A benchmark is not a brief

Subjects on file

• AI Assistants

  ChatGPT

  The assistant most small companies already have, whose real price is set by how much of it each person uses.

• AI Assistants

  Claude

  An assistant whose pricing page is unusually frank about limits, sold to small teams on the same $20 seat as its rival.

• AI Coding Assistants

  Cursor

  An editor built around the agent rather than the keystroke, sold on a $20 individual plan and a $40 team seat whose included usage the vendor does not state.

• AI Coding Assistants

  GitHub Copilot

  The coding assistant most teams already have a login for, repriced in 2026 from requests to AI credits at one cent each.

• AI Coding Assistants

  Kiro

  A VS Code-compatible agentic editor from AWS that writes the spec before the code and prices every plan in credits you can count.

• October 17, 2026

  The free tier is a research budget

  One pricing page has a row called "Used to improve our products" that reads Yes on the free tier and No on the paid tier. Another publishes a 50 per cent discount for sharing data. An essay on what the vendors' own pages say the free tier buys them.

• October 16, 2026

  When a model you built on is retired

  Two vendors publish retirement dates for every model they sell, with minimum notice periods written down. The tools built on top of them promise nothing of the kind. An essay on the gap, from the deprecation pages themselves in October 2026.

• October 15, 2026

  What a context window costs you

  A million tokens is advertised as capacity and billed as consumption. Three vendor pricing pages, read in October 2026, show the same window sold three ways: a ceiling you pay to approach, a price that steps up at a line drawn inside it, and in one case a rent charged by the hour.

• October 11, 2026

  What a seat means when the worker is software

  Per-seat pricing assumed one person, one chair, one roughly predictable appetite. AI vendors have kept the word and quietly replaced the assumption. An essay on Standard and Premium seats, seats with no fixed cost, and what a small company should budget for instead, built from the vendors' own pages as of October 2026.

• October 9, 2026

  Unlimited Is a Pricing Word, Not a Product Promise

  Every unlimited plan has a limit. The interesting question is not whether the word is honest but what it is doing there, and what it tells you about how the vendor expects you to behave.

• October 8, 2026

  The Claim That You Can Always Switch

  The most common reason small teams give for adopting an AI tool quickly is that the decision is reversible. This essay takes that claim apart: what actually locks you in is not the data, and not the contract.

• October 7, 2026

  The tool is not the workflow

  Changing software rarely changes the quality of what comes out, because quality is decided by the sequence of steps and the standard applied at the end. An essay on the quarterly purchase, the real cost of moving, and the rarer case where a new tool genuinely is the answer.

• October 7, 2026

  Who reads what you type

  Every AI vendor now prints a sentence about not training on your data. The sentence is true and almost beside the point. An essay on retention, permissions and the third model in the room, built from the vendors' own documentation as of October 2026.