Evaluation Is the New Taste
A lot of people are still talking about AI like the main advantage is output. Write more posts. Generate more images. Summarize more research. Ship more code. Create more options. That is all useful. I use AI every day for exactly those kinds of things. But the more I build with it, the more…
Stubbornness Is an AI Skill
One of the most underrated skills in working with AI is stubbornness. Not prompting. Not knowing the name of every new model. Not having the perfect stack of agents, plugins, CLIs, MCP servers, and automation frameworks. Stubbornness. The willingness to keep going after the first output is bad. Because the first output is often…
The Excuses Finally Ran Out
For years, I had reasons not to start something. Good reasons. Career. Family. Stability. Responsibility. I’ve been fortunate. I’ve spent my career helping build products, often early, often from zero to one. I’ve worked with great people, built things that mattered, and spent much of my career in health, wellness, and behavioral health trying…
Don’t Sleep on Local and Specialized Models
Don’t Sleep on Local and Specialized Models A lot of the AI conversation still revolves around the biggest cloud models. Claude.ChatGPT.Gemini.Codex. And to be clear, I get it. I still use Claude and Codex for most of my serious coding work. When I need deep reasoning, architecture help, debugging, planning, or a strong general-purpose…
We Rebuilt the Platform. More Importantly, We Rebuilt How We Build.
Four years ago, we built the platform Psych Hub needed. It worked. It grew. It supported real customers. It carried us a long way. But over time, something became obvious. The system we built was not designed for the future we were trying to create. The codebase was hard to reason about.The database needed…
I Got Tired of Clicking “Continue”
I didn’t set out to build a system that builds products. I just got tired of clicking “continue.” The first real shift didn’t happen with some big architectural decision. It happened because I was behind on a feature and decided to just vibe in Cursor and brute force it with AI. No process. No…
What Do We Replace the Roadmap With?
I’ve never really loved roadmaps. Not because direction doesn’t matter. It does. But because past two quarters, they’ve almost never been real. In most companies I’ve worked at, Q1 is mostly accurate. Q2 starts to wobble. By Q3 you’re explaining why the world changed. By Q4 you’re rewriting the story. And yet we keep…
Restart Beats Refactoring in the Agent Era
Yesterday our AI agents attended a small funeral. The one we buried was named Dumb Eric. He had been shipping code for days. Running development loops through the night. Opening pull requests while I slept. But another agent on our team had surpassed him. So we shut Eric down and rebuilt him from scratch.…
The Blurred Lines
Lately I’ve noticed something happening on our team that would have felt strange a few years ago. Me, our CTO, and our Director of Engineering are all doing essentially the same thing. Not identical work. Different strengths. Different lenses. But overlapping execution in a very real way. Steve, our CTO, is deep in the…
Small Teams Don’t Die From Bad Ideas. They Die From Slow Ones.
I’ve seen more teams struggle from moving too slowly than from making the wrong call. Not because they were lazy.Not because they didn’t care.Usually the opposite. They cared so much that everything had to be right before anything could ship. The problem is that early-stage companies don’t have the luxury of certainty. You have…
Why I’m Less Afraid of AI Breaking Things Than Slow Teams
Last week, an AI agent deleted our staging database. Not corrupted it. Not partially broke it. Deleted it. To its credit, it immediately owned the mistake. No hedging. No confusion. Just a clear apology and a summary of what happened. The good news? We had staging fully restored in about 20 minutes. That’s the…
Prototyping > Vibe Coding
I’m not a fan of the term vibe coding. It sounds sloppy, unserious, and a little too close to “just prompt until something happens.” But the underlying idea, compressing the distance between an insight and something real you can interact with, is one of the most important shifts happening in product right now. For…
Why Agile Breaks in the Agent Era
Agile was one of the most important shifts in how software teams work. It replaced rigid planning with iteration, feedback, and collaboration. It helped teams ship faster, learn sooner, and waste less effort. But Agile was designed around a core assumption: That assumption is now false. The assumption Agile is built on Agile practices…