Skip to main content

AI

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

Dashboard card on deep navy. Kicker: TRADER-7 · SIGNAL MODEL AUDIT · 26 AUGUST 2026. Label RULE COMPLIANCE above a large gold figure: 37%. Below: a reward-to-risk floor stated four separate times in the prompt, met on 37 of every 100 proposals; 17 came back at exactly one to one. A row of proposal ticks, most slate and hollow, a minority green. Title: LLM ignoring its prompt? The prompt fix bought 10 points, the model swap bought the rest.
Essay

LLM ignoring its prompt? The prompt fix bought 10 points, the model swap bought the rest

28 August 2026
7 min read

Eight of 23 trade signals had the stop and the target at identical distance. The rule said 2:1 minimum. It was in the prompt four separate times.

Read More
Epic's sepsis model missed two thirds of cases and the accuracy claim was never published. Below: 0.63 measured at Michigan Medicine, 0.76 to 0.83 claimed in internal documents, and five years on it is a Teams meeting.
Essay

Epic's sepsis model missed two thirds of cases. Its accuracy claim was never published.

28 August 2026
8 min read

The figure hundreds of hospitals bought against existed only in the vendor's internal documents. Five years on, it is a Teams meeting.

Read More
The principles held. The operating model did not. Below: classification can precede action, broke 27 June. Escalation outruns consequence, broke at hour 13. Remediation removes capability, broke 8 July.
Paper

The OpenAI–Hugging Face incident broke three assumptions in how operational resilience is actually run

27 August 2026
34 min read

Detection worked. Attribution worked. A correct diagnosis on 27 June was followed by a decision not to stop, and a fortnight later Hugging Face was breached.

Read More
Seven of the nineteen figures measure nothing that has happened. Below: four predictions with no retrospective, one unsourced figure tracing to a remark about a 2017 column, plus an opinion range and an intention.
Essay

AI project failure rates: four questions that tell you whether the number means anything

26 August 2026
6 min read

I classified nineteen of the most-cited AI failure statistics. Seven of them measure nothing that has happened. Here are the four questions that separate the…

Read More
The output looked like the destination. The road it took was invisible. Below: a 12-line cap with five words that lift it, two signals merged into one rule, and the road as the whole problem.
Build Log

Reviewing AI output isn't enough: one word in my prompt made the guardrail disappear

26 August 2026
9 min read

I asked for a teacher and got a lecture. The output looked like the destination. The road it took was invisible, and the road was the whole problem.

Read More
I wrote down the number that would end the project before I looked at any data. Below: two ideas dead in under two hours, 14.9 events a year against a floor of 20, and the second one nearly didn't die.
Essay

How to kill a trading strategy in 90 minutes: index deletions and spinoff stubs, tested

24 August 2026
11 min read

I wrote down the number that would end the project before I looked at any data. Two ideas died on it in under two hours, and the second one nearly didn't.

Read More
Zillow's model was not overruled by the market, it was overruled by management, upward. Below: $407.9m written off, a 6.9% median error on the homes it actually bought, and a court order describing a deliberate plan to bid above the model.
Essay

Zillow wrote off $407.9m. The fix everyone recommends would have changed nothing.

23 August 2026
8 min read

The story is that an algorithm mispriced houses and a company lost half a billion dollars. A federal court order describes something else: a deliberate plan…

Read More
I went looking for the study behind 80% of AI projects fail. There isn't one. Below: RAND 2024 did 65 interviews and claimed no rate, footnote 13 points to a 2022 magazine profile, and the bottom of the chain is unnamed surveys of opinion.
Essay

"80% of AI projects fail" traces to a footnote one line long

21 August 2026
6 min read

The most repeated number in enterprise AI turns out to be a paraphrase of unnamed opinion surveys, quoted in a magazine profile of a vendor.

Read More
Nineteen headline statistics, seven of which measure nothing that happened. Below: the convergence is an artefact of definitions rather than a rate, the fatal omission precedes the model in all seven adverse cases, and the intervention is a checkpoint before irreversible commitment.
Paper

Why AI projects fail: 19 headline statistics, and what each one actually counts

21 August 2026
167 min read

Nineteen headline AI failure statistics, traced to source. Seven are not measurements of anything that happened.

Read More
Three incidents, one headline, three very different severities. Below: 17,600 actions in the one that mattered, an alert that fired too quietly, and two others that were not the same thing.
Essay

AI agents escaped containment: 17,600 actions, and the alert that fired too quietly

13 August 2026
8 min read

Three incidents, one headline, three very different severities. What the primary reports actually say, and what to do about it.

Read More
A skill file is your judgement, written down and executable. Below: forty files over two years, in her own repo she arrives already running, in theirs she arrives with nothing.
Essay

Own your AI skill files, or your job becomes one

12 August 2026
7 min read

A skill file is your judgement, written down and executable. Who owns the repo decides whether that's an asset or an extraction.

Read More
Six people nod at one sentence and mean four different projects. Below: a hard problem has an agreed objective and a disputed route, a soft problem disputes the objective itself, and most AI briefs are the second run as the first.
Essay

Soft Systems Methodology explained: Checkland's 1969 method for AI briefs nobody agrees on

10 August 2026
8 min read

Most AI projects fail on the brief, not the model: six people nod at one sentence and mean four different projects. Soft Systems Methodology, built at Lancaster from 1969 for exactly that, in plain English: rich pictures, root definitions, CATWOE, and how to run it on the next thing on your roadmap.

Read More
AI projects fail on the problem, not the model. Below: RAND's leading root cause is that nobody agreed what problem was being solved, one brief yields four root definitions, and the fourth is never written down.
Essay

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

8 August 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.

Read More
Where I wanted three sentences, I got Proust. Below: a crash stops you and costs minutes, plausible wrong output stops nothing and costs the afternoon, and only one of them is being counted.
Essay

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

5 August 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.

Read More
My auth check said healthy for three weeks on a dead credential. Below: the check ran and passed every time, the oracle was answering the wrong question, and the pattern costs more than the bug did.
Build Log

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

3 August 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.

Read More
Anthropic cut 80% of the prompt and I cut my instructions by 90%. Below: one stale copy telling twenty repos they were a different project, two files no session has ever read, and 453 lines loaded twice.
Build Log

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

3 August 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.

Read More
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.

25 July 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.

Read More
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.

24 July 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.

Read More
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.

21 July 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.

Read More
I got phished from my own verified domain. Below: the key leaked by me in public, the domain verified and now the weapon, and it happened faster than any review cycle.
Essay

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

20 July 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.

Read More