Superior long-term returns come from consistency, not chasing top rankings each year. A pension fund that never ranked above the 27th percentile in any single year ended up in the top 4% overall after 14 years. The key is to avoid big losses and let steady compounding win over time.

Investors frequently give up on trend-following strategies after a few flat years, right before they rebound. This is attributed to a deeply ingrained behavioral bias to chase recent performance, which causes them to sell low and miss the subsequent recovery, ensuring they underperform the strategy.

The modern market is driven by short-term incentives, with hedge funds and pod shops trading based on quarterly estimates. This creates volatility and mispricing. An investor who can withstand short-term underperformance and maintain a multi-year view can exploit these structural inefficiencies.

Smith argues that periods of underperformance are an unavoidable feature of any disciplined investment strategy. Rather than panicking and changing course, the correct response is to analyze the cause: was it an execution error, a structural strategy failure, or transient market factors you just have to endure?

AQR's Cliff Asnes highlights that a prolonged period of underperformance is psychologically and professionally more damaging than a sharper, shorter drop. Enduring a multi-year drawdown erodes client confidence and forces painful business decisions, even if the manager's conviction in their strategy remains high.

A Vanguard study of over 2,000 active funds revealed a stark reality: even among the top quartile that survived and outperformed long-term, 95% still lagged their benchmark in at least five years out of the period studied. This proves that frequent underperformance is a normal feature of a winning strategy.

Historical analysis of investors like Ben Graham and Charlie Munger reveals a consistent pattern: significant, multi-year periods of lagging the market are not an anomaly but a necessary part of a successful long-term strategy. This reality demands structuring your firm and mindset for inevitable pain.

Investors rarely sell a fund for outperforming its benchmark too aggressively, but they should consider it. Research by Vanguard's John Bogle tracked the top 20 funds of each decade and found they almost always became significant underperformers in the following decade, demonstrating the danger of chasing past winners.

Even long-term winning funds will likely underperform their benchmarks in about half of all years. A Vanguard study of funds that beat the market over 15 years found 94% of them still underperformed in at least five of those years. This means selling based on a few years of poor returns is a flawed strategy.