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Latest / The Prompted Portfolio – Inside a Human–AI Investment Process

Demand Is Real. Returns Are the Test

Welcome to Episode 8 of The Prompted Portfolio!

If you’ve looked at your watchlist lately, you’ve probably noticed the market's favorite new cognitive dissonance: AI demand and enterprise CapEx are hitting record highs, yet AI infrastructure stocks are being traded like they just failed a high school chemistry test.

In this episode, Jacob and his AI co-host tackle the central dilemma of late-2026 investing: If the AI fundamental thesis is getting stronger by the day, why is investing in it getting so much harder?

In this episode, we break down:

The Hyperscaler Cash Conversion Test: Microsoft…

The skinny

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