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When speculative market cycles lift early-stage asset valuations regardless of revenue, investors frequently confuse momentum with skill and believe they are playing with house money. Greg Fleming highlights that the critical filter when evaluating fund managers is whether they have lived through complete market downturns. Managers who have seen cycles collapse retain disciplined risk management, whereas single-cycle operators frequently overplay their hands.

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In a bull market, it's hard to tell if a GP is skilled or just lucky. A downturn reveals their true discipline regarding valuations, capital deployment speed, and how they support founders through down rounds, providing LPs with robust underwriting data.

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.

During periods of intense market euphoria, investors with experience of past downturns are at a disadvantage. Their knowledge of how bubbles burst makes them cautious, causing them to underperform those who have only seen markets rebound, reinforcing a dangerous cycle of overconfidence.

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.

Beyond a strong thesis, Limited Partners (LPs) critically evaluate how crypto fund managers understand and adapt to crypto's four-year bull/bear cycles. A manager's ability to strategically time the market—knowing when to be aggressive versus when to take profits—is a key filter for LPs allocating capital in the space.

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.

A staggering 70% of private credit managers have less than a decade of experience, meaning their entire careers have been in a low-rate, bull market environment. This lack of cycle-tested experience poses a significant systemic risk as market conditions normalize and stress appears.

Many micro-VC funds raised during the 2021 peak are struggling because they deployed all capital in a short 18-month window at peak valuations. This lack of "time diversification"—spreading investments across market cycles—means their entire portfolio is underwater, leading to poor returns and difficulty raising new funds.