Simply keeping pace with peers is not a valid measure of success. If peers are taking excessive risks in a bubble, matching their performance means you were equally foolish. True skill is outperforming in bad times while keeping pace in good times.

In a rising market, the investors taking the most risk generate the highest returns, making them appear brilliant. However, this same aggression ensures they will be hurt the most when the market turns. This dynamic creates a powerful incentive to increase risk-taking, often just before a downturn.

Underperforming VC firms persist because the 7-10+ year feedback loop for returns allows them to raise multiple funds before performance is clear. Additionally, most LPs struggle to distinguish between a manager's true investment skill and market-driven luck.

A long bull market can produce a generation of venture capitalists who have never experienced a downturn. This lack of cyclical perspective leads to flawed investment heuristics, such as ignoring valuation discipline, which are then painfully corrected when the market inevitably turns.

Judging investment skill requires observing performance through both bull and bear markets. A fixed period, like 5 or 10 years, can be misleading if it only captures one type of environment, often rewarding mere risk tolerance rather than genuine ability.

An investor's lived experience can be a poor guide to long-term market realities. For example, someone who started their career after 2009 has only known a US stock market that consistently rewards dip-buying, a pattern not representative of broader history.

The underperformance of active managers in the last decade wasn't just due to the rise of indexing. The historic run of a few mega-cap tech stocks created a market-cap-weighted index that was statistically almost impossible to beat without owning those specific names, leading to lower active share and alpha dispersion.

Timing is more critical than talent. An investor who beat the market by 5% annually from 1960-1980 made less than an investor who underperformed by 5% from 1980-2000. This illustrates how the macro environment and the starting point of an investment journey can have a far greater impact on absolute returns than individual stock-picking skill.

Most investors evaluate performance over a few years, but financial economist Ken French states it's 'crazy' to draw inferences from three, five, or even ten-year periods for an active fund. Shorter timeframes are heavily influenced by randomness and luck, leading to flawed investment decisions.