Motley Fool Money Podcast Summary

Episode: The Pitfalls of Selling Stocks (and How to Avoid Them)
Date: November 25, 2025
Host: Emily Flippen
Guests: Jason Hall, Jeff Santoro

Episode Overview

In this thoughtful and practical episode, Emily Flippen is joined by fellow Motley Fool analysts Jason Hall and Jeff Santoro to dissect one of the most enduring sources of investor regret: selling great stocks too early. Drawing on real-world examples from the Motley Fool’s own scorecards—including famous missteps and lessons learned—the team explores the emotional and quantitative pitfalls that lead investors to sell, the rare but powerful math of holding true winners, and frameworks for deciding when selling a stock actually makes sense. With candor and humility, they aim to help listeners build a healthier, more resilient mindset for long-term investing.

Key Discussion Points & Insights

The Emotional Temptation to Sell

• Human psychology vs. best intentions:
  Jason observes that even seasoned analysts struggle with the emotional triggers that cause premature stock sales—primarily fear and greed. Our brains are not wired to be good investors, and the pain of loss powerfully outweighs the pleasure of gains.

  “If we own a great stock … and it doubles, those old tropes start to sound smart. ‘It’s house money, I’m going to lock in my profits.’ ... The value of a stock going down hurts more than a stock going up feels good.” – Jason Hall [01:08]

• Risk tolerance misconceptions:
  Emily highlights how investors (including professionals) often overestimate their own risk tolerance until volatility hits, leading to emotional, hindsight-driven decision-making.
  She provides the example of Motley Fool co-founder David Gardner, who early on sold Netflix—locking in a gain but missing out on life-changing future gains before later correcting the mistake.

  “That initial sale would have resulted in 26,000% gains … making up for any near-term losses.” – Emily Flippen [02:28]

Case Study Regrets: Factoring in Patience and Imagination

• Sea Limited:
  Jeff cites Sea Limited (SE) as a memorable regret, since it was sold for seemingly rational reasons after a period of unprofitability and fierce competition. The stock then delivered over 2,200% in gains, massively outpacing the S&P 500.

  “We sold out of a stock that was going to beat the market … The lesson here is that sometimes, patience pays off. … Sometimes we need to have the conviction to look at the whole business and not just the struggling metrics.” – Jeff Santoro [03:38]

• Expanding on recent losers-turned-winners:
  Emily references a roster of other memorable sales—First Solar, Chipotle, Garmin, Royal Caribbean—all of which soared afterward. Jeff notes that some were reasonable mistakes (limited industry imagination with First Solar in 2012), while in the case of Chipotle, a partial sale (“trim”) proved a better move than a total exit.

  “Sometimes trimming a stock … can let you act on a valuation concern without selling completely out and then missing the rest of the ride. That nuance … paid off.” – Jeff Santoro [07:24]

The Math of Multi-Baggers & Asymmetry in Investing

• One great stock can cancel out a dozen duds:
  Jason lays out why selling potential multi-baggers is so devastating mathematically, even if most other picks go to zero.

  “The most you can lose on a single stock is 100%, while the upside is theoretically unlimited ... If you bought MercadoLibre and 37 other stocks that went to zero, you still would have made money.” – Jason Hall [09:18]

• Market-wide view:
  Emily and Jason both stress that, even in index funds, most gains come from a tiny handful of huge winners.

  “It’s those handful of companies that go on to produce massive returns that result in virtually all of the gains of the stock market.” – Emily Flippen [12:03]

• Personal experience:
  Emily shares her own portfolio’s mixed returns, where a few big winners outweigh a sea of losses.

  “The ones that have done well have more than made up for it.” – Emily Flippen [12:03]

Practical Advice: When Is Selling Actually Justified?

Building a Framework (Not Just Rules)

• Jason’s Framework for Selling:

  • Selling for financial/life-goal reasons (e.g., retirement, planned withdrawal) is a good reason.
  • For other sales, rigorously examine if the issues are business-specific (thesis broken), macro factors (often the worst time to sell), or valuation concerns (especially avoid selling high-growth stocks on valuation alone).
  • Ask: If this stock doubles or quintuples from here, will I regret selling?
  • Enforce a “cooling-off” period of two market days after making a sell decision.

  “A framework helps us build a process that would assist us in making better decisions. … My biggest sell mistakes were for valuation on businesses that can easily grow their revenues 5x or 10x ... It’s almost always best to hold on in those cases.” – Jason Hall [14:30]

• Emily’s Distinction:
  Emphasizes the need to separate price performance from business performance when evaluating sell decisions.

  “Just because the share price has changed doesn’t mean that the business fundamentals have changed.” – Emily Flippen [17:08]

• Jeff’s Friction Tactics:
  Jeff inserts deliberate friction into his own selling process—re-reading financials before making a decision to counter emotional reactions to news or price swings.

  “I force myself to go back and reread the most recent earnings report, the transcript, the press release. … A lot of times that gives me clarity and makes me feel less of the impulse to sell.” – Jeff Santoro [17:56]

Notable Quotes and Memorable Moments

Emotional Reality of Selling

• “We search for confirmation bias and there’s always a data point that feeds what you want to believe ...” – Jason Hall [01:08]

On Top Multi-Baggers Offsetting Many Losses

• “Upside is far greater than the downside ... If you sold out of these companies along the way because of competition concerns, valuation concerns, macro concerns ... you would have missed out on their strong growth.” – Jason Hall [09:18]

The Power of Reflection

• “It’s good to reflect and take some of these lessons. I hope our listeners are able to take these lessons and use them for their own portfolios as well.” – Emily Flippen [18:55]

Important Timestamps

• [01:08] – Why selling is so emotionally tempting for investors
• [02:28] – Netflix sell mistake, early returns vs. long-term opportunity
• [03:38] – Sea Limited: Regret over missed 2,200% gain
• [07:24] – Reviewing a list of “mistake sells” (First Solar, Chipotle, more)
• [09:18] – How one big winner outweighs a string of losers
• [14:30] – Practical frameworks for deciding when to sell
• [17:56] – Incorporating friction and data review to avoid impulse sales
• [18:55] – Final reflections and humility in investing

Tone & Takeaways

The conversation is humble, honest, and focused on practical learning for real investors. The hosts don’t shy away from their own mistakes, but instead analyze them for enduring wisdom. They propose simple, actionable frameworks to avoid emotional mistakes and illustrate, with approachable language and concrete examples, just how powerful long-term holding can be—even for professionals. The overarching message: You’ll probably regret selling that great stock more than you’ll ever regret holding on just a little too long.