Dreaming of software that makes us more human, with Linus Lee

Linustalks how tech can amplify or diminish our agency, how to make LLMs more structured, working at Thrive, and more

Jackson Dahl

and

Linus Lee

Aug 04, 2025

I was introduced to Linus about 18 months ago, and had one of those rare coffee meetings that leaves you with ideas that sit in your head for weeks and months to come.

He explained his metaphor for technology (that I’ve referenced elsewhere) that frames tools on a gradient of maps to turn-by-turn navigation (and ultimately to self-driving cars) with regard to how much complexity and agency they give us. Some tools expose us to more details, others just get us to where we want to go. He also shared this great talk on “liquid art” that I still think holds truth for how people will create with AI.

I didn’t stay in particularly close touch with Linus, but noticed he left his role at Notion to join Thrive Capital, a firm I deeply respect. Meanwhile, more recently, some of my research for my conversation with Geoffrey Litt reminded me of Linus, and Geoffrey similar praise for him.

Episode 21: Geoffrey Litt on Why Software Should Feel Like a Home Kitchen

Jackson Dahl and Geoffrey Litt

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So here we are, full circle, with a conversation that continues with some themes from my discussions with Geoffrey, Anjan Katta, Steph Ango, and others. Beyond this, Linus is one of the most creative and rigorous thinkers (and makers) when it comes to building real tools with LLMs, and he approaches technology, design, and engineering from a fundamentally human-centric standpoint. The future truly is us to up to shape. I hope you enjoy!

Dialectic Ep. 24: Linus Lee - Engineering for Aliveness

Dialectic Episode 24: Linus Lee - Engineering for Aliveness - is available on Spotify, Apple Podcasts, and YouTube, and all podcast platforms.

Linus Lee (Website, X) is a builder, engineer, and writer who explores how software can amplify our abilities, humanity, and agency. He builds, researches, and advises on AI at Thrive Capital, a venture capital firm, and continues to write and hack on personal projects.

Previously, Linus held research or engineering roles at Notion, Betaworks, Replit, and others, and has built over 100 personal projects on the side--including his own programming language and most of the tools he uses day to day. Most of his work, writing, and projects revolve around language, knowledge work, thinking tools, machine intelligence, and latent space for creativity.

We begin with how technology can concentrate or distribute power and amplify our diminish our agency. Then he breaks down his framework around instrumental and engaged interfaces, why representation is so critical in tools, and talks through what 'tools for thought' actually means. We also discuss the state of LLM tools and how they can become more robust, as well as how latent space could be codified to help us understand more qualitative domains. This bleeds into his approach to and work at Thrive, which we discuss in detail.

Linus is attuned to the ways technology can make us more or less human, and that's reflected throughout. Technology is not determined: the future we imagine and create is entirely up to us. Will we optimize ourselves into something non-human, or dream our way into something beautiful?

Views expressed here are the interviewee's and not intended as investment advice.

Timestamps

(2:23): Values and Technology as an Amplifier for Agency
(9:57): Instrumental vs. Engaged Interfaces and Tools
(20:05): Representations, Abstraction, and Exposing Complexity
(33:23): Dreaming of Thinking Tools, Especially Beyond Text
(48:06): LLMs, Mechanical Thinking, and Going Beyond in How We Understand
(57:42): Embeddings of People
(1:01:16): Applying Rigor and an Engineering Approach to Working with LLMs
(1:08:26): Collaborating with AI: Having Agents Work for You vs. Accelerating Your Craft
(1:11:10): Using LLMs to Explore Latent Space
(1:14:58): Working at Thrive: building internal tools and taking software seriously at a VC firm
(1:28:09): What Great Engineering in an Organization Looks Like
(1:33:50): Humanity, Aliveness, and Technology
(1:39:41): Dreams, Aesthetics, Imagery, and Intentionally Guiding Technology
(1:46:09): Lost to Wonder