Many problems have a single "correct" answer (convergent). Investing is different; it's a "divergent" problem where key questions require balancing opposing virtues: concentration vs. diversification, patience vs. urgency. Success lies not in finding a single rule, but in intuitively harmonizing these tensions.
Success requires a paradoxical mindset: commit to a long-term vision (e.g., a decade) while being relentlessly consistent with daily actions. Compounding only works over long time horizons, so outlast competitors by sticking to the process for the 'thousand days' it takes to see exponential growth.
The stock market is a 'hyperobject'—a phenomenon too vast and complex to be fully understood through data alone. Top investors navigate it by blending analysis with deep intuition, honed by recognizing patterns from countless low-fidelity signals, similar to ancient Polynesian navigators.
Most investors cannot excel at both aggressive offense (seeking more winners) and disciplined defense (avoiding losers). These require different mindsets. To build a coherent strategy, one must make a conscious choice about which path to prioritize, as very few possess the skills to master both simultaneously.
Bruce Lee’s philosophy to be “formless, shapeless, like water” is a powerful model for investors. It warns against rigid adherence to a single dogma, like old-school value investing, and instead encourages adapting one's strategy to fit the unique conditions of the current market environment.
In 2008, Howard Marks invested billions with conviction while markets crashed, yet he wasn't certain of the outcome. He held the paradox of needing to act decisively against the crowd while simultaneously accepting the real possibility of being wrong. This mental balance is crucial for high-stakes decisions.
Moving from science to investing requires a critical mindset shift. Science seeks objective, repeatable truths, while investing involves making judgments about an unknowable future. Successful investors must use quantitative models as guides for judgment, not as sources of definitive answers.
Absolute truths are rare in complex systems like markets. A more pragmatic approach is to find guiding principles—like "buy assets for less than they're worth"—that are generally effective over the long term, even if they underperform in specific periods. This framework balances conviction with flexibility.
The sign of a working diversification strategy is having something in your portfolio that you're unhappy with. Chasing winners by selling the laggard is a common mistake that leads to buying high and selling low. The discomfort of holding an underperformer is proof the strategy is functioning as intended, not that it's failing.
The highest-performing strategies often have extreme volatility that causes investors to abandon them at the worst times. Consistency with a 'good enough' strategy that fits your temperament leads to better real-world results than chasing perfection.
Investor Mark Ein argues against sector-specific focus, viewing his broad portfolio (prop tech, sports, etc.) as a key advantage. It enables him to transfer insights and best practices from one industry to another, uncovering opportunities that specialists might miss.