The rule to "Sell the losers and let the winners keep riding" (often phrased as "Cut your losses short and let your profits run") is fundamental to long-term investing success, yet it is one that investors most commonly fail to follow due to behavioral biases.
Here is an elaboration on why this principle is so indisputable, and the psychological pitfalls it helps investors avoid.
The Principle: Sell the Losers and Let the Winners Keep Riding
This principle is about maximizing the benefits of your correct investment decisions and minimizing the damage from your incorrect ones.
1. The Power of Riding the Winners (Gains)
Compounding at Work: The goal of long-term investing is to allow compounding to work its magic. When you sell a winner after a pre-determined, small gain (e.g., selling after a 50% rise), you cut off the exponential growth potential.
The Law of Percentages (Working for You): Once a stock has already doubled or tripled, subsequent small percentage gains translate into massive dollar gains on your original investment. A winning stock only needs to rise by $1\%$ to give you a substantial return on a position that has already grown large.
Quality Pays Off: High-quality companies that are successful often continue to be successful. Selling them prematurely assumes the market has already fully recognized their value, which often isn't true over a multi-year horizon. As the article states, "No one in the history of investing with a 'sell-after-I-have-tripled-my-money' mentality has ever succeeded."
2. The Urgency of Selling the Losers (Losses)
Loss Recovery Math: The math behind losses is brutal. The larger the loss, the greater the percentage gain required just to break even.
A $20\%$ loss requires a $25\%$ gain to break even.
A $50\%$ loss requires a $100\%$ gain to break even.
A $90\%$ loss requires a $900\%$ gain to break even.
Capital Preservation: Selling a loser quickly preserves the remaining capital, allowing you to reallocate that money to an investment with a higher likelihood of generating a profit (i.e., your winners or a new high-conviction idea). Holding onto a hopeless stock ties up capital that could otherwise be working for you.
Avoiding the "Wish and a Prayer": The longer you hold a loser, the more the decision shifts from rational analysis to emotional "wishing and praying" for a rebound. This is not investing; it's gambling.
3. The Psychological Trap: The Disposition Effect
The biggest obstacle to following this rule is a behavioral bias known as the Disposition Effect. This is the tendency of investors to:
Sell Winners Too Early: Driven by pride and risk aversion over gains. Realizing the gain gives an immediate feeling of success, and investors fear that the winner will drop back down before they can "lock in" the profit.
Hold Losers Too Long: Driven by loss aversion and the sunk cost fallacy. Investors feel the pain of a loss twice as strongly as the pleasure of an equal gain. They refuse to sell because realizing the loss means admitting the mistake and closing the mental account at a loss. They hold on, hoping to just "get back to even."
| Behavior | Emotional Driver | Result |
| Sell Winner | Pride, Fear of Regret (Missing out on locking in a gain) | Caps potential profits; limits compounding. |
| Hold Loser | Loss Aversion, Sunk Cost Fallacy (Refusal to admit mistake) | Exposes capital to greater losses; ties up funds for better opportunities. |
4. Practical Implementation
To overcome the emotional biases, implement a disciplined system:
Establish a Stop-Loss (for Losers): Decide before you invest at what point the fundamental thesis is invalidated, and set a maximum loss you are willing to tolerate (e.g., sell if the stock drops $15\%$ or $20\%$).
Define a Rationale for Selling (for Winners): The only acceptable reason to sell a winner is that the company's fundamentals have deteriorated (the original thesis is broken), or you have found a significantly better opportunity (opportunity cost). Do not sell simply because the stock is "up a lot."
Revisit Your Thesis: When a stock falls, revisit your original research. If the company's long-term prospects are unchanged, the dip is a sale. If the core business has fundamentally deteriorated, it's a sell, regardless of how much money you are losing.
This principle is about acting like a cold, rational business owner who cuts failing ventures quickly and generously funds the successful ones, rather than an emotional gambler clinging to past hopes.