Jeff Aronson warns that prolonged success breeds dangerous overconfidence. When an investor is on a hot streak and feels they can do no wrong, their perception of risk becomes warped. This psychological shift, where they think "I must be good," is precisely when underlying risk is escalating, not diminishing.

True investment prowess isn't complex strategies; it's emotional discipline. Citing Napoleon, the ability to simply do the average thing—like not panic selling—when everyone else is losing their mind is what defines top-tier performance. Behavioral fortitude during a crisis is the ultimate financial advantage.

As a highly volatile and retail-driven asset, Bitcoin serves as a leading indicator for investor risk appetite. It's a "canary in the coal mine" where a "risk on" sentiment leads to sharp increases, while a "risk off" mood triggers rapid declines, often preceding moves in traditional markets.

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.

Institutions must manage four primary risks: failing to meet liabilities (shortfall), path-of-return volatility (drawdown), access to capital (liquidity), and the reputational risk of underperforming peers, which Matt Bank calls “embarrassment risk.” This last one is often the most delicate and hard to quantify.

Investment risk should be assessed using a 2x2 matrix plotting financial capacity against psychological risk tolerance. A high ability but low willingness is 'defensive,' while a low ability but high willingness is 'naive' and foolish, as it courts consequences the plan cannot survive.

Conventional definitions of risk, like volatility, are flawed. True risk is an event you did not anticipate that forces you to abandon your strategy at a bad time. Foreseeable events, like a 50% market crash, are not risks but rather expected parts of the market cycle that a robust strategy should be built to withstand.

Contrary to popular belief, the 1929 crash wasn't an instantaneous event. It took a full year for public confidence to erode and for the new reality to set in. This illustrates that markets can absorb financial shocks, but they cannot withstand a sustained, spiraling loss of confidence.

During profound economic instability, the winning strategy isn't chasing the highest returns, but rather avoiding catastrophic loss. The greatest risks are not missed upside, but holding only cash as inflation erodes its value or relying solely on a paycheck.