Steph Ango aka Kepano (Website, X) is a designer, writer, entrepreneur,and toolmaker, best known as the CEO of Obsidian, a powerful and flexible writing and thinking tool. Steph's education is in biology and industrial design, but he is true multi-hyphenate creative, working across mediums including software, hardware, supply chain and packaging, words, wood, furniture, ink, color schemes, open-source systems, video, podcasts, and more. Above all, he makes tools—deeply opinionated ones—designed to reduce friction for himself and others in the act of creating. Steph joined Obsidian after initially contributing as a fan and enthusiast and impressing its co-founders, Shida Li and Erica Xu. Under his leadership, Obsidian has grown into one of the most beloved and powerful independent software tools in the world, with millions of users. As a daily user myself, I rely on Obsidian for my research and thinking for this podcast. Before Obsidian, Steph founded Lumi and Inkodye, the former of which was acquired by Narvar. Beyond design, Steph is one of my favorite writers. His concise, sub-500-word essays have shaped my thinking on design, software, learning, agency, constraints, and creativity. While we couldn’t cover all of his ideas in this conversation, we explored many of them in what became my longest conversation to date—one that is packed with wisdom. I believe these ideas will challenge you in unexpected ways and push you to be more creative, agentic, and optimistic. Transcript for episode 8. Timestamps: (1:56): Constraints and style (11:51): Aggressively planting creative seeds but being patient for them to grow (17:42): Stadium of past and future selves (22:34): Asking what can be removed and making incremental progress (28:47): Building a product and company (Obsidian) with the "constraint" of ideology and principles (38:52): Using Obsidian makes Steph better at building Obsidian (44:09): What makes for good design and seeing the world as something designed (by nature or man) (53:11): What makes a good tool? (56:20): Thinking tools and Obsidian (1:04:32): "In good hands" and caring more than anyone else (1:21:38): Engaging all five senses (1:24:46): Creating cohesion or your own cinematic universe (1:30:43): How to time travel (1:33:08): Designing for digital durability or permanence & "File over app" (1:56:46): Investment and "selfishness" in extending your light (2:05:54): Choosing problems to work on (2:09:10): "Nibble and your appetite will grow" (2:12:31): Compounding (2:19:55): "Caloric energy is precious" (2:26:21): "Earth is becoming sentient" (2:39:31): Busy being born and sharing along the way (2:42:11): Love and freedom Links Style is consistent constraint Buy wisely Stadium of selves What can we remove? File over app Obsidian Manifesto In good hands Pain is information Quality software deserves your hard‑earned cash Don't delegate understanding Nibble and your appetite will grow A little bit every day Caloric energy is precious Erewhon by Samuel Butler Earth is becoming sentient Agents of chaos Concise explanations accelerate progress Always learning, always teaching Six definitions of love Dialectic with Jackson Dahl is available on all podcast platforms.Join the ⁠telegram channel for Dialectic⁠Follow ⁠Dialectic on Twitter⁠Follow Dialectic on InstagramSubscribe to Dialectic on YouTube