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Sleep Well Portfolio - AI Risk Assessment

Can AI create and then run a replica of our 12 businesses? Which one is most at risk or most insulated? Result: I am trimming one and adding to two.

Trung Nguyen @SWI's avatar
Trung Nguyen @SWI
Feb 27, 2026
∙ Paid

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Hi sleep well investors,

As long-term owners, I get excited when there are indiscriminate sell-offs. This is when good deals are found. Last year, I conducted a tariff risk review across all holdings and, as a result, cut MIPS from the portfolio.

This time, I see a lot of AI-related disruptions across all businesses. And with the rapidly changing context, I need to act quickly and decisively. I found one in which one of twelve holdings is highly disrupted (a Sell candidate) and two that require close observation; the rest are highly insulated.

AI risk assessment

Before we dig into the analysis, I’ll present the framework and the context.

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