Effective decision-making is not about being right all the time; it's about speed and discipline. Top traders are correct only about 55% of the time. Their real skill lies in quickly recognizing the 45% of wrong decisions and cutting their losses without ego. This principle applies to all leadership.

Investor Victor Orlovski writes 10-15 pages of notes when he passes on a company, compared to only 5-6 pages for an investment. This disciplined reflection on "anti-portfolio" decisions allows him to analyze his reasoning, identify biases, and improve his investment judgment over time.

Sun Tzu's "Art of War" is largely written in the negative ("don't do this"), a "via negativa" approach. This simplifies decision-making by focusing on eliminating obvious errors. In investing, this translates to using checklists of past failures to avoid ruin, ensuring that what remains is the only viable path to take.

Advice from successful people is inherently flawed because it ignores the role of luck and timing. A more accurate approach is to study failures—the metaphorical planes that didn't return. Understanding why most people *don't* succeed provides a more robust framework for navigating risk than simply copying a survivor's path.

When evaluating others' success, ask if their strategy would work for most people who adopt it, or if it relied heavily on luck. If a strategy isn't reproducible and leaves many casualties behind, it's not a model to be learned from, regardless of the impressive outlier outcome.

Disagreeing with Peter Thiel, Josh Wolf argues that studying people who made willful mistakes is more valuable than studying success stories. Analyzing failures provides a clear catalog of what to avoid, offering a more practical and robust learning framework based on inversion.

After a startup fails or you exit, dedicate time to writing a detailed, private postmortem. Critically analyze interactions, decisions, and outcomes. This exercise helps transform painful experiences into a concrete set of operating principles for your next venture.

Before committing capital, professional investors rigorously challenge their own assumptions. They actively ask, "If I'm wrong, why?" This process of stress-testing an idea helps avoid costly mistakes and strengthens the final thesis.

To avoid emotional decision-making, especially with losing positions, write down the specific criteria for any investment. Then, backtest those rules against historical data. This replaces emotional struggle with a systematic, data-driven process.