Writing.
A weekly-ish letter on building things in the AI era. Each issue is also published on Substack. That's the canonical home, this is the archive.
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What Do You Do While You Measure?
AI compressed building from months to hours, but measuring whether anyone wants what you built still takes weeks. The Lean Startup loop is lopsided now, and nobody's found the new rhythm.
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Goals, Not Tasks: What Actually Makes an AI Agent
I ran 20 identical tests changing only one variable — task vs goal framing. The results reveal what actually makes AI behave like an agent, and it's not architecture.
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The Mythical Man-Machine Month
On super ICs, Brooks's law, and where one person and AI beats a team.
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I tried being an AI prepper for the weekend
I spent a weekend testing local AI models to see if I could work without cloud APIs. Here's what works, what doesn't, and what it costs to go off-grid.
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Agent-first is the new mobile-first
Why some agent-native tools are homeruns, why others barely work, and what it means if you're building one.
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Find Your Fun Thing
Forget productivity. The best way to start with AI is to point it at something you actually enjoy.
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Cron Jobs, Not Agents
I built an AI pipeline that pulls from 100 sources every morning, runs everything through Claude, and posts a curated brief to Slack. The whole thing costs $1.50 a month.
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The 80/20 Compromise
The market for simple desktop tools has always been built on an 80/20 compromise. That compromise is getting worse every month.
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Treasure Maps
The indie founder ecosystem is full of tools that promise to show you what to build next. Most of them are selling the path, not the destination.
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Product-Person Fit
Enterprise champions aren't cultivated through account management. They're found — by building a product that matches how they already think.
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Coaching Claude
What I'm learning by teaching AI to make videos.
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Taste and Distribution
Why good execution is no longer enough.
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The Decision Engine
Delegation, AI, and the blank page problem.
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After the Spike
Scaling without losing what made you special.
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How to Make Your Vision Survive Translation
What happens when your vision gets passed from person to person.
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Is Your Product a Homework Assignment?
You've forgotten what it's like to be new.
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Don't Experiment on Your Team
The difference between understanding a framework and owning it.
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Turn Objections Into Conditions
Stop debating whether ideas will work. Ask what would have to be true for them to succeed.
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Responsive Doesn't Mean Yes
How startups deliver enterprise contracts without becoming consultancies.
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Build a Spike, Not a Triangle
Why startups shouldn't worry about technical debt, feature parity, or balance.
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Which Roadmap Path Are You On?
How to know what roadmap flexibility you actually have.
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Product Discovery Without Access
Lessons from building for users you'll never meet.
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The Type 53 Pattern
Product discipline from a century-old Cadillac.
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Winning at the Edges
Great products win by handling the edge cases others ignore.
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Conferences are rapid-fire customer research labs
How to use conference conversations to quickly test language, customers, and product bets. And bring back real insight.
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How are you handling Promise Debt?
Big contracts come with big compromises. You can still avoid roadmap takeover if you plan it right.