One of his investment philosophies that resonates, was his focus on concentrated portfolios. He firmly believed that the more stocks you hold in your portfolio and the more you diversify, the more your performance is likely to be average. Simpson challenged the notion that diversification alone guarantees success, arguing that diluting investments across many stocks could limit the impact of high-performing assets on overall portfolio returns. He questioned the wisdom of investing in multiple mediocre ideas when focusing on a few exceptional opportunities could yield more significant results.

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