Writing
Essays
Long-form thinking at the intersection of AI, business decisions, stoicism, and ADHD. One model per essay, taken to the bottom — including where it breaks.
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MBA · STO
Invert, always invert: the founder's cheapest edge
Munger borrowed a rule from a 19th-century mathematician. Used well, it is the highest-leverage, lowest-cost thinking tool a founder has — and it fails in three specific ways.
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AI · MBA
What Gartner's 28% actually says
One survey, two denominators: 28% of use cases and 77% of firms. A methodological teardown of the AI-failure statistics before you quote one.
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AI · MBA
Too much, too fast: the mechanics of expectation inflation
Where sponsor pressure comes from, why hype, escalation, and the planning fallacy inflate it, and the written contract that disarms it before a project starts.
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AI · MBA
ROI doesn't live in the model
Swap the model for a smarter one and the number rarely moves. A Theory-of-Constraints reading of why AI value lives in the process — and when the model really is the bottleneck.
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AI · MBA
Pilot purgatory: where AI projects go to die
The average organisation scraps 46% of its AI proofs-of-concept before production, and Gartner forecast 30% of GenAI abandoned after PoC. Why the pilot is built so it cannot cross — and the four design moves that let it.
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AI · MBA
95, 80, 28: the war of AI failure numbers
AI failure statistics are a publishing genre with its own economy. Every producer of a number has a business model, and the choice of methodology decides the result before any data is collected. How to build your own reference class instead of quoting someone else's.
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AI · MBA
AI-ready data is a power problem
Data readiness looks like engineering — pipelines, catalogues, quality dashboards. For most projects that die there, the constraint is property: who owns the data, whose budget pays for its quality, and whose position weakens when it flows.
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AI · MBA
The agent demotions will start after the incidents
A forecast, not a finding — and the diagnosis under it is worth more than the number. Governance built as a two-position switch has no rung to retreat to, so the first incident costs the whole ladder.
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AI · MBA
The company brain and the knowledge nobody wrote down
Vendors sell a system that holds everything your organisation knows. Hayek's knowledge problem, Walsh and Ungson's retention bins and the first benchmark on company-internal data mark the boundary — together with the field experiment that argues against me.
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AI · MBA
The bot rejected everything important without a deadline
A triage rule that welded importance to urgency threw out everything important and slow. Simon on the unit of attention, Leroy on the debt, and eighty-four measured items from two of my own systems.
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AI · MBA
Mainframe and the boundary of GenAI competence
A Gartner forecast about mainframe exits is really a clean experiment on where a model's competence ends. Circle of competence, Chesterton's fence and Hyrum's Law, applied to forty-year-old COBOL — and to the vendor pitch on your desk.
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STO · MBA
Antifragility: how to stand on the right side of volatility
Some systems break under stress, some resist it, some gain from it. Taleb's triad and the barbell, with a founder's allocation worked out in hours — and three honest objections.
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MBA · STO
Via negativa: the discipline of subtraction
The firmest knowledge you hold is negative, so removal is a safer default than addition. Iatrogenics, Lindy, the additive bias — and a calendar audit that returns 18 percent of scheduled time.
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MBA · ∩
Mimetic desire: why you want what others want
Most goals feel self-authored; Girard's triangle says they are borrowed. Careers, rivalry, feeds — and a scorecard audit that shows whose desire sits in your spreadsheet.
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ADHD
Flow has a spec sheet — and hyperfocus does not meet it
Csikszentmihalyi measured optimal experience with pagers: three conditions and a channel between anxiety and boredom. What a founder can engineer — and why hyperfocus fails the spec.
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ADHD · AI
Your brain is a prediction machine — and that reframes ADHD
Predictive coding recasts attention as precision and ADHD as a miscalibrated loop, not weak will — and turns the fix into environment design.
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STO · AI
When machines do the execution, taste is the job
As AI collapses the cost of execution, judgment becomes the scarce, defensible thing. Rick Rubin is the proof — and the cautionary tale.
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MBA
First principles: a real lever with a real bill
A genuine tool that occasionally buys a decade of edge, and expensive enough that misusing it is how smart people reinvent the wheel.
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MBA · ∩
Naval's formula for wealth — and the base rate it hides
Specific knowledge plus permissionless leverage is the solo builder's best hand. The insight is real; the survivorship bias behind it is too.
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AI · ∩
Cognitive sovereignty: choosing whose model of the world runs in your head
Feeds optimise for engagement, LLMs supply default frames. Owning your attention is a deliberate choice — and it can curdle into a self-made bubble.
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ADHD · ∩
Engineer the identity, not the willpower
Behaviour flows from identity, not willpower — which reframes everything for an ADHD-shaped mind. And a rigidly built identity becomes a cage.
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MBA
Your company is a tribe — design the rituals on purpose
Anthropology makes the familiar strange: culture is a system of meaning you're already building. Onboarding is a rite of passage — until "we're a family" becomes exploitation.
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ADHD · ∩
Mismatch: why a Stone Age brain keeps sabotaging a modern life
Ancient drives firing at modern supernormal targets. A design tool for founders and ADHD alike — and a field that earns its bad reputation.
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STO
Stoicism is an operating system for uncertainty — not a mug quote
Dichotomy of control, premeditatio malorum, amor fati — a working system for judgment under uncertainty. And the counterfeit sold as strength.
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STO · ∩
Houellebecq's warning: you can win the game and still have nothing
The dark mirror the optimisation canon needs: a life maximised for freedom can be stripped of meaning. Diagnosis worth taking — prescription worth refusing.
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ADHD
Deep work for an ADHD brain: blocks, or sprints?
Newport's insight is right; the monastic block is built for a neurotypical brain. Hyperfocus sprints may fit ADHD better — with honest caveats.
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STO · ADHD
Solitude is a skill, and you have to build the room for it
Not loneliness — the chosen state where original thought happens. For a founder-parent it must be architected. Over-sold, it becomes isolation.
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MBA
"And then what?" — the two words that separate good decisions from clever ones
First-order effects are obvious; second-order effects arrive late and reverse them. The discipline that catches self-inflicted wounds in pricing and growth.
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STO · ∩
The cat is an accidental stoic, and it has something to teach the founder
Indifference to approval, presence, not chasing — Stoic virtue a cat never studied. A temperament worth borrowing, and why you can't become one.
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MBA · ∩
Stop fighting symptoms: the structure is the problem
Recurring problems are your system working as built. Change the structure, not the symptom — and know when to grab the bucket first anyway.
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Writing is thinking: the case for long formats in a short world
You don't know what you think until you write it at length. The essay forces coherence; long horizons are where compounding lives — with the traps of depth named.
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STO · MBA
Not everything that counts can be counted — but "meaning over metrics" is a dangerous excuse too
Goodhart's law kills dashboard-driven companies; "meaning over metrics" is the phrase founders use to dodge accountability. Telling a good metric from one that ate the goal.
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You are playing a status game right now — the only question is which one
Most behaviour is status-seeking in disguise: dominance, virtue, success. Seeing the game lets you choose a better one — and "I've opted out" is the highest-status move.
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STO · ∩
The second life: what changes when you actually believe you get only one
Finitude is the only honest priority filter. The "two lives" maxim, memento mori, regret minimisation — and why "live each day as your last" is bad advice.