Reflections from the engine room.
The essays here are working drafts of the arguments I make on stage, in advisory rooms, and inside the company I run. Some of them have become talks. Some of them are still wrong in ways I haven't found yet. If you spot one of those, tell me.
The Map Is Not the Terrain
The penicillin allergy on page seven that had never been tested, the discharge letter that read clean but wasn't, and what happens when AI extracts data from documents that were already wrong. A lesson learned at twenty in a forest at night, applied to clinical AI in 2026.
Read essay →Founder Mode Has a New Floor
Brian Chesky has been talking about founder mode again. The advice founders are given — hire great people, get out of the way, free yourself for the strategic work — is the advice that nearly broke Airbnb. What changes when AI removes most of the excuse for not staying close to the work.
Read essay →Why Interdisciplinary Teams Keep Arriving at Obvious Answers
A 1985 experiment showed that groups discuss what they share, not what they know — and quietly erase the diversity they were assembled to combine. The fix has been known for forty years. Almost nobody does it. What changes now that the cost has finally collapsed.
Read essay →More essays
I Finally Have an Executive Coach Again. It's an LLM.
A year of using AI for feedback on myself — what I missed in meetings, where I rationalise, what I confuse with progress — and the three-part framework I arrived at: an initial deep-dive, a weekly Sunday session, and a daily check-in. The prompt is in the piece.
Read essay →AI Was Supposed to Give Us Time Back. Instead, It Made Us Work More.
An eight-month HBR study inside a 200-person tech company found AI did not reduce work; it intensified it. Why the expansion feels like growth. Why the conventional advice — "set boundaries, protect your time" — is not wrong, just insufficient. What it actually demands.
Read essay →If you want new essays first. I post the kernel of every essay on LinkedIn before it arrives here.
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