Ep 332: When should you sell an underperforming investment?

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In this episode, Stuart tackles one of the toughest decisions investors face: when to hold onto an underperforming investment and when to cut your losses. While it’s tempting to sell and move on, legendary investor Charlie Munger reminds us, “The big money is not in the buying and the selling, but in the waiting.”

Stuart explores the natural cycles of markets—recovery, expansion, and downturn—and why timing matters. Some investments, like the S&P500 and the Nikkei 225, show that patience often pays off, even after prolonged periods of stagnation. But how do you distinguish between an investment that needs more time and one that’s fundamentally flawed?

He provides practical guidance for reassessing investments, highlighting the importance of revisiting your original decision, understanding opportunity costs, and knowing how to strategically exit when the timing is right. Stuart also shares real-world examples, from property markets to emerging markets, to help listeners make informed decisions.

Whether you’re a seasoned investor or just starting, this episode will equip you with the tools and insights to navigate the complex question of when to hold or sell. Tune in to learn how patience, perspective, and strategy can shape your investment success.

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