This sounds weird, but it is actually probably a good policy. Even if you don’t believe AI is conscious (I don’t), it stands to reason that you don’t want future models trained on endless content of humans being rude to models. The models only understand the data they’ve been trained on, or what they run into in their interactions, so if you want safe and aligned models we probably want AI to have lots of good interactions in their training data. Anthropic may have more extreme beliefs than this (though even if they didn’t, you may want to word policies like this), but this is sort of an easy Pascal’s wager for AI. Just be nice to the AI.

Yep. Except: 1. This was about important internal tools. The team was stuck in some architecture nightmare of their own doing (writing it in rails but headless, with graphql api, and a SPA react app, constantly needing frontend engineers for changes). I call this kind of thing 'cosplaying an enterprise production app'. All that complexity was in the way and using straight rails was perfect in that case. 2. I make calls like this all the time. Usually someone on the team asks me to. They see what needs to happen but don’t want to be the bad guy. I’m happy to just make the call if I agree with the premise. Saves enormous amounts of meetings and change management etc. Sometimes this is jokingly referred to as Founder-mode-as-a-service here. 3. For ten years I’ve also run an internal podcast called Context, where I revisit decisions like these and explain the reasoning so everyone can learn from them. This is helpful to give people all the variables that were considered and why this was the choice made given the information available at the time. I want to teach how to make such decisions effectively without needing me. Sunk cost fallacy is a problem. 4. Any notions that Shopify is succcessful despite of me doing this, instead of because of it, will have a hard time making their argument come together I think 😄 the part of 'two weeks later tobi learns about...' is nonsese and the pivot of that project up there happens one of the more successful examples of interventions. But getting the company to work effectively with great architecture and low technical debt baggage into the right direction is literally the job, so guilty as charged I suppose. But there are always cope stories floating around like this because they are more fun, than saying 'somehow we needed tobi to stop doing silly architecture astronautics'. I can totally see that.

Sidney Crosby letting this Canes fan hear it after going on the power play 😆

United CEO on @Flighty. 🙏 Impressive clarity and customer focus throughout the interview. stratechery.com/2026/an-inte…

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