Latest essay · 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.

A context window is advertised the way a fuel tank is advertised, in units of capacity, and billed the way fuel is billed, in units consumed. One million tokens is the headline figure on three vendors' pages this month. It is a ceiling, not an allowance. Nothing inside it is included, and on two of the three pages the price per unit changes once a request climbs past a line drawn inside the window. We read the Claude API pricing page, the OpenAI API pricing page and the Gemini API pricing page on October 14, 2026. This essay is about the three separate ways that headline number turns into money, and about a fourth that moves the number underneath you.

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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.

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.

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Article · 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…

AI Coding Assistants · October 14, 2026

GitHub Copilot: The coding assistant most teams already have a login for, repriced in…

GitHub Copilot is the coding assistant for a company that would rather extend a vendor relationship than start one. This is a documentation …

AI Coding Assistants · October 13, 2026

Cursor: An editor built around the agent rather than the keystroke, sold on a…

Cursor is the coding tool for a team that has already decided the agent is the product and the editor is its cockpit. This is a documentatio…

AI Assistants · October 12, 2026

ChatGPT: The assistant most small companies already have, whose real price is…

ChatGPT is the assistant a small company is most likely to already be paying for, often several times over on personal cards. This is a docu…

AI Assistants · October 12, 2026

Claude: An assistant whose pricing page is unusually frank about limits, sold…

Claude is the assistant for a small company that would rather know the rules than be told there are none. This is a documentation review: ev…

Guide · October 12, 2026

A primer on AI assistant pricing for small teams

Our top pick for a small team buying its first AI assistant is ChatGPT Business, because its free tier lets you trial the habit before payin…

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