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

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November 25, 2025 • 19 mins

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

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.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}The Pitfalls of Selling Stocks (and How to Avoid Them)