There’s an article going around by Alex Lieberman called 30 Features of an AI Native Company. Matt and I have been somewhat obsessed with it internally, enough that we’re going to work through it on the show over the next few weeks. It’s a good list. It asks what the perfect design of an organization […]
I Burned Two Billion Tokens for $125. That Number Is a Business Risk.
It rained all weekend, so I built things. Three projects. About 20 hours across two days. Up to 10 simultaneous agents running in Codex, kicked off as separate work trees so they wouldn’t collide with each other. When I looked at the usage numbers afterward, I had burned two billion tokens. My bill was roughly […]
Your Team Automated the Wrong Thing And LinkedIn Just Built a Button to Prove It
What the Numbers Are Actually Telling You LinkedIn now has a complaint button for AI-generated content. Users see a post, decide it’s slop, click the button, and a negative signal goes straight back to the algorithm. One click. No friction. That button didn’t appear out of nowhere. It appeared because the platform had no choice. […]
Your Organization Picked the Most Powerful AI Tool. Here’s Why Nobody Is Using It.
The Question Most Leaders Skip When Choosing AI Tools There’s a conversation I keep having with leadership teams, and it goes roughly like this. They evaluated tools. They did the research. They looked at capability benchmarks, sat through vendor demos, maybe ran a pilot with their most technical people. They picked the one that scored […]
You Didn’t Buy an AI Problem. You Inherited a Factory Problem.
The Factories That Got Electrification Wrong When electric motors became commercially available in the early 1900s, factory owners faced a decision that probably felt obvious at the time. They had a steam turbine. Now there was a better power source. So they swapped one for the other, kept the building exactly as it was, and […]
Your Team Is Using AI All Day. So Why Isn’t the Business Growing?
The Uncomfortable Gap Between AI Efficiency and Actual Growth Here’s something I keep running into with the business owners and senior leaders I work with: their teams are using AI. Genuinely using it not just dabbling. They’re clearing backlogs, tightening operations, replacing tools, building internal workflows that would have taken months before. By every visible […]
Your Vibe Coder Is Building. Does Anyone Know What They’re Building?
The Citizen Developer Wave Has a Governance Problem Every organization with 50 or more people probably has someone doing it right now. Maybe it’s the ops manager who discovered Claude and started automating her own workflows. Maybe it’s the analyst who connected your CRM to an LLM through an API and saved himself three hours […]
The Forward Deployed Engineer Land Grab Is Real, And Mid-Market Companies Are Being Left Out of It
Anthropologic and OpenAI didn’t suddenly get interested in consulting. What they built forward deployed engineering organizations backed by billions from Blackstone, Goldman Sachs, TPG, and Advent, with service partnerships running through Bain and McKinsey, is not a consulting play. It’s a token economics play. And understanding the difference is the most important thing a mid-market […]
You Already Have the People. You Just Haven’t Given Them the Structure.
The most common thing I hear from mid-market leaders about AI goes something like this: “We want to move on this, but we don’t have the technical staff to pull it off.” It sounds reasonable. It’s also, in most cases, the wrong diagnosis. Wyatt Barnett is Head of AI at the NCTA the Internet and […]
Anthropic Picked the Wrong Name. Here’s What Claude Code Actually Does.
When Anthropic named their agentic tool Claude Code, they made a decision that cost every non-developer one of the most powerful productivity applications available right now. The name did exactly what bad names do: it told a large portion of the people who would benefit most from the tool that it wasn’t built for them. […]










