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AI

Working with AI, building with it, and thinking about where it goes.

Diagram contrasting a straight-line delivery pipeline with a learning cycle that loops back through comparison
Essay

80% of AI projects fail on the problem, not the model: Soft Systems Methodology

August 8, 2026
7 min read

More than 80% of AI projects fail, and RAND's leading root cause is not the technology: nobody agreed what problem was being solved. Soft Systems Methodology, built at Lancaster from 1969 for exactly that failure, gives you a way to surface the disagreement in an afternoon instead of a year.

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A single short instruction beside an enormous wall of text conveying the same thing
Essay

Opus 5 verbosity: where I wanted three sentences, I got Proust

August 6, 2026
8 min read

I judge AI models by how often they make me swear. Opus 5 turned swearing into punctuation, and the reason is more interesting than I first thought.

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A diagram of a monitor whose only reporting path runs through the system it is monitoring, so when that system fails the monitor goes quiet instead of raising an alarm.
Build Log

Why AI checks fail silently: 1,278 restarts behind a healthy status

August 3, 2026
8 min read

My auth check said healthy for three weeks on a dead credential. The pattern behind it costs more than the bug did.

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Diagram: one 709-line CLAUDE.md at the root of a project tree, fanning out to twenty repositories, each receiving the same wrong sentence about being a documentation project with no build system.
Build Log

Anthropic cut 80% of Claude Code's prompt. I cut my CLAUDE.md by 90% the same day.

August 3, 2026
6 min read

An audit of 116 instruction files found one stale copy telling twenty repos they were a different project, two files no session has ever read, and 453 lines loaded twice. Here is what to delete from your own CLAUDE.md, and the method that beats judgement.

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Three status labels feeding a parser: two written as Done and Closed bounce off; one written as Resolved with a date passes through into a report.
Essay

My AI Agents Kept Losing My Work. The Fix Is Older Than Computers.

July 25, 2026
6 min read

Seventeen finished pieces of work were invisible to my own tracking system, and the cause wasn't effort or memory. A Berkeley talk gave me the name for what fixed it: an ontology. Here's the version that fits a one-person company.

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Split panel: a crossed-out offer that says We sell AI solutions, against a highlighted offer that says Your phone gets answered, every call, day and night.
Essay

The Data Said Nobody's Buying AI. Turns Out I Was Selling the Wrong Thing.

July 24, 2026
5 min read

Last week I showed the demand numbers for AI consultancy are dire. This week a veteran operator explained the part I missed: the demand isn't dead, it's mute. Nobody buys AI. They buy outcomes, told concretely enough to defend to a board.

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Conference-thumbnail style graphic: a bordered jamiewatters.work badge, an orange markdown-logo square with the word Markdown, and giant white text reading Go find the customers
Essay

Garry Tan Just Described My Setup. Then I Noticed What He Left Out.

July 21, 2026
7 min read

The YC president gave a talk describing, almost item for item, the AI system I already run. The validation lasted about ten minutes. Then I noticed the word neither of us was saying.

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A padlock icon sitting inside a stream of code, half open, on a dark terminal background
Essay

I Leaked an API Key and It Turned My Own Domain Into a Phishing Weapon

July 21, 2026
6 min read

I got phished from my own verified domain, using an API key I'd leaked myself: what actually leaked, how fast it happened, and what I changed.

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A simple data panel: only 8 to 18 percent of small firms pay for any AI, median spend about $28 a month, and only about 8 percent hire a consultant for AI.
Essay

Everyone's selling AI consultancy. The data says nobody's buying.

July 19, 2026
4 min read

A $1,000-an-hour AI consultancy playbook is doing the rounds. The demand data, and a friend who sells everything except this, disagree.

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Two routes to the same tool: a short straight line labelled 'one goal prompt' and a long looping line labelled 'a full framework', both arriving at a node reading 'same tool, both correct, byte-for-byte'.
Build Log

A goal prompt beat my build framework on a real job

July 16, 2026
5 min read

Same spec, same model, two methods: a seven-part goal prompt against a full agent framework. The lean prompt tied on correctness and won on time, cost, and clutter. Here are the numbers.

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On the left, a lone clamp gripping a single tool; on the right, an organised wall of specialist tools around a small instrument sealed under glass with a wax seal.
Build Log

How to trust AI-written code you didn't read line by line

June 22, 2026
5 min read

AI can write working code in minutes. The hard part is trusting it without reading every line. Here's what actually makes AI-built code trustworthy.

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A craftsman's workbench with hand tools and wood shavings beside a brass measuring gauge sealed under a glass dome with a wax seal
Build Log

Everyone's selling autonomous AI agents. I built one, and the real lesson was 20 years old.

June 21, 2026
4 min read

An AI agent spent an afternoon optimising one of my apps. It tried a change, measured it, kept the one that was genuinely faster, reverted three that weren...

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A reassuring padlock on the front door of a house, while a small side window stands quietly open in the background.
Build Log

I Ran Graphify. The Privacy Trap Is Real, Just Not the One Everyone Warned Me About

June 20, 2026
7 min read

Six AIs told me Graphify uploads your code. I checked by running it, and the actual gotcha is smaller, quieter, and easy to miss.

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A wide-open landscape funnelled into three identical numbered doors, the rest of the terrain greyed out behind them.
Build Log

The Three Options Trap: Why Claude Keeps Killing the Good Bit

June 18, 2026
7 min read

Claude has a habit of collapsing an open conversation into three multiple-choice options, and once you see why it does it, you can stop it doing it to you.

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A row of carved wooden birds beside an open book on a sunlit windowsill
Build Log

I Almost Told You a Lie. Six AIs Handed It to Me, in Unison.

June 17, 2026
7 min read

A field note from researching Graphify: the real privacy model, the honest token numbers, and why I check the source before I publish.

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A small wooden boat in tidal shallows at golden hour, with a stranded larger vessel in the distance
Build Log

Building David, Not a Smaller Goliath

May 11, 2026
13 min read

How a trading agent reveals the game retail can actually win — by playing where the funds can't or won't go, and learning to love the play.

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An XML file full of PLACEHOLDER_X tags, fanned with eleven ghost copies. Caption: × 12 files. None ever filled in.
Build Log

BOS-AI had twelve XML files holding nothing

May 10, 2026
4 min read

I checked the XML files BOS-AI used to store 'institutional memory' for thirty agents. Every tag was PLACEHOLDER_X. So I deleted all twelve.

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Half of agent-11 was scaffolding the platform now provides
Build Log

Half of agent-11 was scaffolding the platform now provides

May 9, 2026
6 min read

I shipped v6 of agent-11 last month. The biggest single change was deletion. The deployed CLAUDE.md went from roughly 250 lines to under 80. The MCP prof...

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A brass and glass hourglass mid-flow on a dark mahogany surface
Build Log

Now the Real Data Starts

May 9, 2026
9 min read

Seven months of building bought me a system that finally tells the truth about itself. The data those seven months produced is mostly unreadable. The clock just started, and not a moment too soon.

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A roulette wheel mid-spin in a dimly lit private gambling room
Build Log

The House Always Wins: Why Retail Crypto Trading Is About to Get a Lot Harder

May 3, 2026
10 min read

Three forces are converging on retail crypto traders, and none of them favour the small player. The edge isn't intelligence anymore. It's owning the table.

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