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Business & AI.

Building companies, exploring AI, and staying open to what comes next.

9 stories in Business & AI

Idea Overflow

The latest

The Optimism Queue

What happens when the tools finally catch up with your imagination? During the dot-com years, there was a particular kind of failure I remember almost as clearly as the excitement of what we were building. We were creating applications…

20268 stories

Context Is King

The internet needed content. AI needs to understand why yours matters. I was fortunate enough to participate in the dot-com era, back when every company suddenly needed a website and very few of us knew exactly why. We were building things as quickly as we could, occasionally with a business

The Company Soul(.md)

Why the first AI agent you build shouldn’t be an assistant. I’ve spent most of my life building organizations of one kind or another. Some were startups. Some were manufacturing companies. Today I split my time between running a property management company and building an AI software

The Hidden Layer of AI That Finally Started to Make Sense to Me

I have been trying to understand why AI sometimes feels like magic and other times feels like a really confident intern who completely missed the point. That sounds sarcastic, but I mean it honestly. Some days I use these tools and feel like I am looking at the future. Other days I spend twenty minutes

The Second Brain You Didn’t Know You Had

Over the last few weeks I exported roughly 3,600 conversations from the AI tools I’ve been using. Ideas. Questions. Half-finished thoughts. Business strategies. Experiments. Dead ends. A few good insights buried in a lot of noise. I pushed all of it into Obsidian and visualized the connections. What came back surprised me. Not because it

The Next Management Revolution: Businesses That Run Experiments While You Sleep

Recently I came across a small open-source project from Andrej Karpathy, one of the researchers behind Tesla’s AI systems and earlier work at OpenAI. The project is called autoresearch. It’s a simple idea, almost deceptively so, but the implications are larger than they first appear. The system runs experiments automatically. It proposes a change, runs

Highest and best use?

I wrote recently about businesses gaining staff they never have to hire. Some people heard: fewer jobs. I hear something different. For a long time we’ve had a quiet inefficiency inside organizations — not a shortage of people, but a misplacement of people. Look at a normal day in almost any company. Formatting documents.Rewriting emails.Copying

Pondering AI – more than a tool?

Over the past few months I’ve been spending late nights experimenting with something most small and mid-sized businesses don’t yet realize is about to change their operating model: they’re about to get staff they never have to hire. Not chatbots. Operators. I’ve been working with OpenClaw — an open-source LLM agent framework — and the

20251 story

Retire or jump on the AI train?

I recently had a friend ask why, with retirement looming, I wasn’t simply playing more pickleball. It’s a fair question—I certainly enjoy playing—but truthfully, I’ve never been more excited professionally than I am right now. Why? Because AI agents are set to become this year’s defining technological trend, reshaping industries and offering unprecedented opportunities….