Writing on Technology Leadership & AI Strategy
Essays on technology leadership, AI adoption, and software strategy.
New Motor, Old Belts
Cheap software does not redesign a firm. The mills only changed shape because the buildings wore out, and software never wears out. Until the old thing is cheap to throw away, you are bolting a new motor onto old belts.
Nobody Gets Fired
Every founder believes the better product wins. In business-to-business it does not, and the reason is not that buyers are stupid. They are answering a different question from the one you are pitching. On the uncertainty tax, the safe incumbent, and why the challenger wins not by proving superiority but by making the change short enough to survive.
The Memory That Won't Compress
The vendors say agent memory is solved - extract the facts, embed them, retrieve on demand. But the institutional memory that actually stops an agent repeating your worst mistake is felt history, and felt history resists embedding by construction.
4HWW Was Right — We Just Needed Better Agents
Tim Ferriss was right that most of your work can be automated — and wrong about what you would do with the freed time. On agents, the anti-hustle case, and the half of the job that was always the point.
Agents Give You Cadence
The conventional sell of AI agents is intelligence, or speed. The thing they actually give you, for the kind of business I run, is cadence. Reliable, repeatable, undistracted rhythm. The boring half of work finally has a home.
The Non-Anxious CTO
Every AI-for-CTOs piece in 2026 is about managing anxiety. The work I keep coming back to is older. Edwin Friedman, writing thirty years ago, told leaders to be the non-anxious presence in their systems. The infrastructure question turns out to be the embodied form.
The Memory You Own
The second brain was a personal knowledge system for humans to browse. Version two has to be built for machines to query - and most of us are building it as a feature inside someone else's platform, which turns out to be the most insidious lock-in yet.
The Sum of All Tokens
AI lets you replace paid software with custom tools that fit your problem. But the cost shifts to tokens plus human insight — and insight is the scarce half.
The Clean Interface
A weekend of AI-assisted home energy optimisation revealed the inversion: the sophisticated parts of software are robust now; the simple parts are fragile.
The Long Obedience
Why staying in one place for fifteen years turned out to be a competitive advantage - and what happens when AI meets patience.
Fifteen Years of sheepCRM
How a favour for a friend became a membership CRM serving over a hundred organisations. The sheepCRM story — from Access replacement to focused product.
The End of Simplicity
When AI collapses the cost of building features and agents replace human users, what happens to our instinct for simplicity? On abundance and discipline.
The Spreadsheet Moment
AI code generation is doing for software what VisiCalc did for financial modelling — putting creation into the hands of people who understand problems.
The Three Mountains
A simple model for operational maturity — where you actually are, not where you think you are. From a primary school framework to a decade of consulting.
The Accidental Operating System
Holacracy was criticised as too rigid for humans. It might have been building the organisational architecture AI agents need.