Theses 09 / 20 AGAINST published 05 Apr 2026 · updated 05 June 2026 · v29

Microsoft Has Lost the Plot

Microsoft's strategic position is deteriorating despite surface-level AI investment. They lack internal frontier models and depend on entity/openai, which is itself strategically unfocused — the Forbes "OpenAI Graveyard" documents deals and products that never materialised, while Anthropic's focus on a smaller number of things continues to pay off. Copilot has "Product Market Failure" (John's phrase). The entity/microsoft integration of Anthropic into Copilot Cowork confirms

+18.8pp
Basket vs S&P 500since published — the verdict number
Basket absolute+34.4% · 1 instrument
S&P 500 same period+15.6%
Call directionBearish ↓

A bearish call is scored on performance relative to the market, not the raw tape.

InstrumentPriceTodaySince publishedvs SPY90d
MSFTMicrosoft 501.02 -1.2% +34.4% +18.8pp
SPYS&P 500 — benchmark 761.78 -0.7% +15.6%
Basket: Single-name thesis

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When we're wrong

2 theses are currently moving against us — Microsoft Has Lost the Plot, +34.4% since published; The SaaS Apocalypse, +54.7% since published. They stay on the board. We update priors on evidence, not on evidence we went looking for.