Better to be the chooser

I have a guilty pleasure, and it’s a newsletter I haven’t really tried to sell you on.

It’s called Toll Stack, and here’s the part I don’t usually say out loud: I build every issue with AI, on purpose, start to finish. I took a stack of knowledge — books, frameworks, my own experience — and turned it into a KPack. Then I asked that kpack, working off the same corpus, to help me write both a book and a newsletter out of it. The articles read well. To me, anyway. Some people would call that AI slop, and I’m not going to pretend they’re wrong to wonder. But even if it reads a little too smooth in places, the lessons underneath it are real. I’d rather ship something useful that sounds a bit off than sit on something true and never say it.

That’s actually the best part, if I’m honest. An idea hits me — something like that bartender, from this week’s issue — and I go sit with the kpack and the corpus and turn it into an article. It’s a genuinely fun way to work.

I’ve got issues written through sometime in 2028. That’s not a brag, it’s just what happens when the loop is fast and you don’t stop feeding it.

Here’s the part I haven’t said publicly. The job market has been brutal for someone my age with my background, and I’ve started to think Toll Stack, and the corpus behind it, might end up being one of my real paths to making money — maybe the main one. Better to be the chooser than to sit around waiting to be chosen. And the whole thesis of that corpus is built for exactly this moment. Most creators and businesses have built the audience, the product, the offer — the hard, visible part. What they haven’t built is the revenue architecture underneath it: the email capture, the flows, the upsells, the toll booth that turns attention into repeat revenue instead of a one-time click. That’s the part someone with my skills can walk in and build for them. Not a pitch deck. A toll booth.

The bartender in that cartoon isn’t running ads. He’s just useful enough, consistently enough, that people mention him without being asked to. That’s the whole model. I’ve been running Toll Stack the same way — not pushing it, just doing the work and letting it sit there. This is me pushing it, a little, for once.

If things ever go sideways for me, you’ll probably find me living out exactly what that newsletter teaches. Quietly. The way it tells you to.