Drawing from Sun Tzu and Charlie Munger, the key to long-term investment success is not brilliance in stock picking, but systematically avoiding common causes of failure. By identifying and steering clear of ruinous risks like excessive debt, leverage, and options, an investor is already in a superior position.

Investor Peter Lynch's advice highlights that trying to anticipate downturns often leads to missed gains, which can be more costly than the losses from the downturns themselves. The best strategy is often to stay invested rather than waiting on the sidelines for a crash that is impossible to predict.

When an asset sees a massive price surge, it's effectively a "price compression" that pulls years of expected returns into a short period. This raises the probability of future volatility or stagnant performance, as the future gains have already been realized.

During profound economic instability, the winning strategy isn't chasing the highest returns, but rather avoiding catastrophic loss. The greatest risks are not missed upside, but holding only cash as inflation erodes its value or relying solely on a paycheck.

Howard Marks argues that you cannot maintain a risk-on posture and then opportunistically switch to a defensive one just before a downturn. Effective risk management requires that defense be an integral, permanent component of every investment decision, ensuring resilience during bad times.

This maxim from legendary value investor Jean-Marie Evillard encapsulates the discipline required during a bubble. It prioritizes capital preservation over asset gathering, accepting the painful short-term business risk of client redemptions in order to protect remaining investors from a devastating market crash.

Contrary to the retail investor's focus on high-yield funds, the 'smart money' first ensures the safety of their capital. They allocate the majority of their portfolio (50-70%) to secure assets, protecting their core fortune before taking calculated risks with the remainder.

A 50% portfolio loss requires a 100% gain just to break even. The wealthy use low-volatility strategies to protect against massive downturns. By experiencing smaller losses (e.g., -10% vs. -40%), their portfolios recover faster and compound more effectively over the long term.

When asset valuations are elevated across all major markets, traditional fundamental analysis becomes less predictive of short-term price movements. Investors should instead focus on macro drivers of liquidity, such as foreign exchange rates, cross-border flows, and interest rates.