Combat indecision and emotional attachment by pre-committing to sell an investment if it fails to meet a specific metric (the state) by a specific deadline (the date). This creates a pre-commitment contract that closes long feedback loops and prevents complacency with underperforming assets.

To avoid emotional, performance-chasing mistakes, write down your selling criteria in advance and intentionally exclude recent performance from the list. This forces a focus on more rational reasons, such as a broken investment thesis, manager changes, excessive fees, or shifting personal goals, thereby preventing reactionary decisions based on market noise.

A market enters a bubble when its price, in real terms, exceeds its long-term trend by two standard deviations. Historically, this signals a period of further gains, but these "in-bubble" profits are almost always given back in the subsequent crash, making it a predictable trap.

To pursue massive upside, one must first survive. Gardner mitigates risk by never allocating more than 5% of his portfolio to any new position. This discipline prevents catastrophic losses from a single bad idea, ensuring he stays in the game long enough for the big winners to emerge.

When a small, speculative investment like crypto appreciates massively, it can unbalance an entire portfolio by becoming an oversized allocation. This 'good problem' forces investors to systematically sell the high-performing asset to manage risk, even as it continues to grow.

To combat the emotional burden of binary sell-or-hold decisions, use the "Go Havsies" method. Instead of selling a full position, sell half. This simple algorithm diversifies potential outcomes—you benefit if it rises and are protected if it falls—which significantly reduces the psychological pain of regret from making the "wrong" choice.

In frothy markets with multi-billion dollar valuations, a key learned behavior from 2021 is for VCs to sell 10-20% of their stake during a large funding round. This provides early liquidity and distributions (DPI) to LPs, who are grateful for the cash back, and de-risks the fund's position.

This maxim from legendary value investor Jean-Marie Evillard encapsulates the discipline required during a bubble. It prioritizes capital preservation over asset gathering, accepting the painful short-term business risk of client redemptions in order to protect remaining investors from a devastating market crash.

Rather than passively holding a stock, the "buy and optimize" strategy involves actively managing its weighting in a portfolio. As a stock becomes more expensive relative to its intrinsic value, the position is trimmed, and when it gets cheaper, it is increased, creating an additional layer of return.