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.
-
The Mythical Man-Machine Month
On super ICs, Brooks's law, and where one person and AI beats a team.
-
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.
-
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.
-
Find Your Fun Thing
Forget productivity. The best way to start with AI is to point it at something you actually enjoy.
-
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.
-
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.
-
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.
-
Product-Person Fit
Enterprise champions aren't cultivated through account management. They're found — by building a product that matches how they already think.
-
Coaching Claude
What I'm learning by teaching AI to make videos.
-
Taste and Distribution
Why good execution is no longer enough.
-
The Decision Engine
Delegation, AI, and the blank page problem.
-
After the Spike
Scaling without losing what made you special.
-
How to Make Your Vision Survive Translation
What happens when your vision gets passed from person to person.
-
Is Your Product a Homework Assignment?
You've forgotten what it's like to be new.
-
Don't Experiment on Your Team
The difference between understanding a framework and owning it.
-
Turn Objections Into Conditions
Stop debating whether ideas will work. Ask what would have to be true for them to succeed.
-
Responsive Doesn't Mean Yes
How startups deliver enterprise contracts without becoming consultancies.
-
Build a Spike, Not a Triangle
Why startups shouldn't worry about technical debt, feature parity, or balance.
-
Which Roadmap Path Are You On?
How to know what roadmap flexibility you actually have.
-
Product Discovery Without Access
Lessons from building for users you'll never meet.
-
The Type 53 Pattern
Product discipline from a century-old Cadillac.
-
Winning at the Edges
Great products win by handling the edge cases others ignore.
-
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.
-
How are you handling Promise Debt?
Big contracts come with big compromises. You can still avoid roadmap takeover if you plan it right.