When To Sell a Stock

23 Feb 2026 · 3 min · 4 chapters

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In short

Earn Your Leisure Podcast Episode Notes

Episode Title

When To Sell a Stock

Hosts

  • Rashad Bilal
  • Troy Millings

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Episode Overview The episode focuses on critical considerations for selling long-term stock positions. The hosts discuss various scenarios in which investors should consider exiting their investments, emphasizing the importance of strategic decision-making rather than impulsive reactions to market fluctuations.

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Key Points Discussed

When to Sell a Stock The hosts outline specific conditions under which it may be appropriate to sell a long-term investment:

  1. Freedom Number Achieved:
  2. Sell if you've reached your financial independence goal.
  3. This ensures lifestyle security and reduces risk.
  1. Fundamentals Have Broken Down:
  2. If there are significant changes in the company’s revenue model, leadership, or competitive landscape, it may be time to reassess the investment.
  1. Loss of Competitive Advantage:
  2. If a company no longer holds a top position in its industry and has lost its competitive edge, it could be a reason to exit.
  1. Rising Permanent Capital Loss Risk:
  2. Indicators such as high debt, weak balance sheets, and shrinking markets suggest a growing risk of permanent loss.
  1. Violation of Risk Management Rules:
  2. Adhere to stop-loss rules (e.g., a maximum drawdown of 25%). Long-term holdings do not exempt you from risk management.
  1. High Opportunity Cost:
  2. If your capital could be better utilized in a stronger investment, it might be time to sell, even if the current asset has potential for recovery.

Important Takeaway

  • Avoid Emotional Selling:
  • Do not sell stocks simply out of fear or due to sensational headlines.
  • Assess your financial goals, investment thesis, and adherence to risk management.

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Market Insights

  • The hosts discuss various economic indicators and market conditions:
  • U.S. debt projection to reach $64 trillion by 2036, implying potential depreciation of the dollar.
  • Job creation and consumer delinquency rates signal economic weaknesses.
  • Historical trends in debt-to-GDP ratios, emphasizing budgetary concerns for both political parties.

Investment Strategy

  • The importance of being mindful of changing market dynamics and company performance is emphasized. For instance, the dramatic decline in PayPal's stock price underscores the necessity for timely exits based on changing fundamentals, not just market price movements.

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Conclusion

  • The episode underlines the necessity of aligning investment actions with established financial goals and robust risk management strategies.
  • Investors should remain vigilant about market trends and company performance while resisting the urge to react emotionally to short-term market fluctuations.

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Additional Resources

  • Subscribe to the Earn Your Leisure YouTube channel: [Earn Your Leisure Youtube](https://www.youtube.com/@EarnYourLeisure)
  • Join the EYL community for in-depth training: [EYL University](https://www.eyluniversity.com)
  • Invest in the number one stock club: [IAN Invest](https://www.ianinvest.com)
  • Upcoming event: Invest Fest (August 7-9, 2026): [Invest Fest Tickets](https://www.investfest.com)

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Note For further insights and discussions, listeners are encouraged to engage with the hosts and other community members through the provided resources.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Introduction to Stock Selling

1:13 to 1:40

Discussing the question of when to sell a long-term investment.

“Listen to Legally Brunette on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.”

Understanding Investment Goals

1:40 to 3:38

Exploration of the importance of reaching financial goals before selling stocks.

“Charlie's Place, from Atlas Obscura and Visit Myrtle Beach.”

Market Analysis and Investment Risks

3:38 to 4:50

Insights on market trends, debt, and investment risks.

“Now is not the time to sell or liquidate.”

Investment Strategy and Stock Performance

4:50 to 7:18

Advice on managing stocks based on performance and market position.

“i mean real quick job creation is the weakest since 2003 consumer delinquency hit a nine-year high Small cap financials are exposed to both.”
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Transcript

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0:00Johnnie Williams:This is an iHeart podcast. Guaranteed human. Run a business and not thinking about podcasting? Think again. More Americans listen to podcasts than ads supported streaming music from Spotify and Pandora. And as the number one podcaster, iHeart's twice as large as the next two combined. Learn how podcasting can help your business. Call 844-844-iHeart. When segregation was a law, one mysterious black club owner, Charlie Fitzgerald, had his own rules. Segregation in the day, integration at night. It was like stepping in another world. Was he a businessman? A criminal? A hero? Charlie was an example of power.

0:38Johnnie Williams:They had to crush him. Charlie's Place, from Atlas Obscura and Visit Myrtle Beach. Listen to Charlie's Place on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey everyone, it's Emily Simpson and Shane Simpson from the Legally Brunette podcast. Each week we're bringing you true crime through a legal lens. Whether you want all the facts on the disappearance of Nancy Guthrie, or you still need to wrap your head around the ditty verdict, we're breaking it all down step by step. And we're not just lawyers, we're also husband and wife. It makes for some pretty entertaining episodes.

1:13Johnnie Williams:Listen to Legally Brunette on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. When segregation was a law, one mysterious black club owner, Charlie Fitzgerald, had his own rules. Segregation in the day, integration at night. It was like stepping on another world. Was he a businessman? A criminal? A hero? Charlie was an example of power. They had to crush him. Charlie's Place, from Atlas Obscura and Visit Myrtle Beach. Listen to Charlie's Place on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

1:48Rashad Bilal:Okay, let's get into the, um, when should someone sell a long-term position? I think this is a great question. And you have two types of investors. The investor you're trying to get the capital together to get to your first goal. And then you may have the second investor that's hit a couple of different targets. But my thing is, if you have not hit whatever your freedom number is, and shout out to the brother for this question, there's no reason to sell. the way that the market is going with in terms of inflation. Just over the weekend, like I was on a plane coming back, right? U.S. debt will reach$64 trillion by 2036, doubling from 2023.

2:35Rashad Bilal:I know that we'll talk about the Dow peaked at$50 ,000, even though there's all kind of unrest in the world. Debt to GDP, some are saying may hit$200 or$300, and that may be the baseline or median number for most countries going forward. So my thought is if you sell off your assets too early, unless you've hit your end goal number where you like your FU number, you're going to need more capital in the future. And I don't see on either side, Republican or Democrat, a great potential leader in sight. So I wouldn't hold off and think, well, I have more than enough money right now. It would be a mistake.

3:13Rashad Bilal:So if the debt is supposed to increase by that much, by 2036, the value of the dollar is going to drop even more. Ray Dalio just put out this past weekend, we're in phase six of the New World Order. So now is not the time unless you've gotten to that mark of 20 million, 30 million, 50, or that other number that we talk about behind the scenes. Now is not the time to sell or liquidate. And I think it's important just to pay attention to the positions that you're in because something like PayPal is down 89%. So when you start to see that your investments have taken a drastic turn, not just in price, but fundamental changes in the company, fundamental changes in the industry, they no longer have a competitive advantage.

4:02Rashad Bilal:they no longer have a moat there's someone else in the space that is more relevant than them that's performing at a higher level than them I think it's important just because it is if you're not one or two in the industry not to cut you off but if they're not one or two you gotta let it go yeah and you can't like you gotta have a stop loss there too 25 % max 25 % stop loss yeah because like I said PayPal's down 89 % so you can't you can't just say okay i'm just gonna hold it and hope for a miraculous comeback you had a hundred thousand dollars in paypal you know 10 years ago now you got eight thousand dollars like that's not a that's not a recipe to build wealth i mean real quick job creation is the weakest since 2003 consumer delinquency hit a nine-year high Small cap financials are exposed to both.

5:01Rashad Bilal:That's GDP. 20 years ago, it was 60%. It's currently at 145. They're not going to balance the budget anytime soon. No. Not likely. That's why gold got to continue to go up.

5:15Johnnie Williams:When segregation was a law, one mysterious black club owner, Charlie Fitzgerald, had his own rules. Segregation in the day, integration at night. It was like stepping on another world. Was he a businessman, a criminal, a hero? Charlie was an example of power. They had to crush him. Charlie's Place, from Atlas Obscura and Visit Myrtle Beach. Listen to Charlie's Place on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. When segregation was a law, one mysterious Black club owner, Charlie Fitzgerald, had his own rules. Segregation in the day, integration at night. It was like stepping on another world.

5:56Johnnie Williams:Was he a businessman? A criminal? A hero? Charlie was an example of power. They had to crush him. Charlie's Place, from Atlas Obscura and Visit Myrtle Beach. Listen to Charlie's Place on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey everyone, it's Emily Simpson and Shane Simpson from the Legally Brunette podcast. Each week we're bringing you true crime through a legal lens. Whether you want all the facts on the disappearance of Nancy Guthrie, or you still need to wrap your head around the ditty verdict, we're breaking it all down step by step. And we're not just lawyers.

6:34Johnnie Williams:We're also husband and wife. It makes for some pretty entertaining episodes. Listen to Legally Brunette on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. You know Roald Dahl. He thought up Willy Wonka and the BFG. But did you know he was a spy? in the new podcast The Secret World of Roald Dahl I'll tell you that story and much, much more What? You probably won't believe it either Was this before he wrote his stories? It must have been Okay, I don't think that's true I'm telling you I was a spy Listen to The Secret World of Roald Dahl on the iHeartRadio app Apple Podcasts or wherever you get your podcasts This is an iHeart Podcast Guaranteed Human

From the publisher

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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