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The speaker emphasizes the significance of holding onto your winners, using the example of a company, Expell, that experienced rapid growth and increased in value. He believes in not trimming a position simply because it becomes a large percentage of your portfolio. Instead, he suggests keeping winners in your lineup as long as they continue to perform, similar to having a star player on an ice hockey team. Only when a winner starts to lose its edge does it make sense to reduce the position.