Sleep Well Portfolio (May 2026) - Software is back? 8% portfolio rebound in a day
Lead by CRWD: up 283% FTNT: up 154% other recent buys bounced. Five losers out of 12 holdings; 8 months of decline coming to an end.
Sleep Well Portfolio consists of time-tested leaders. We screen them using a rigorous checklist and track their theses regularly to determine when to buy. So far, we have made one mistake, and 23 out of 40 transactions have been profitable. All about us here.
Summary of May 2026
The relentless decline in software stocks is showing signs of coming to an end. As of writing, the portfolio is ready to look ‘hot’ again, despite not owning any pure-play AI.
CrowdStrike, the first pick, is now up 282%; Fortinet is up 154%; other software platform picks have also bounced 30%; I am most pleased with the latest pick, no. 24, which is also up 30%. It was arguably a tougher BUY decision given I entered at a 55x FCF valuation, similar to my first CrowdStrike buys.
After 8 months of me ‘looking wrong’, the waiting and slow buying-in are finally showing results. As always, investing is simple but incredibly hard. Discipline and patience are required but cannot be taught; they must be ‘absorbed’ slowly. Everyone will make mistakes, and the last 8 months have not been easy, but failing and going through pain are the only ways to improve as a long-term investor.
Going forward, my approach remains the same. Continue to study and add irreplaceable businesses, patiently waiting for buys at reasonable prices (often at historic lows). I don’t promise monthly/weekly ideas or regular buy/sell signals. I provide only business-focused research; you need to make your own portfolio decisions.
One of the examples is my most recent pick and buy - SWI #24:
SWI #23:
Before we celebrate, recall that the last prolonged decline began with the start of the war in Ukraine around February 2022. It lasted a year and a half for some of our businesses. We are roughly halfway there. The pain may return. But owning the best businesses is the best pain prevention. Their stock rebounded spectacularly between mid-2023 and mid-2025, and this time won’t be different.
Market cycles are a feature of long-term investing, not a bug.
Stay focused on your long-term goals. For me, it’s 2037 (when my daughters will have full control of the Sleep Well Portfolio). I continue to put aside some savings and own more winners - ‘winner keeps winning ’- in both bear and bull markets.
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