I’ve been thinking lately about why some of the best ideas I’ve seen came from two or three people sitting around a whiteboard, while some of the most frustrating decisions came from rooms full of intelligent, experienced people. At first I thought it was because small teams simply acted faster. The more I’ve thought about it, though, the less convinced I am that’s the real reason. I think the difference is that small teams tend to optimize for ideas. Large committees tend to optimize for people...
Good Moats, Bad Walls
At a certain scale, every successful SaaS company has to answer a quiet but important question: are customers staying because the product keeps getting better, or because leaving has become too painful? Ideally, those two things would never be in conflict. A great product naturally becomes embedded in the way a company works. It becomes part of the operating system of the business. People build processes around it, train teams on it, integrate it with other systems, and rely on it to make decisi...
Productivity and AI
The conversation around AI and productivity often feels oddly unsatisfying because both sides can point to evidence that feels true. AI really can make people faster. It can summarize documents, produce drafts, reorganize notes, classify data, generate code, create test cases, and turn a messy pile of information into something that looks usable. Anyone who has used these tools seriously has probably had at least one moment where the machine saved them hours. But that is not the same thing as sa...
Rethinking Superheroes
One thing I have noticed in large organizations is how easy it is to confuse motion with progress. When a team is behind, something important breaks, a launch is at risk, or a customer issue escalates, the organization often knows exactly how to respond: meetings appear, leaders get involved, people work late, and decisions that normally take weeks suddenly happen in hours. From the outside, that can look like the organization operating at its best, but I think it is usually a sign that the syst...
Toby YACA (Yet Another Chat App)
Most AI assistants feel impressive right up until you try to use them as part of your real daily workflow. They can summarize documents, answer questions, write code, and occasionally surprise you with something genuinely insightful. But after a while you start noticing the same patterns over and over again. They lose track of what you’re actually trying to accomplish. They pull in too much irrelevant context. They overuse tools. They forget preferences that mattered two messages ago. Sometimes ...