The creator regrets not selling Consolidation Software when it was up significantly, as it has since fallen back, illustrating the risk of not trimming positions.
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Should you sell your winners?
Dividend GuyMar 15, 2026
The creator discusses when to sell winning stocks, emphasizing holding onto them as long as the investment thesis remains valid and the company's financial metrics (dividend triangle) are strong. He advises against rebalancing by selling winners to buy losers, instead suggesting a personal portfolio weight limit (e.g., 10%) to trim positions that become too large, not out of fear, but to manage risk and prevent overexposure.
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The creator has held Apple since 2014, highlighting its long-term growth potential and significant total returns, reinforcing the strategy of holding winners.
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