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When to Double Down In Investing

Here is a recent question that I got from a reader:

I have a question for you that I don't think you've addressed in your blog. Do you ever double down on something that has dropped significantly beyond portfolio rule VII's rebalancing requirements and you see no reason to doubt your original thesis? Or do you almost always stick to rule VII? Just curious.

Rebalance the portfolio whenever a stock gets more than 20% away from its target weight. Run a largely equal-weighted portfolio because it is genuinely difficult to tell what idea is the best. Keep about 30-40 names for diversification purposes.

This rule is meant to control arrogance and encourage patience. I learned this lesson the hard way when I was younger, and I would double down on investments that had fallen significantly in value. It was never in hope of getting the whole position back to even, but that the incremental money had better odds of succeeding than other potential uses of the money.

Well, that would be true if your thesis is right, against a market that genuinely does not understand. It...


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