Nassim Taleb's books are an antidote to many weird founder & startup anxieties

Cross-posting from Reddit. I'm the OP. I got into Nassim Taleb when I picked up Black Swan in a bookstore a year ago. His style is not for everyone, and he definitely thinks he's smarter than most... but man, if his books didn't help me figure out some stuff about startup life. His Incerto series (Fooled by Randomness, Black Swan, AntiFragile, Skin in the Game) hits on the themes of randomness and, specifically, what I think of as "the structure of chaos." The future is fundamentally unpredictable and random in ways that fool even the most intelligent statisticians, forecasters, and entrepreneurs. If I could boil down my biggest learnings from this series, it's this: - Every massively successful startup is fundamentally lucky. They did not strategically optimize every decision to achieve success - they only think they did because of postdictive narrative building. They were fooled by randomness. - If you understand the structure of randomness (specifically, what Taleb calls Mandelbrotian "Black Swan" randomness vs. Gaussian "normal" randomness), then you realize that *someone* has to occupy the long tail positions at the upper and lower distributions - but the people occupying those positions have no more choice in the matter than you or I do. - You can do all the correct things and still fail. In fact, this is the most likely outcome by far. But if this is true, then it relieves a ton of the pressure that comes with trying to optimize every decision and minute of your day, all the time. We still have agency. We can still materially impact our customers and the direction of the business, but it's more a question of exposure: how do I limit my downside risk to acceptable levels while exposing myself to as much upside as possible? Everything else will happen as it happens. However, this DOES mean we can quit listening to gurus, reading business help books written by MBAs, or listening to endless podcasts from entrepreneurs and VCs with survivorship bias (I'm guilty - having done all these things). Every startup will succeed or fail in its own unique, unpredictable, and completely inimitable way.