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The Journey

Field reports from building with AI in public. What's working, what isn't, and what it cost me. Open numbers, the failures before the wins.

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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 car dashboard where the windscreen is replaced by more dials, illustrating that perception is a model rather than a direct view of the world.
Essay

Bernardo Kastrup's cosmic mind has no plan: what analytic idealism actually claims

August 1, 2026
10 min read

The most rigorous idealist alive gives the non-duality audience far less than they want: a universal consciousness that is instinctive, has no plan, and is not looking back at you. What he actually claims, why he says it cannot be proven, and the one part that survives whoever turns out to be right.

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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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On a Deep Space navy background, a gold-edged card labelled ENCRYPTED REGISTER lists accounts, assets, liabilities and instructions, standing solid in front of three faint dashed cards labelled a service, a vault app and a startup that are fading away. Kicker: DIGITAL ESTATE. Headline: The map is a file. It outlasts every company that might have owned it.
Essay

A friend said it was a business. I decided it was not, and built it anyway.

July 19, 2026
3 min read

A friend said it should be a business. I spent forty years around operations and resilience, so I assessed it honestly, decided it was not, and built it anyway, for free. Here is the reasoning, and why the map of your estate should be a file no company owns.

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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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An ornate, freshly painted facade of a grand house. From the front it looks immaculate. The viewer's angle reveals the back: there is no back. Wooden scaffolding props it up from behind, the timber rotten and warped. The building is a single wall pretending to be a home.
Essay

You Are Not the House You Built

April 26, 2026
4 min read

The third in a series. The performed self is a building you put up because contact with the real one was unbearable. Stopping it from falling down is why you are so tired.

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A 19th-century black-and-white engraving. A robed figure stands on a small stone platform in the middle of a ruined landscape, arms raised in confident declamation. Broken columns lie around him. The platform beneath his feet is crumbling into loose rock and sand, falling away into empty space below — but the figure cannot see this from where he is standing.
Essay

If It Makes You Angry, It Isn't Yours

April 25, 2026
3 min read

Anthony de Mello said you know someone has been brainwashed because they get angry when you challenge their beliefs. Social media and AI have made the condition almost universal.

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Essay

Contact Is the Test

April 18, 2026
4 min read

Self-awareness that doesn't produce contact with other people has gone bad. Dostoevsky figured this out in 1864.

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Essay

Truth Is the Currency of the Future

March 19, 2026
6 min read

I'm betting my family's financial future on truth. Here's why I think you should too.

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