Here is how the post you’re reading right now got made. I keep an index of my past writing and a backlog of ideas: things I find myself saying in conversations that never quite made it onto a page. Each week I brainstorm with Claude about which idea is timely/relevant/interesting. Then I have Claude ask […]

Over 30 years ago, a CS professor of mine dropped a piece of wisdom as an aside in class. Dr. Soroka told us that every time he fixed something in a program, he got a little jolt of happiness. A little high. And he’d noticed something curious: the size of the high was not proportional […]

Boris Cherny, the head of Claude Code at Anthropic, said something last week that should sound familiar to anyone who’s read this blog: “The verification is probably the single most important thing that people do not get right.” The skill in working with AI, he argued, is less about prompt engineering and more about handing […]

Years ago, listening to Horace Dediu’s podcast, I heard Bob Moesta interviewing Horace about a car he’d recently bought. Bob was walking through the purchase the way he does, when Horace mentioned something about gas mileage. Bob paused the interview. “Did you see what just happened? Horace just tried to tell me he got a […]

Years ago we built a dating app called Zazazu. At its heart was an in-app economy more complicated than anything a dating app had tried before. The original model was simple: a straightforward 1-1 currency per transaction. Then the business evolved, the way businesses do, and the founders needed something entirely different: free-to-play, a multi-tiered […]

There are only two modes a company can run in: Expansion or Extraction. And it isn’t just companies. A team, an economy, a whole country is always doing one or the other, even if the underlying choice isn’t surfaced or clear. Expansion means you still believe there’s more to reach for: more customers to win, […]

Somewhere along the way, “minimum viable product” stopped being a meaningful concept and drifted into product lore. It’s a term everyone knows and yet almost no one can define the same way. Saeed Khan went so far as to argue the term (and other Product terms) has lost so much shared meaning it’s worth retiring. […]

Sixteen years ago, in the early days of the App Store, we built an app called The Red Carpet. It let you follow the Oscar nominees, wrapped around an audacious hook: guess every winner correctly and win a million dollars. The contest was real. We’d secured a $1M policy from Lloyd’s of London, gotten bonded […]