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 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 […]

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 […]

Last year I sold almost all of an Apple position I’d spent fifteen years building. The decision had nothing to do with the stock price. I assumed it would keep climbing for a while, the way Intel kept climbing long after it stopped being the company that defined its industry. Great companies run on a […]

Years before I co-founded BiTE, I worked remotely for a company that wasn’t a remote company. I’d moved from California to Tennessee, and they kept me on, but I was the only person they had working from outside the office. It mostly worked, because I’d been there long enough to know everyone. But there was […]

I’ve been overjoyed watching the Western Conference Finals this past week. I know. Some of you reading this don’t go in for “sportsball” talk, but if you bear with me (or skip ahead a few paragraphs) I promise I have a point. The Thunder and the Spurs are two extremely elite basketball teams. Not only […]