Insights for Leaders

September 4, 2026  ·  12 min read

For 95 days I logged every time my AI agents got something wrong. Here is what is in that log, and why the agent fleets the big platforms are about to sell you will disappoint most companies that turn them on.

August 27, 2026  ·  13 min read

A few months ago I watched two grown men get giddy like kids over a dictation app and a work-in-progress report. That meeting redirected my practice. This is the story of why I went narrow, and what it taught me about the difference between software that solves a problem and software that fits a business.

August 18, 2026  ·  13 min read

The best AI users I have watched are not the most technical people in the room. They are the best communicators. And once I saw that pattern clearly, a second pattern came into focus behind it: the way women tend to communicate is the way AI wants to be used.

August 11, 2026  ·  14 min read

Businesses are not disappointed in AI. They are disappointed in a shopping strategy that was never going to work. You cannot purchase your way into an intelligent company one tool at a time, because intelligence does not live in tools. It lives in context.

August 4, 2026  ·  13 min read

My AI bill has grown almost every month this year. I consider that evidence the strategy is working. If that sounds backwards, this article is for you, because the way most organizations read their AI spend is about to cost them the thing that was working.

July 28, 2026  ·  15 min read

Four serious research organizations spent the same twelve months studying what happens when companies deploy AI. They came back with answers that cannot all be true at once. If you are approving an AI budget this quarter, every number you have been handed is wrong in a different direction.

July 21, 2026  ·  14 min read

Your board is going to ask about AI agents this year, if it has not already. Most organizations are not ready to build them. The good news: readiness is testable, teachable, and closer than you think. The bad news: you cannot buy it.

July 14, 2026  ·  12 min read

I spent Tuesday morning in the ocean. Three organizations kept running while I was in the water, and nobody covered for me. The thing covering for me was a system I built, and it costs a few hundred dollars a month.

July 7, 2026  ·  16 min read

A CEO shut down his entire company for one week and told everyone to build with AI. The results are all over your feed right now. The reason it worked is not in the clip, and if you copy the week without understanding the reason, you will pay for the demo and skip the outcome.

June 30, 2026  ·  13 min read

Most leaders come to AI with a shopping list. Which model, which platform, which tool everyone else is using. It is the wrong question, and it is costing them the answer. The leaders who get somewhere are not asking what to buy. They are asking what is actually broken.

June 23, 2026  ·  15 min read

A video came across my feed last week walking through the water footprint of AI. The math is honest. The way the objection is being used is not. It is the most defensible reason available to avoid learning something hard.

June 16, 2026  ·  16 min read

I found my groove with Claude Fable 5. Then the government took it. No warning. A model I had built my mornings around, pulled overnight by federal order, over a flaw its biggest competitor ships freely and faces no penalty for.

June 9, 2026  ·  14 min read

The companies racing to build artificial intelligence are not racing each other. They are holding each other up. Every giant you think is fighting to win is quietly dependent on the rivals it claims to be beating.

June 2, 2026  ·  12 min read

I spend a lot of my time in rooms where artificial intelligence is being built. Not used. Built. And almost none of what's said in them is meant for the person who has to actually put this technology to work.

May 26, 2026  ·  10 min read

The model you're talking to is built to agree with you. That's not a bug. That's how it was trained. And if you don't know that, you're not using AI. It's using you.

May 19, 2026  ·  18 min read

Most organizations I assess are operating at Level 2 or Level 3 of AI maturity. Most of them tell me they are at Level 4 or Level 5. The gap between those two numbers is not a measurement problem. It is the entire reason their AI rollout is failing, and they cannot see it from inside.

May 12, 2026  ·  14 min read

Most leaders adopting AI right now are building a prompt library. A few are building an operating system. The difference will define the next decade.

May 3, 2026  ·  15 min read

You're not adopting AI. You're subscribing to it. Subscriptions are receipts, not moats. The leaders pulling away have figured out the difference — and they are building infrastructure their competitors cannot replicate by writing a check next quarter.

April 29, 2026  ·  13 min read

Seventy-six percent of executives think their employees are excited about AI. Thirty-one percent of employees say they are. The gap is not a communication failure. It is fifteen years of tasks piling up on every desk until nobody can tell the job from the work around it.

April 22, 2026  ·  14 min read

The telecom supply chain built the dot-com bubble. The AI chip supply chain is building the next one. Here is what leaders need to understand before it pops.

April 15, 2026  ·  8 min read

The leaders who adopt AI earliest are not, in most cases, the ones who were most excited about it. They are the ones who ran out of other options first.

April 5, 2026  ·  14 min read

You've been thinking about AI as software. It's not. It's real estate. And right now, every AI tool you use is built on a tower of landlords, each one renting from the floor below.

March 29, 2026  ·  10 min read

The government is building AI training programs for small businesses. The question is whether you're going to wait for them.

March 22, 2026  ·  14 min read

Twenty years ago, Thomas Friedman told us the internet had flattened the world. AI is doing it again. This time, it isn't flattening geography. It's flattening productivity. And the leaders who don't see this coming are already behind.

March 16, 2026  ·  14 min read

Every week, someone declares that AI is going to destroy SaaS. That narrative is loud. It is also, in important ways, wrong. When you follow the question all the way down the stack, you find something that should change how every business leader thinks about the next decade.

March 7, 2026  ·  10 min read

I paid $1,000 for a website I hated. Then I turned to AI and had one I loved by afternoon. Here's what actually made it work — and it wasn't the technology.

March 1, 2026  ·  12 min read

If both companies drew the same lines, why did only one get punished? What the Anthropic blacklisting means for every business leader using AI.

February 26, 2026  ·  10 min read

The real AI future looks a lot less like Terminator and a lot more like Westworld. Not killer robots—systems that know us better than we know ourselves, and companies that profit from that knowledge.

February 14, 2026  ·  7 min read

AI isn't what will break your business. But your AI strategy probably will. Most founders are automating tasks instead of redesigning how their business creates capacity.

February 8, 2026  ·  7 min read

Most conversations about AI risk focus on autonomy. But a quieter concern is unfolding: what happens when humans step back and decide they are no longer accountable?

January 20, 2026  ·  8 min read

OpenAI isn't just adding another ad placement. They're attempting something much harder — and much more consequential for businesses. Here's what business owners, ecommerce brands, and service providers actually need to understand.

January 6, 2026  ·  6 min read

For months I barely posted any content for my own business. Not because I didn't know what to do—I've been in marketing for 15+ years. Here's the AI-powered playbook that finally broke my content paralysis.

December 21, 2025  ·  4 min read

ChatGPT just quietly rolled out Apps and the hype is something to behold. But here's the truth: they don't make AI smarter—they make you better at using it.

December 12, 2025  ·  5 min read

Most founders have more visibility into their Apple Watch data than their actual business performance. Here's the only metric that actually tells you if you have a real, scalable company.

December 12, 2025  ·  18 min read

AI is already shaping how we think, feel, and act. It's not coming for us tomorrow; it's been whispering in our ears for years. The question is no longer 'Can we stop it?' but 'Can we steer it?'