A fundamental reason for differing investor behavior is the unit of discussion. Bond investors focus on forward-looking yields, which naturally fosters a contrarian, mean-reverting mindset. Equity investors focus on backward-looking prices and returns, leading them to extrapolate recent trends and chase momentum.

To achieve above-average investment returns, one cannot simply follow the crowd. True alpha comes from contrarian thinking—making investments that conventional wisdom deems wrong. Rubenstein notes the primary barrier is psychological: overcoming the innate human desire to be liked and the fear of being told you're 'stupid' by your peers.

The most profitable periods for trend following occur when market trends extend far beyond what seems rational or fundamentally justified. The strategy is designed to stay disciplined as prices move to levels few can imagine, long after others have exited.

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.

The difficulty in going against conventional wisdom isn't just intellectual. According to David Rubenstein, it's rooted in the human desire to be liked and respected. People avoid contrarian bets because they don't want to be told they're "stupid" by their peers, making the psychological and social cost very high.

Howard Marks offers a crucial corollary to Einstein's famous quote. For investors, the real insanity is failing to recognize a paradigm shift. Applying strategies that worked during 40 years of falling interest rates to the current, different environment is a recipe for failure. The context determines the outcome.

Hetty Green's famous strategy to "buy when things are low" was enabled by two key factors: always having cash on hand and possessing the emotional stability to act decisively when others were panicking. Having liquidity is useless without the courage to deploy it during a crisis, a combination few possess.

Marks emphasizes that he correctly identified the dot-com and subprime mortgage bubbles without being an expert in the underlying assets. His value came from observing the "folly" in investor behavior and the erosion of risk aversion, suggesting market psychology is more critical than domain knowledge for spotting bubbles.

Howard Marks highlights a critical paradox for investors and forecasters: a correct prediction that materializes too late is functionally the same as an incorrect one. This implies that timing is as crucial as the thesis itself, requiring a willingness to look wrong in the short term.