Naval Ravikant: The Angel Philosopher's Guide to Wealth
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Naval discusses specific knowledge, leverage, and calculated risks in entrepreneurship.
More resources on Risk Taking
Lecture 1 - How to Start a Startup (Sam Altman, Dustin Moskovitz)
Opening lecture of Stanford's CS183B course, in which Sam Altman and Dustin Moskovitz cover why to start a company, choosing an idea and market, building a product people want, and assembling an early team.
Paul Graham Essays
Complete archive of Paul Graham's writing, including the essays on founder mode, doing things that don't scale, and startup ideas that shaped Y Combinator's advice. Argumentative rather than instructional, useful for forming judgment about early-stage decisions.
Against the Gods: The Remarkable Story of Risk
Bernstein traces the history of probability and risk from ancient dice games through Pascal, Bernoulli, Bayes, and modern portfolio theory. Readers come away understanding how measuring uncertainty became possible and where quantitative risk models inherit their assumptions.
hbr.org
Harvard Business Review (hbr.org) offers research-based articles, case studies, and practical guidance on leadership, strategy, and organizational performance for managers and executives.
Antifragile
Taleb's argument that some systems gain from volatility, stress and error while fragile ones break. Introduces optionality, via negativa and barbell strategies, giving readers a heuristic vocabulary for making decisions under uncertainty without forecasting.
Nassim Taleb's Medium/Fooled by Randomness
Nassim Nicholas Taleb's Medium page, where he publishes essays and technical notes extending Fooled by Randomness and Antifragile. Readers learn how fat tails, ruin, skin in the game, and asymmetric payoffs should shape decisions under uncertainty.