thereof) is definitely one of the more complex and less explored aspects of the book. Taleb is a big proponent of randomness and the non-deterministic nature of the world, which plays into his larger philosophy on risk, uncertainty, and unpredictability. However, the topic is touched on in passing without much elaboration. For someone already familiar with deterministic models of the universe (as in the works of Brian Klaas or Robert Sapolsky), Taleb’s occasional nod to non-determinism can feel underdeveloped.

Taleb does flirt with philosophical issues, but his focus tends to be on the practical implications of randomness in everyday life and markets, not necessarily on metaphysical debates. In a sense, his philosophical musings on determinism feel like a tangent that might have benefitted from more context or explanation. Taleb’s Antifragile might provide a little more clarity on his views regarding chaos and determinism, though he doesn’t fully resolve these issues in either book.

3) Malcom Gladwell and Taleb have some similarities in their exploration of the unexpected effects of randomness and chance on our lives, but their approaches are quite different. Gladwell is more narrative-driven and accessible, often telling stories that feel emotionally resonant, while Taleb is more analytical, grounded in philosophy and probability theory. In comparison, Gladwell's work is more digestible for the average reader, while Taleb’s can sometimes feel like a series of abstract points stacked upon each other.

Despite Taleb’s approach being more technical, it's easy to find value in his analysis. This shows that his book can appeal to people from different backgrounds, even if it's not as smooth or entertaining as a Gladwell narrative. It’s one of those books that rewards perseverance because the ideas can be quite revelatory once you get past the initial difficulty.

It’s also worth noting that Freakonomics and David and Goliath are both excellent in showing how things like chance, context, and perceived disadvantage can be turned to one’s advantage, which overlaps with a lot of the core messages in Fooled by Randomness. Gladwell’s style, which leans on anecdotes and compelling storytelling, may make his points easier to digest, while Taleb’s dense, essay-like format requires a more intellectual engagement, but both are talking about the same kinds of phenomena. It's easy to appreciate the overlap in these authors, even though the presentation differs.