I Asked an AI What It Knew About Me. That Is How dearkarl Started

At some point I connected my Gmail and Google Drive to Claude. It was convenient. I could ask it to find an invoice or a booking, and it did.

I didn’t think about it much after that.

Later, out of curiosity, I asked it a simple question: what do you know about me?

The answer

It searched my mail and my Drive, and came back with a summary of my life. It did not even open attachments.

I won’t show it. But here is the kind of thing that was in there:

• Who I am: full name, address, phone number, and where my ID numbers are stored.
• My family: who they are, what they do, their names, their interests.
• My work: where I work, and what has been changing there.
• My home: the property and the paperwork around it, like insurances.
• What I buy, and how I save: from order confirmations and bank notifications.
• What I own and what it’s worth: an insurance policy with every item and its value.
• When I’m away: holiday plans, with dates.
• My health: enough to know it was there.

Most of it came from boring mail. Shipping notifications, booking confirmations, a form from an office.

I wrote the test up properly, with numbers and a made-up example person, on the dearkarl blog.

What made me think

One email on its own was harmless. The problem was putting them together. Two routine messages from different months, read side by side, said something about my life that I had never written down.

Then there were the things that are not facts but access: sign-in links still sitting in the inbox, and a connector that can do more than read.

And it was not only my data. My family, my clients and other people write to me too. None of them agreed to an AI reading their messages.

What I actually needed

When I looked at how I really used the connector, I almost never needed my whole inbox. I needed one email. A flight confirmation, a message from a client, a document someone sent me.

So I gave the AI everything, to use a tiny part of it.

So I built dearkarl

That is the idea behind dearkarl. You forward the emails you choose to a private address, and your next Claude Code session can read them. It never asks for your mailbox. It sees what you sent, and nothing else.

If you have a connector like this, try it:

• Ask your AI what it knows about you. Keep the answer in the chat, don’t save it anywhere.
• Check what the connector can do, not only what it can see. Can it send mail as you?
• Ask yourself how often you need all of it. If the answer is “one email at a time”, share one email at a time.

Stay curious, and a bit careful!