
The Eval That Never Finishes
Why confidence, not capability, is what deep AI products compete on. A first-person look at two-sided drift, rented models, and the measurement you actually own.
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This is where long-form thinking lives: practical essays on strategy, prioritization, and how strong PM leaders improve over time.
Tagged “product strategy”

Why confidence, not capability, is what deep AI products compete on. A first-person look at two-sided drift, rented models, and the measurement you actually own.
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MCP isn't a technical detail—it's a strategic decision about whether your AI product can evolve independently of your model vendor. Here's how to think about it.
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Speed and feature parity are the trap. The moat moves toward embedded domain knowledge and workflow depth before foundation models commodify the gap.
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Retention looks fine—DAU up, sessions steady—but users do their real thinking in ChatGPT and Claude, not your product. Here's what that split means.
Read articleMost PMs think AI means more strategy time. It's the opposite: the gap between PMs who talk product and those who ship is widening fast.
Read articleYou promote your best PM to director and lose the one person who actually ships. The Director Trap—and how to avoid it.
Read articleYour product team just shipped a new AI feature. Forty-eight hours later, OpenAI shipped a better model. Who won?
Read articleA practical breakdown of why generic assistants produce fragile product advice, and how to ground AI decisions with frameworks, criteria, and failure patterns.
Read article13 articles — new essays publish here as the library grows.
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