I pitched my free-automation offer to a friend of mine who runs a clothing business.

This is the first real test of the pivot I wrote about a few weeks ago.

Good for him. Less good for me, because now I have to actually do it.

Here’s the thing I didn’t fully think through when I came up with this offer: getting the yes was the easy part. The hard part is showing up at his office and finding a workflow that’s actually worth automating. I don’t know his business. I haven’t seen his processes. I’m walking in with a method but no specific solution.

I have some guesses. Order intake from suppliers, customer service emails, inventory updates, something around their webshop. But these are guesses from someone who has never set foot in a clothing business. For all I know the real bottleneck is something I haven’t thought of at all.

That’s probably fine. The whole point of going in with the free-first offer is that I don’t have to be right on the first try. I can look around, ask questions, find something, and ship it. The free part buys me the room to be wrong.

What I’m actually nervous about is showing up and not finding anything worth automating. Or finding something but realizing it would take three months to build properly, not the quick win I had in mind. Or building the thing and watching it not get used.

For now I’m just going to help him out and see what comes from it. No talk of money, no talk of what’s next. One workflow, free, see what happens.

Anyway. He said yes. So I’m going.

Key insight

The free-first offer isn’t only about being generous. It’s about buying yourself permission to not know what you’re doing yet.