Welcome back. Issue three.

Quick news before we start: I’ll be speaking at Colorado Startup Week in September, on adding AI to the systems you already run without ripping any of them out. If you’re going, come find me.

Now the thing I can’t stop thinking about.

THE PATTERN

The pattern we keep seeing

Two numbers from a recent survey of small and midsize business owners. They only matter side by side.

66% now use AI. Up from 55% a year ago.

70% say they need more training to use it well.

Adoption isn’t the hard part anymore. Mastery is. Businesses got the tools faster than they got the judgment about where to point them.

Two companies can buy the same software in the same month. One aims it at the task eating fifty hours. The other aims it at something that was already fine. Same spend, completely different year.

FROM THE FIELD

The assistant that went looking

Devon Tilly runs three businesses. A window and door company, the construction industry’s leading podcast, and a Colorado retreat property. Three websites, zero developers on staff.

The website work just sat there for a long time. Not broken, not updated. The thing every busy owner keeps meaning to get to.

Here’s what surprised me: the hard part was never writing the updates. It was memory.

Most AI forgets everything the second the session ends. You re-explain your business every time you sit down, which means the tool is useful in bursts and useless for anything ongoing. Our first version had exactly that problem.

So we rebuilt it around memory. Context that survives between sessions. Connected to all three sites. Picks up where it left off.

Then this happened. Someone on his team flagged a typo in a blog post. The assistant fixed it, then went and checked the rest of the site, found the same misspelling in five other places, and asked if it should fix those too.

Nobody asked it to look.

Devon’s words: “My first employee, my assistant, reborn. And now she’s adding value in a way I never would have dreamed of.”

That’s the difference between having AI and using it well. Not a better model. A system that remembers the business it works for.

TRY THIS TOMORROW

Read your own software bill. Not to cancel anything, to ask better questions.

Every line over $500 a month gets three:

What job does this actually do? Not the feature list, the job.

How much of that job is checklist work, same steps in the same order every time?

When did we last question this line?

You’re hunting for one thing: a tool whose whole purpose is moving information around and checking it against rules. We reviewed a stack recently with a tool billing for 40 seats and nine actual users, doing exactly that. Nobody had questioned it in three years. It renewed automatically, and switching always looked harder than the line item, right up until someone did the math out loud.

Twenty minutes. No vendor required.

SIGNAL CHECK

What we’re seeing

1. Buyers are asking sharper questions. Six months ago it was “what can AI do.” Now it’s “what does this cost to run after the build.” That shift from capability to economics is what a maturing market sounds like.

2. Owners are separating build cost from run cost for the first time. The build happens once. The compute is forever. Teams that understand the difference budget better and get burned less.

3. And the trend nobody’s writing about: businesses that piloted something this year go into planning season with receipts. Everyone else goes in with slides. That gap compounds all next year.

WORTH KNOWING

The adoption that produces nothing

There’s a version of AI adoption that looks like progress and produces nothing.

Everyone gets licenses. There’s a training session. A few people use it for email. Six months later the renewal comes up and nobody can name one thing that changed.

What separates that from the real thing isn’t the tool or the budget. It’s whether one specific, painful, repeated task got picked and killed.

Pick the task first. Nothing works without it.

If you want help finding yours, that’s a 30 minute conversation:

One small ask

If this was useful, forward it to one business owner who’d like it. That’s how the Brief grows.

Until next time,

Shawn Kercher

Co-Founder & CTO, HummingAgent AI

P.S. Want to share this issue? It’s also on LinkedIn