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Motley Fool Hidden Gems Investing

The Pitfalls of Selling Stocks (and How to Avoid Them)

Motley Fool Hidden Gems Investing

The Motley Fool

Business, Investing

4.33.1K Ratings

🗓️ 25 November 2025

⏱️ 19 minutes

🧾️ Download transcript

Summary

Some of the biggest mistakes investors make aren’t the stocks they buy - they’re the ones they sell. In today’s episode of Motley Fool Money, host Emily Flippen is joined by Fool analysts Jason Hall and Jeff Santoro to look back at some of The Motley Fool’s most painful sell decisions, from Netflix and beyond. They dig into: Why selling is so emotionally tempting and is often the biggest mistake for retail investors How a single 5, 10, or 100-bagger can offset other losers How to build a framework to help investors hold onto winners without holding everything forever Companies discussed: NFLX, SE, FLSR, CMG, GRMN, RCL, MELI, ISRG, TGT, WMT Host: Emily Flippen, Jason Hall, Jeff SantoroProducer: Anand ChokkaveluEngineer: Bart Shannon Disclosure: Advertisements are sponsored content and provided for informational purposes only. The Motley Fool and its affiliates (collectively, “TMF”) do not endorse, recommend, or verify the accuracy or completeness of the statements made within advertisements. TMF is not involved in the offer, sale, or solicitation of any securities advertised herein and makes no representations regarding the suitability, or risks associated with any investment opportunity presented. Investors should conduct their own due diligence and consult with legal, tax, and financial advisors before making any investment decisions. TMF assumes no responsibility for any losses or damages arising from this advertisement. Learn more about your ad choices. Visit  ⁠megaphone.fm/adchoices Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

Some of the biggest mistakes investors make aren't the stocks they buy. They're the ones they sell.

0:09.4

We're reflecting on past selling missteps today on Motley Fool Money.

0:18.3

It's Tuesday, November 25th. Welcome to Motley Full Money. I'm your host, Emily Flippen, and today I'm

0:23.6

joined by Fool analyst Jason Hall and Jess Santoro to discuss one of the most dangerous things

0:28.3

investors can do, selling good companies too soon. Today, we're going to be looking back at some

0:33.7

of the rule breaker and stock advisor recommendations that we sold that went on to become

0:37.9

five, ten, and even a hundred baggers to hopefully help you, our listeners, build a healthier

0:43.0

mindset around when to sell, when not to, and why buy and hold investing still usually

0:48.1

wins out. Jason, I want to start big picture here. If you look back at many of our full scorecards,

0:53.4

we've had some amazing winners and of course some absolutely brutal mistakes. And many of these mistakes, in my opinion, the worst ones are the ones that we sell, right? What is it about selling that is so emotionally tempting to investors, even those like us, that claim to be very long term? So as investors, like we try to be high-minded, we have these financial goals, long-term

1:13.0

and short-term that we're trying to reach.

1:14.9

But we're also humans, and humans are messy.

1:17.2

We're just not wired to really be good at investing.

1:21.0

Fear and greed are exceptionally strong emotions.

1:23.9

We search for confirmation bias.

1:26.5

And there's always a data point that feeds what you want to

1:29.8

believe to be true, whether it's actually the right thing to act on or not. If we own a great

1:35.2

stock or maybe we just get lucky and we buy a stock and it doubles, those old tropes start to

1:42.3

sound smart. It's house money. I'm going to lock in my profits now if we own

1:47.3

a stock that falls in value again this is like that meat sack part of us in our brain that we don't

1:54.8

really always understand that we have to fight against the value of a stock going down hurts

2:00.2

more than a stock going up feels good.

...

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