“When you make something with material, it always says something back to you that you didn’t expect.” That’s the heart of my conversation with Matt Webb — writer, technologist, and creator of Poem/1, the clock that tells the time in AI-composed verse. We talk about ”design pathfinding”, why inventing in the AI era means making things before you fully understand things, and how jokes, demos, and small experiments can reveal unexpectedly serious possibilities. Matt walks through the origins of his app Galactic Compass and his clock Poem/1, along with his approach to note-taking, writing, Kickstarter, and building a creative practice around curiosity. Matt is exceptional at staying sensitive to the feelings objects evoke and following strange ideas wherever they lead. Even into blind alleys, or to communist dolphins.