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Daily one-pagers about AI, leadership, technology, and being human.

johnmaconline

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August 20, 2026 2 minute read

Does AI Know Who You Are?

AITechnologyThe250

50 years ago, it was “Do you have a listing in the yellow pages?”

The basic listing with your name, address, and phone number was free. Your clients could pick up the book and search for you. To make sure they’d find you, you could pay to upgrade your listing with enhancements, placement, and advertising.

The internet put the Yellow Pages out of business. Rather, Google put the Yellow Pages out of business. Because then it became, “Do you have a web page?” Your clients could Google search for you. To make sure they’d find you, you could pay Google to upgrade your listing with enhancements, placement, and advertising.

I think the question is about to change again. I think it’s gonna be, “Does AI know who you are?”

Your clients are asking AI:

“Who can help me with this?”
“What product should I use?”
“Who knows how to solve this problem?”

And AI will give them an answer.

So what’s the new Yellow Pages listing? What’s the new web page? And what do you need to do to make sure AI knows you exist?

When you ask AI itself this, it provides the following:

That means the future version of “being listed” may not be about owning a webpage. It may be about making your business legible to AI: clearly stating what you do, who you help, where you operate, what problems you solve, what your products are, and why someone should trust you.

I don’t yet know how we do that, but I think we’re about to find out.

August 19, 2026 1 minute read

Accounting for AI Waste

AITechnologyThe250

If you build a deck, a set of steps, or some other structure out of wood or pavers, you’ve got to account for the waste.

When pricing and ordering your materials, you add about 10-15% to account for waste. That waste comes from angle cuts, standard board and paver sizes that don’t match up to your dimensions, and also mistakes.

At the end of the project, you’ll be left with a pile you gotta get rid of.

I’m finding the same is true when using AI to build.

I’m always left with a pile of code, documents, other files lying around, and especially the wasted tokens spent.

I suspect there’s a point in the future where we start accounting for this waste. This might be an opportunity.

Figure out how to help others account for and then minimize their AI waste.

August 18, 2026 1 minute read

Scaffolding of Creativity

AIHumanTechnology

The Wright Brothers created an amazing invention.

But it was ugly. Two ungainly wings. Wood and canvas. Brown and tan. Struts and cables. Plus, it was terribly uncomfortable to ride in.

Contrast their plane with a modern F-22. A work of art in addition to a modern scientific achievement.

And you might correctly say, “Yeah, but the science around everything in airplanes has come so far since the Wright Brothers.” And you’d be right. The F-22 is the culmination of thousands of scientific and engineering achievements since 1903.

But I’m wondering, “Could someone have drawn a sketch of an F-22 in 1902 before the Wright Flyer made it’s appearance? Could they have even conceived of it?”

I think the answer is no.

Nobody, no matter how creative, could have drawn a picture of an F-22 and said, “Someday we’re going to fly through the air in one of these things.”

Creativity, along with science and engineering, stacks on the scaffolding of what comes before. One idea begats the next. And so on.

We don’t yet know where we’ll take AI or where AI will take us.

But its gonna be a fun ride.

August 17, 2026 1 minute read

A Movie Life

HumanLeadershipThe250

An interesting question to ask yourself:

Could someone make an interesting biopic about you?

Which then begs the next question:

If not, are you OK with that?

Which then begs:

If not, what are you going to do about it?

Nobody has to live a movie life. Movie lives come with lots of scars, failure, and turmoil. That might not be what you’re looking for, and there’s nothing wrong with that.

But if you want to live a movie life, today’s the day to get started.

August 16, 2026 2 minute read

AI and the Compounding of Ideas

AIHumanThe250

There are two basic methods for generating compounding ideas.

One is personal. You start with one small idea.

“I want to make my own little app for tracking my To Do list.”

Start by creating the simplest version that serves the purpose, and play around with it. Fix this. Change that a little. Blue not green. Oh, add this. What if…

And if you keep going, repeating the build and use cycle, more and more ideas keep coming.

The ideas compound. But only if you start, build, test, and keep iterating.

AI enables this because it can be the builder. It takes away the difficulty of turning your idea into something concrete. And it can also accelerate it because of how easily it can generate iterations.

The other method requires humans.

This is the method that we’ve been using for thousands of years.

You have an idea, and you bring it to another, or several others. Each person brings their own perspective to the table, and that sparks their own ideas. So you discuss, argue, and iterate.

The ideas compound because of the varied perspectives built upon personal histories and values.

AI doesn’t really help us here. Sure, you can simulate the “discuss, argue, and iterate” loop by using the LLM as your team, but AI doesn’t have a perspective built on personal history. It has no viewpoint.

AI gives us a great new way to compound ideas through rapid iteration, but it can’t replace the human perspectives that have always made collaboration so valuable.

August 15, 2026 1 minute read

0% 50% 200%

AIHumanLeadership

Great article from Dan Shapiro.

OK, I admit I like it because it agrees with me (less with more plus.

0% — Status quo. Ignore. Don’t invest.

50% — More with less. Same targets. Enable your people. Cut some people. Cut costs.

200% — More with more. Double your targets. Launch your people. Expand your product line. Improve your quality. Get it done faster. Blow up the competition.

You might have some success with 50%, but at least one of your competitors has 200% in their sights. Who’s gonna win that battle?

More with more.

For all the fearmongering around AI, it’s the more-with-more crowd that will win.

Lean into 200%.

August 14, 2026 1 minute read

An Optimistic AI Future from Zuck

AIHumanLeadership

Throw a rock and you’ll hit a doomsday AI prediction.

Dario from Anthropic leads the fearmongering by basically telling everyone who’s just coming out of school or who works in a white-collar industry, “Hey, Claude’s gonna take your job. Sorry.”

Sam from OpenAI is less overt, and way more savvy (cagey?), but I think inside the OpenAI fortress of $100M engineers, he agrees.

You know me. I’m not a fearmonger. Also, I’m not closing my eyes to the reality that AI is and will continue to change how the workforce looks. AI has totally transformed how I do my work and how those on my team do their work.

But I’m an AI optimist.

And now so is Zuck.

Here’s the TL;DR:

Our AI future can be one where superintelligence is widely distributed and turns billions of people into more capable inventors, learners, and entrepreneurs. AI can make individuals dramatically more capable, rather than simply replace them.

To help usher that in, Meta will be open-sourcing their models and tools. More eyes. More ideas. More people. Less friction.

Kudos to Zuck.

I’m on board. I can’t wait for the future.

August 13, 2026 1 minute read

It’s Not You

HumanLeadershipThe250

If you hear that, assume it’s you.

Not because the person who said it is lying. They might be, but also, they might be completely sincere.

However, if you just assume it is you, then you can purposefully and definitively move on.

Go where you’re valued.

August 12, 2026 2 minute read

Self-Awareness

AIHumanLeadership

Who are you in the world of AI?

If AI can do what you do, you have two choices:

  1. Do it better.
  2. Do something else.

Right now we’re in a phase where people still want to do one because that’s what they know or have always done. And also, think they can indeed do it better.

It’s possible. Studies still show that AI can’t do it better than the very best humans (but not necessarily faster or cheaper) for now. This won’t last long, however. If you want it this way, you must lean into the art of what you do. Find the art. Master the art. Better is in the art.

Two is probably a better path for most of us.

Pick a trade or human-facing work, or there is plenty of work in genres that can’t or won’t lean into AI yet due to security or other concerns.

Another way is to recognize that AI will need a boss. It will always need a boss at some level. AI rewards people with ideas and the gumption to try stuff.

Figure out how to get AI working for you or you’ll be working for AI.

August 11, 2026 1 minute read

UFOs

HumanThe250

The government just released more UFO files.

UFOs are fun, and I’ve been thinking about them since I was a kid.

If you don’t want to dive into all of the info, here’s a summary:

Yes, people really are seeing things.
No, we cannot identify all of them.
And no, we still do not have publicly verified alien spacecraft.

That’s all. This is just a UFO appreciation post.

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