When To Sell a Stock
Earn Your Leisure
iHeartPodcasts
4.9 • 7.9K Ratings
🗓️ 23 February 2026
⏱️ 4 minutes
🧾️ Download transcript
Summary
Sell a long term position when one of these is true:
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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.
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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.
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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.
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Permanent capital loss risk is rising. Too much debt, weak balance sheet, dilution, shrinking market, or “hope” is the strategy.
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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.
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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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Transcript
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| 0:00.0 | Okay, let's get into the, when should someone sell a long-term position? |
| 0:06.1 | I think this is a great question. And you have two types of investors, the investor you're |
| 0:13.1 | trying to get the capital together to get to your first goal. And then you may have the second |
| 0:19.0 | investor that's hit a couple of different targets. |
| 0:22.4 | But my thing is, if you have not hit whatever your freedom number is |
| 0:25.9 | and shots to the brother for this question, there's no reason to sell. |
| 0:29.6 | The way that the market is going with in terms of inflation. |
| 0:33.8 | Just over the weekend, like I was on a plane coming back, right? |
| 0:40.4 | U.S. debt will reach reach 64 trillion by 2036 doubling from 2023 um i know that we'll talk about the Dow piqued at 50,000 even though |
| 0:49.5 | there's all kind of unrest in the world um debt's GDP some it may hit two or 300, and that may be the baseline or |
| 0:57.5 | median number for most countries going forward. |
| 1:01.1 | So my thought is if you sell off your assets too early, unless you've hit your end goal |
| 1:07.0 | number where you like your FU number, you're going to need more capital in the future. |
| 1:12.0 | And I don't see on either side, Republican or Democrat, a great potential leader in sight. |
| 1:18.4 | So I wouldn't hold off and think, well, I have more than enough money right now. |
| 1:23.2 | It would be a mistake. |
| 1:24.7 | So if the debt is supposed to increase by that much by 2036, the value of the |
| 1:30.5 | dollar is going to drop even more. Ray Dalai will just put out this past weekend. We're in phase |
| 1:34.1 | six of the New World Order. So now it's not the time unless you've gotten to that mark of |
| 1:42.8 | $20,000, $ million, 30 million, 50, |
| 1:46.0 | or that other number that we talk about behind the scenes. Now is not the time to sell or liquidate. |
| 1:51.0 | And I think it's important just to pay attention to the positions that you're in because something like PayPal is down 89%. |
... |
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