Instead of passively holding an investment, view it as an active choice to buy it at its current price every single day. The decision to sell should be based on a clear analysis of the incremental forward rate of return versus deploying that capital elsewhere.

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.

Don't wait until you're completely exhausted to sell your company, as buyers will sense your desperation and gain the advantage. The ideal time to exit is when your passion for the market wanes or growth slows, allowing you to negotiate from a position of strength before burnout sets in.

The optimal exit point for a discretionary trade isn't determined by valuation metrics, but by market psychology. The signal is when investors betting against the trend are experiencing maximum financial and emotional pain, an intuitive skill that cannot be codified into a system.

History shows that markets can remain irrational longer than investors can remain solvent. For instance, the Nasdaq was 40% higher at its post-crash low in 2002 than when media first called the dot-com market "nutty" in 1995. Selling too early, even with sound analysis, often means missing substantial gains.

A practical definition of a bubble is when investor enthusiasm pulls all potential future cash flows and upside into the present-day price. This results in an asset that offers zero forecasted returns over a long period, making it a foolish investment.

Early stages of a bull market are often met with investor negativity and equity sell-offs. This pessimism is a typical part of the behavioral cycle that precedes later-stage optimism and the euphoria which ultimately marks the market's peak. It is a sign that the cycle is not yet over.

Private equity funds, driven by IRR targets and fund lifecycles, often pass up good exit opportunities in hopes of maximizing returns later. This can backfire if the market turns. A better strategy is to sell opportunistically into a rising market, even if it feels early, rather than risk missing the window.

According to investor Howard Marks, people sell assets either because they're up (to lock in gains) or down (out of panic). Both are poor reasons. The only valid reasons to sell are if your original investment thesis is no longer true, or if you've found a demonstrably better opportunity.