Culture of Pilgrims: What Great Teams Look Like

All links and transcript at dialectic.fm/ryo-lu

Ryo Lu (Website, X) is the head of Design at Cursor. Prior, he was a designer at Notion, Stripe, and Asana, working on some of the most influential software tools of the last decade. He is now focused on building the next generation of tools for making software.

Our conversation is an extensive exploration of Ryo's design philosophy, which is anchored in his recurring mantra: "it's all the same thing." He sees the world as fundamentally modular, where simple rules and patterns endlessly recombine to create emergent complexity. For Ryo, design is consciously participating in this process: seeing through the surface to understand the underlying structure and rearranging it into new forms. This means constantly moving between simplicity and complexity, chaos and order, bare material and highest levels of abstraction.

We discuss how his process has evolved with AI. In the past, designing in tools like Figma felt like painting; now, working in Cursor feels like sculpting clay or finding David in the marble. So much of his philosophy is about getting closer to the material—in this case, code—and letting it provide feedback. There is no better example of this than his personal project, ryOS, a nearly full-on operating system he built entirely in Cursor. It is soulful, deeply personalized, and the opposite of "AI slop."

This is a philosophical discussion about designing things that feel "true" or even "inevitable," but it is also a practical one. We talk about balancing agility and quality, allowing for "slack" in systems, and how to create soulful things with AI. Ryo is a profound thinker, but he is also a prolific doer, and it is this marriage that makes him so effective. I hope you are inspired to get closer to your own material, to be more flexible and dynamic, and to expand the boundaries of what you can personally create.

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Dialectic is now presented by Notion. I am now focused on Dialectic full-time, thanks to their support. You can read more about why Notion embodies Dialectic's values and our partnership announcement here.

Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts.

Timestamps

• 0:00: Notion Announcement & Dialectic's Future
• 4:45: Intro
• 7:46: "It's all the same thing!"
• 17:25: Technical and Conceptual Readiness and How AI Helps us Deal with Complexity
• 20:58: Designing for true-ness and inevitability
• 27:28: Practicality and False-Compromise
• 33:45: Working with Material and Different Ways of Thinking
• 44:06: ryOS and Designing for the Full Spectrum of Users
• 59:39: Allowing for Slack and Some Amount of Chaos in Design
• 1:04:55: What is Cursor, Conceptually?
• 1:10:33: How Using Cursor Evolves
• 1:15:50: Designing for Power While Not Alienating Users
• 1:19:59: How Ryo Designs at Cursor: Abstractions, Writing, Prototyping
• 1:23:57: Process, Creating Soulful Things with AI, Refining Taste
• 1:31:08: Balancing Agility and Quality, Chaos and Order
• 1:37:00: Great Teams and Great Products
• 1:39:41: Grab Bag: Human Tech, Why Tools Need Stories, Why Cursor Isn’t a Slot Machine, Notion & Cursor, Steve Jobs, Liquid Glass
• 1:56:16: Tenderness & Empathy