When To Sell a Stock

When To Sell a Stock

Author: iHeartPodcasts February 23, 2026 Duration: 3:26

Sell a long term position when one of these is true:

 

  • You already hit your “freedom number.” If the goal is reached and you are locking in lifestyle security, reducing risk, or shifting into more stable assets, selling can make sense.

  • The fundamentals broke, not just the price. Revenue model changes, margins deteriorate, leadership issues, regulation, or the company loses its edge. If the business is no longer what you originally bought, it is not a “hold,” it is a new decision.

  • They lost their moat and fell out of the top tier. If they are no longer one or two in the space, and competitors are clearly winning, that is a real reason to exit.

  • Permanent capital loss risk is rising. Too much debt, weak balance sheet, dilution, shrinking market, or “hope” is the strategy.

  • Risk rules were violated. If you use a stop-loss or max drawdown rule (example: 25%), you follow it. A long term timeframe is not an excuse to ignore risk management.

  • Opportunity cost is too high. Even if it might recover, your money could work harder elsewhere in a stronger business or better trend.

 

 

In short: Do not sell just because you are scared or because the headlines are loud. Sell when the goal is met, the thesis changes, the moat is gone, or risk management demands it.

 

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Hosted by Rashad Bilal and Troy Millings, Earn Your Leisure pulls back the curtain on the financial mechanics that power the worlds of sports and entertainment. This isn't just about headlines; it's a deep dive into the real stories of how money moves and how deals are made. You'll hear candid conversations that dissect business models and unpack the journeys of entrepreneurs, providing a street-smart education you won't find in a standard textbook. Each episode feels like a vital seminar, blending sharp analysis of current financial trends with the relatable context of pop culture. The Earn Your Leisure podcast, from iHeartPodcasts, operates on a simple premise: true financial freedom comes from understanding the game behind the game. It’s for anyone ready to look past the glamour and learn the practical strategies that build lasting wealth. Tune in for straightforward talk that makes complex business concepts accessible, always grounded in real-world examples from the industries that shape our culture.
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