Library

Books, articles, and videos I find myself recommending over and over. If something is on this list, it changed how I think.

Probability & Decision-Making
Superforecasting Philip Tetlock & Dan Gardner Disciplined thinking, probabilistic reasoning, and constant updating can make ordinary people far better at predicting the future than experts working on intuition alone. Fooled by Randomness Nassim Nicholas Taleb On confusing luck with skill, narrative fallacy, and survivorship bias. The book that made me permanently suspicious of any success story that doesn't account for the role of chance. The Psychology of Human Misjudgment Charlie Munger Munger's legendary 1995 speech cataloguing 25 cognitive biases that reliably lead people astray. Less academic than Kahneman, more practical, and delivered with the bluntness only Munger could get away with. Keep Your Identity Small Paul Graham Short and devastating: the things tied to your identity become impossible to reason about. Once you see this pattern you notice it everywhere. Thinking in Bets Annie Duke A former world-champion poker player on separating decision quality from outcome quality. You can make a perfect bet and still lose. The discipline is judging the process, not the result. Why? Magnets Richard Feynman Captures science as an endless chain of explanations that eventually leads to the humility of admitting where understanding ends. A short clip that's stayed with me for years.
Economics & Investing
How the Economic Machine Works Ray Dalio Distills macroeconomics into a clear framework covering credit, debt cycles, and productivity growth. The clearest 30 minutes you can spend on how the global economy actually moves. The Most Important Thing Howard Marks Second-level thinking, risk as something different from volatility, and the importance of being a contrarian who's also right. Marks writes the way the best investors actually think. Poor Charlie's Almanack Charlie Munger The collected wisdom of Munger's talks and letters. The core idea — build a lattice of mental models from multiple disciplines and use them to think through everything — rewired how I approach problems outside of investing too.
Business & Technology
Aggregation Theory Ben Thompson How the internet shifted power from distribution to demand-side economies of scale. Understanding business strategy today requires seeing how platforms aggregate users, data, and attention. Maker's Schedule, Manager's Schedule Paul Graham The tension between creative work that requires long uninterrupted blocks and managerial work built on meetings. A short essay I revisit constantly when scheduling my own time. How the Biggest Consumer Apps Got Their First 1,000 Users Lenny Rachitsky Lenny interviewed dozens of founders to map the actual playbooks behind early growth. Pattern-rich and practical, not the mythologized versions. Technological Revolutions and Financial Capital Carlota Perez The definitive framework for how technology waves create speculative bubbles, then crash, then deploy into the real economy. If you lived through both the dot-com bust and the '08 crisis, this book explains the pattern underneath both. Why Software Is Eating the World Marc Andreessen The 2011 op-ed that became a generation's thesis statement. Every industry would be remade by software. Thirteen years later, it reads less like a prediction and more like a history. Status as a Service (StaaS) Eugene Wei Why social networks succeed or fail, mapped on status and utility axes. Long, brilliant, and deeply systematic. The best piece I've read on how incentives shape platform behavior.
Systems & Incentives
Sapiens Yuval Noah Harari Weaves history, anthropology, and psychology into a story about how shared myths and collective imagination shaped human civilization. Changed how I think about why humans cooperate at scale. Thinking in Systems Donella Meadows The clearest primer on feedback loops, leverage points, and unintended consequences. If you've ever wondered why well-intentioned policies backfire, start here. Governing the Commons Elinor Ostrom The Nobel Prize-winning rebuttal to Hardin. Communities can and do self-organize to manage shared resources without privatization or top-down regulation. The empirical counterweight to elegant theory. The Death and Life of Great American Cities Jane Jacobs The original argument for emergent order over central planning. Jacobs saw what the urban planners couldn't: that messy, mixed-use streets are safer, more productive, and more alive than anything designed from above. Scott's "Seeing Like a State" builds directly on her work. Freakonomics Steven Levitt & Stephen Dubner The book that made incentive design mainstream. Cheating sumo wrestlers, real estate agents who game their own clients, crack dealers who live with their moms. Every chapter is a case study in how incentives produce unexpected behavior. The Tragedy of the Commons Garrett Hardin The original 1968 articulation of how individual rational behavior destroys shared resources. One of those ideas so foundational it's hard to remember a time before it had a name. Seeing Like a State James C. Scott Why top-down schemes to improve the human condition fail. States simplify complex systems into legible metrics, then optimize for the metric instead of the reality. Goodhart's Law at civilizational scale.