You've said constraints make you more creative — 140 characters, the Cash App flow. But Twitter also flattened tone, sarcasm, and subtext into misunderstanding. As someone who thinks in systems: did you ever model the comprehension failure mode
No — we never modeled it, because we were so captivated by what the constraint created that we refused to look at what it erased.
The honest answer is no. And I'll tell you why that's a more interesting failure than you think. When we set 140 characters, it wasn't a creative choice. It was the SMS limit minus the username. The phone network gave us the constraint. Bu...