The primary investment risk is permanent loss, not price fluctuation. Volatility becomes a tangible risk only due to external factors like an investor's psychology, career pressures, or institutional needs (e.g., daily fund withdrawals, university budget draws).

Scott Barbie's value fund experienced a massive drawdown before a 91% rally. This illustrates that systems with high variability show the strongest regression to the mean. If your investment theses are sound, a period of severe underperformance can be a leading indicator of a powerful recovery.

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.

The primary driver of market fluctuations is the dramatic shift in attitudes toward risk. In good times, investors become risk-tolerant and chase gains ('Risk is my friend'). In bad times, risk aversion dominates ('Get me out at any price'). This emotional pendulum causes security prices to fluctuate far more than their underlying intrinsic values.

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.

A 50% portfolio loss requires a 100% gain just to break even. The wealthy use low-volatility strategies to protect against massive downturns. By experiencing smaller losses (e.g., -10% vs. -40%), their portfolios recover faster and compound more effectively over the long term.

Contrary to expectations, drawdowns in managed futures frequently occur when equity markets are performing well. The strategy's recovery periods, however, often coincide with equity market turbulence, highlighting its counter-cyclical nature and making it behaviorally difficult to hold.