What Are You Actually Putting In There?

Ten o'clock on a Tuesday night. I've got a contract that needs sorting before morning — customer details, dates, dollar figures, a couple of lines even my own lawyer hasn't seen yet. All typed up and ready to go.

Cursor blinking in the AI chat window. A short cut to getting the work done. Finger over the button. I paste it in...

Not because I didn't think about it. I did — for about three seconds. Long enough to register that I was about to hand over a live contract, details, names and numbers attached, to a company on the other side of the world that I know nothing about, that I've never met, and that could do whatever it likes with it after I hit send. Then I hit send, because it was ten o'clock and doing it by hand would've taken another hour I didn't have.

Has that ever happened to you? You know exactly what you're handing over, and to who you can't actually say. You do it anyway, because it's late and you just want the thing sorted.

I've watched other owners do exactly the same thing, dozens of times now. Nobody skips that moment of knowing. Everybody overrides it anyway.

The Trade Nobody Names

Here's the choice you're actually making, whether you've said it out loud or not.

Option one: you re-explain your business to the AI every single time. Who your clients are, how your margins work, what happened with that supplier last year, why this particular contract clause matters more than it looks like it should. Every session. Forever. It's exhausting, and it's exhausting in a way that never shows up on an invoice, so nobody budgets for it.

Option two: you stop re-explaining, and you feed it instead — your client list, your financials, the redundancy conversation you haven't had yet — into a system that isn't yours, that you don't control, and that you've never actually read the terms of.

Most owners I talk to are doing a bit of both, badly, and feeling slightly sick about it the whole time. And, a lot of the time their staff are doing it without them even knowing it!

That queasy little pause before you hit send? That's not paranoia. That's you doing the maths on a Tuesday night — and the maths always comes out the same way: finish the job now, worry about it later.

The Crown Jewels

The thing worth protecting in your business isn't the AI model. It's your private data. The client relationships, the judgement you've earned the hard way. It's the one thing nobody else can get their hands on. Lose it and you've lost what makes you different.

And yet we spent a year identifying the crown jewels and the next year pasting them into other people's systems, one chat window at a time.

I don't say that to make anyone feel stupid. I've done it plenty. Financials I wouldn't hand to a stranger at a barbecue, typed straight into a box owned by a company on the other side of the world, because it was late and I wanted to go home.

Where Does It Actually Go?

Real question — sit with it for a second. When you pasted that last thing in, where did it actually go? Who can see it? How long does it sit there?

Most owners don't know. Most days, neither do I.

And to be clear — this isn't a "cancel your subscriptions, AI is dangerous" piece. I'm not that guy, and if I ever become that guy, someone needs to take my keyboard away. I use these tools constantly and they've earned their keep.

This isn't about trust in the tool. It's about noticing that every AI product built for small business right now works the same way — you send it your stuff, and it lives on their machine, not yours. Nobody built it that way to catch you out. It's just the only version anyone's built so far. Doesn't mean it's the only one there is.

The Question Worth Actually Answering

So here's the one I'd sit with, and it's uncomfortable.

What's the most valuable thing in your business — the thing that would actually hurt to lose, or hurt to have leaked — and where does it currently live?

For a lot of owners, the honest answer is: scattered across six months of chat histories, in a system they didn't choose carefully, said yes to in about four seconds flat, on a night they just wanted the job done.

That's worth twenty minutes of thought. Not because you should stop using these tools tomorrow — you shouldn't, the trade-off runs the other way for most of what you do. But knowing which trade you're making, on purpose, is a different thing entirely from doing it by accident every time.

Right, last thing before I go - this is the mess I'm in the middle of sorting out with a few clients right now. I don't have any neat answer yet, so I'll keep you up to date as I go.

So here's where you can help me. If you've landed on your own rule for this, or some trick or approach — please let me know. I'd love to know what's actually working out there, because together we can sort this out.

Good luck out there. And don't forget to have fun!