McCullough advocates for a "promiscuous" investment strategy, quickly moving capital to where signals are strongest. He argues that emotional attachment to winning positions, or "bag holding," is the primary way investors lose ground. The goal is to compound returns by avoiding drawdowns, not by marrying a single investment thesis.
The "Liking-Loving Tendency" causes investors to identify personally with their holdings. They ignore faults, favor associated things, and distort facts to maintain positive feelings. This emotional attachment leads them to rationalize bad news and hold deteriorating assets for too long, destroying capital.
Some companies execute a 3-5 year plan and then revert to average returns. Others 'win by winning'—their success creates new opportunities and network effects, turning them into decade-long compounders that investors often sell too early.
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.
While long-term focus is a virtue, investment managers at WCM warn it can become an excuse for inaction. During periods of significant market change, blindly "sticking to your knitting" is a liability. Recognizing when to sensibly adapt versus when to stay the course is a critical and nuanced skill.
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.
To decide whether to sell a long-held asset you're attached to, imagine it was sold overnight and the cash is in your account. The question then becomes: "Would you use that cash to buy it back today?" This reframe bypasses status quo bias and the endowment effect, making the correct decision immediately obvious.
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.
To combat emotional decision-making, Eddie Elfenbein’s strategy mandates replacing exactly five of 25 stocks each year. This rigid structure forces patience and prevents impulsive trades, even when he feels tempted to sell a poorly performing stock. This system prioritizes long-term strategy over short-term reactions.
While having a disciplined rule like reviewing a stock after 24 months is useful, it should be subordinate to a more critical rule: sell immediately if the fundamental investment thesis breaks. This flexibility prevents holding onto a losing position simply to adhere to a predefined timeline.
The secret to top-tier long-term results is not achieving the highest returns in any single year. Instead, it's about achieving average returns that can be sustained for an exceptionally long time. This "strategic mediocrity" allows compounding to work its magic, outperforming more volatile strategies over decades.