Where your context files live

Every Context setup produces files. Markdown that holds your decisions, your voice, the way your company actually works. They compound. Six months in, they’re worth more than the day we wrote them.

One rule never moves. Those files live in accounts you own. Day one. Yours to keep if you ever walk away. I don’t host your setup inside my own subscription or some platform I run for you, the way a lot of AI consultants do. Your knowledge shouldn’t sit behind a login that isn’t yours.

That feels convenient right up until you want to leave, or the consultant disappears, or the tool shuts down. So I settle ownership first, every time. What’s left is a smaller question: which account?

Here’s how I actually think about it.

Google Drive: start with what you have

Most founders are already in Google Workspace. If you are, this is the easy answer. Your personal context sits in your own Drive. Company context goes in a Shared Drive we both work from. The Shared Drive earns its place: it keeps company knowledge attached to the company instead of one person’s login. People come and go, the files stay.

The caveat I owe you: Google can read these files, and Google is a US company. For most early-stage work that risk is theoretical. If you handle regulated or legally sensitive material, read on.

OneDrive: the same answer for Microsoft companies

If your company runs on Microsoft 365, and in Finland plenty do, the shape is identical. Your personal context lives in your own OneDrive. Company context goes in a SharePoint document library, which is what Teams files are underneath. Same logic as the Shared Drive: the library belongs to the company, not to anyone’s login.

Same caveat as Google: US company, Microsoft holds the keys. And one practical note. The Mac sync client is the weakest part of the stack, and the folders need to be set to always keep on this device, or the files turn into placeholders that tools can’t read.

Tresorit: when privacy is a real requirement

Tresorit is a Swiss company, files encrypted on your machine before anything leaves it. Even Tresorit can’t read them. You own the account, I get invited to one folder. It costs more and the ecosystem is smaller, but for sensitive work that’s the right trade.

Proton Drive: one encrypted home

If you already live in Proton, or you want files, mail, and calendar under one encrypted roof, Proton Drive fits. Same Swiss privacy footing as Tresorit. The desktop sync is younger, so I treat it as the pick for people bought into the wider Proton stack rather than a pure file-sync choice.

Nextcloud: your own server, more work

For the rare client who wants to run their own thing, Nextcloud hosted in the EU means nobody but you touches the files. More setup, more maintenance, nobody to call when it breaks. Right for regulated industries. Overkill for a two-person startup.

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The short version: start with the suite you already pay for, Google or Microsoft, and move later if the stakes change. These are markdown files. Migrating them is an afternoon, not a project. Pick whatever fits how you already work. The only thing that has to stay true is that the files belong to you.