Writing

Recent Thinking

Written as I work through the shift. Increasingly how new clients and founders find me.

All essays
01 Everyone Is Learning to Grade AI. Who Owns the Answer Key? Evals are a skill. The standard behind them is a job, and it needs a name next to it. → 02 From Running Product at Yahoo! to Building My Own AI System One conversation, on the Meta @Scale podcast with Francois Richard. Video, 41 minutes. → 03 AI Is Splitting Your Teams and Merging Your Executives Two executives who no longer have to negotiate are one executive. → 04 AI Cannot Get Six People in a Room to Align Building compressed. Then analysis compressed. Then everyone showed up with their own prototype, and the room got harder. → 05 You Cannot Price a Standing Refusal Until You Remove It His most valuable output was work that did not happen. Now we are training models on a record that cannot see it. → 06 Your AI Rollout Is Missing a Kill Rate Faster building without faster deciding doesn't compound. It just hands you a bigger pile. → 07 From Individual AI to Team AI: The Next Problem Personal AI wins are real. Team AI wins are a different problem. → 08 AI Isn't a Tool. It's a Team You Have to Design. Six months ago I called this 'using AI.' I don't anymore. → 09 When AI Adoption Stalls Inside an Organization People blame the tools. Or the training. → 10 I Built an AI System. It Had to Earn Its Access. In my quest to continue to learn about all things AI, I started with OpenClaw. → 11 Betting on AI as THE Intelligence. Here's What That Misses. Two CEOs are betting AI is the work. The labs that sold them the AI just spent $11.5B betting against them. → 12 AI Made the Build Faster. It Didn't Make Users Faster. When I managed Yahoo Mail, 225+ million people used it every month. → 13 Most PMs Quit AI Too Soon. Reach the 4-Hour Mark. Marty Cagan ('PM guru') said two important things over the last 10 days. → 14 AI Doesn't Need More Builders. It Needs Thinkers. I gave a talk at Pie Fi (a builder community) in Santa Cruz a couple weeks ago. → 15 AI Didn't Unlock Everyone. It Unlocked the Connectors. My thinking on who AI actually unlocks has evolved. Here's what changed it. → 16 AI Won't Replace Your Kid. The Kid Next to Them Might. Every week someone asks me some version of the same question. → 17 AI Didn't Unlock Everyone. It Specifically Unlocked Product Managers. There's a specific profile of person AI unlocks. Not the programmer. Not the non-technical person. The one in between. → 18 Your AI Doesn't Know What Your Team Wouldn't Ship Every company runs on judgment nobody wrote down: what your team wouldn't ship, what good means here. Your moat, and your blind spot. →

Landed here from a note? The writing is the thinking. The rest of it is on the home page: what I've built, what I run it on, and how I work with a team. Or hand the whole picture to your AI and ask it anything you'd ask me.

What I've built →
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