Elite endowments can make financially illogical decisions due to institutional biases. Public pressure on compensation led Harvard to spin out top managers into high-fee external funds, while politically-driven divestment from sectors like oil and gas cost the endowment significant returns.

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When David Swenson published the "Yale Model," many institutions tried to copy it without possessing Yale's resources, network, or manager selection expertise. This led many to chase private equity and hedge funds ill-equipped, resulting in them backing lower-quartile managers and achieving poor results.

Fund managers are like zebras. Those in the middle (owning popular stocks) are safe from predators (getting fired), even if performance is mediocre. Those on the outside (owning unfamiliar stocks) find better grass (higher returns) but risk being the first ones eaten if an idea fails. This creates an institutional imperative to stay with the consensus.

While institutional capital market assumptions align with objective, yield-based models, their actual portfolio actions can deviate. Many institutions, despite models suggesting caution on expensive US stocks, maintained market weight, benefiting from the prolonged bull market. This highlights a critical inconsistency between their stated process and real-world behavior.

Post-mortems of bad investments reveal the cause is never a calculation error but always a psychological bias or emotional trap. Sequoia catalogs ~40 of these, including failing to separate the emotional 'thrill of the chase' from the clinical, objective assessment required for sound decision-making.

The only way ESG investing can effect change is by starving "bad" companies of capital, raising their cost of capital. For the market to clear, non-ESG investors must own those stocks and will only do so if compensated with a higher expected return. Therefore, the ESG portfolio must, by definition, have a lower expected return.

Elite universities with massive endowments and shrinking acceptance rates are betraying their public service mission. By failing to expand enrollment, they function more like exclusive 'hedge funds offering classes' that manufacture scarcity to protect their brand prestige, rather than educational institutions aiming to maximize societal impact.

Great investment ideas are often idiosyncratic and contrary to conventional wisdom. A committee structure, which inherently seeks consensus and avoids career risk, is structurally incapable of approving such unconventional bets. To achieve superior results, talented investors must be freed from bureaucratic constraints that favor conformity.

Superior returns can come from a firm's structure, not just its stock picks. By designing incentive systems and processes that eliminate 'alpha drags'—like short-term pressures, misaligned compensation, and herd behavior—a firm can create a durable, structural competitive advantage that boosts performance.

Top universities with billion-dollar endowments should lose their tax-free status if they fail to grow enrollment. By artificially limiting admissions, they behave like exclusive luxury brands (e.g., "Birkin bags") that cater to the wealthy, rather than fulfilling their mission as engines of social mobility and public service.

Even sophisticated institutional investors exhibit significant behavioral biases. Research on their trades revealed that while their buying decisions added value, their selling decisions were so poor that a random selling strategy would have outperformed their actual sales by 100-200 basis points. They seem to apply discipline to buying but not selling.