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24: Linus Lee - Engineering for Aliveness
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.Full transcript and all links are available at ⁠⁠https://dialectic.fm/linus-lee⁠⁠Timestamps:(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 WonderReferences⁠⁠What are conference talks about? - Linus⁠⁠⁠⁠Instrumental interfaces, engaged interfaces - Linus⁠⁠⁠⁠What makes a good human interface? - Linus⁠⁠⁠⁠Dialectic Ep. 21: Geoffrey Litt - Software You Can Shape⁠⁠⁠⁠Linus Lee on Representations for MIT Media Lab Lecture⁠⁠⁠⁠On Exactitude in Science - Jorge Luis Borges⁠⁠⁠⁠C. Thi Nguyen⁠⁠⁠⁠The Three-Body Problem - Liu Cixin⁠⁠⁠⁠The British Library⁠⁠⁠⁠Spatial Interfaces - John Palmer⁠⁠⁠⁠Prism: mapping interpretable concepts and features in a latent space of language - Linus⁠⁠⁠⁠Synthesizer for thought - Linus⁠⁠⁠⁠Liquid Art - Kate Compton⁠⁠⁠⁠Thoughts on Loom - Linus⁠⁠⁠⁠Linus on Flora⁠⁠⁠⁠Story of Your Life - Ted Chiang⁠⁠⁠⁠Arrival (2016)⁠⁠⁠⁠Linus's bio, culinary edition⁠⁠⁠⁠Goodfire AI⁠⁠⁠⁠Notion, AI, and Me - Linus⁠⁠⁠⁠Dan Shipper⁠⁠⁠⁠Every⁠⁠⁠⁠Philip Wadler⁠⁠⁠⁠Create things that come alive - Linus⁠⁠⁠⁠A Rant about "Technology" - Ursula Le Guin⁠⁠⁠⁠Radio City - Linus⁠⁠⁠⁠Linus tweet on aesthetics⁠⁠⁠⁠Wonder engines - Linus⁠⁠⁠⁠Seeing Is Forgetting the Name of the Thing One Sees - Lawrence Weschler⁠⁠⁠⁠lost to wonder⁠⁠Dialectic 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
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23: Tamara Winter - Tacit Trust & Caring Curiosity
Tamara Winter (X) is the Commissioning Editor of Stripe Press, where she exercises her taste to identify the knowledge and "ideas for progress" that matter most in alignment with Stripe's mission: to increase the GDP of the internet."Tammy" worked at the Charter Cities Institute and the Mercatus Center at George Mason University, which is chaired by Tyler Cowen. Tammy is obsessed with tacit knowledge and the illegible parts of the world that actually support so much of our lives, work, and societies. This includes taste, charisma, relationships, and a wide-range of load-bearing infrastructure that supports healthy and trustful societies, from small-talk and manners to hidden forces that prevent anti-social behavior and maintain safe places to live and work.We discuss this and more, including how she selects the ideas worthy of Stripe's audience, her unique career path, her refreshing take on agency, her standards for herself, reading and writing, and how she chooses how to spend her time. Above all, Tammy's incredible love of other people shines throughout the conversation.Full episode transcript with all linked references: https://dialectic.fm/tamara-winterTimestamps2:09: Taste, absorbtion, and influences10:54: Deploying your taste15:49: Ideas that matter and taking yourself seriously22:13: Aesthetics24:16: Choosing Teachers and Authors28:15: Charisma & delightfullness privilege34:59: Living a relational life44:07: Trust, social scaffolding, and small talk51:01: Erosion of social norms, low-trust environments, and load-bearing infrastructure1:02:17: Cultural arson and the dark sides of "you can just do things"1:15:44: The healthy kind of agency1:20:45: Tammy's N-of-1 path and who she aspires to rhyme with1:28:38: Red herrings of success and focusing on outcomes1:32:22: Assortive everything1:37:52: Personal and professional standards1:43:06: Journaling, great writing, and audience1:57:29: Reading & BiographiesKey Links:The Art of Doing Science and Engineering - Richard HammingOn Self-Respect - Joan DidionScaling People - Claire Hughes JohnsonHigh Growth Handbook - Elad GilVirginia Woolf on MontaigneAva on TammyOld Enough!Sort By Controversial - Scott Alexander (Scissor Statements)Scarf tweetTammy's advice to young peopleAn Elegant Puzzle - Will LarsonInteractThe Making of Prince of Persia - Jordan MechnerFrank Sinatra Has a Cold - Gay TaleseWhy not inquire together more? - Tyler CowenThe Common Reader - Henry OliverIn Five Years - Rebecca SerleWalt Disney: The Triumph of the American Imagination - Neal GablerUp from Slavery - Booker T. WashingtonAnna: The Biography - Amy OdellThe Rise of Theodore Roosevelt - Edmund MorrisBrian JacquesA Pattern Language - Christopher W. AlexanderDialectic 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
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22: Nadia Asparouhova - Ideas that Infect
Nadia Asparouhova (Website, X, Substack) is a writer and researcher who has spent much of her career in service of the question: 'what's happening here?' across various parts of the internet.Nadia recently published her newest book, Antimemetics: Why Some Ideas Resist Spreading. She explores why consequential ideas, unlike memes and supermemes, fail to spread. She also recounts the last several years of online public and private life and how we're all less naive than we were in previous eras of the internet. Critically, she suggests a path toward poking our heads out of group chats and silos to engage in publicly discussing or promoting the ideas that matter most.Her first book, Working in Public: The Making and Maintenance of Open Source Software, was published by Stripe Press. Nadia also worked at Substack, Protocol Labs, and Github, and has written extensively on Silicon Valley Culture; the importance of ideas and institutions; consciousness, attention, and meditation; and more.Nadia's self-described sweet spot is when people respond to her writing by saying,"I read this piece and it gave me words for a thing that I didn't know how to express before." I can attest that is true, both for Antimemetics and for much of her other thinking. And as much as she writes about ideas, I admire how focused she is on how they might produce action.Nadia believes that important ideas infect us, and the reasonable response to that is to be tremendously thoughtful about our attention. I hope this conversation inspires you to put great care into where your attention goes.Transcript and all links: https://dialectic.fm/nadia-asparouhovaTimestamps:1:31: Why Ideas Matter9:33: The Last 10 Years of the Internet and Attention Collapse17:07: How The Internet Caused Attention Collapse19:59: Private Coordination in Public Spaces24:01: Legibility and Illegibility as a Tactic28:28: Ideas Are Not Created Nor Discovered; They Infect Us35:17: Defining Antimemes42:00: Ideological Black Holes: Supermemes49:13: Engaging in the Public Square vs. Opting Out54:16: Truth Tellers who Can Bring Anti-Memetic Ideas to Light1:05:06: Champions, or the Great Apostle Theory1:10:57: Institutions, Ideologies, and Movements1:24:51: Attention1:31:30: Jhanas1:38:42: Writing a Book1:46:19: Connecting the Dots in Reverse1:50:29: Lightning Round: Fighting (or Working With) Human Nature, Software as Passion Project, Democracy, Space Away from the Center of ThingsDialectic 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
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21: Geoffrey Litt: Software You Can Shape
Geoffrey Litt (Website, X) is a designer, engineer, writer, and researcher at Ink & Switch, where he champions malleable software: the idea that ordinary people should be able to mold the digital tools they rely on every day. Ink & Switch is an independent research lab focused on how computers can help us think and work. While researching and writing, Geoffrey and team also build products and prototypes to explore how their ideas can exist in practice. Geoffrey got his PhD at MIT CSAIL, where he built on his inspiration around computational media like spreadsheets, hoping to push more software toward the ethos of end-user programming, but without the technical complexity. In a sense, why should using software and changing it be any different? Previously, he built software for teachers at Panorama Education, which he joined out of school as one of the first employees.Geoffrey and collaborators recently published a definitive piece on malleable software and we discussed it in detail. We dig into why most modern apps feel like sealed boxes rather than flexible tools and environments, and what changes when your app, document, or workspace, feels more like Lego than machinery. Geoffrey makes his case that we want software tooling to feel like a chef knife, not an avocado slicer, and we talk about how the best designed tools help users up a smooth slope of learning and ability. He argues in favor of deeper understanding, illustrated by one of my favorite ideas: The Nightmare Bicycle. We talk about how LLMs are enabling malleable software and how local tinkerers might be able to build systems for themselves and their team or communities that understand their needs more deeply than any professional designer could. Finally, Geoffrey lays out a call to arms for founders: build products that treat users as co-authors who understand their own needs, not just consumers.On one level, this is a conversation about software and design. But it is really about agency. I hope it inspires you to pop open the hood on various aspects of your life, look at what's inside, and trust yourself to tinker. As Steve Jobs said many years ago, "the minute you can understand that you can poke life, and if you push in, then something will pop out the other side; that you can change it, you can mold it—that's maybe the most important thing."All links and transcript: https://dialectic.fm/geoffrey-litt---This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net worths of $1M-100M to create its 2024 Wealth Report. They asked about financial goals, spending habits, how much founders themselves, investment portfolio breakdowns, risk tolerance, estate planning and philanthropy, and more. Visit https://joinhampton.com/community to access the report.---Timestamps2:12: Agency in a Digital World and Geoffrey's Creative Medium: Software12:17: Intro to Malleable Software20:42: "Popping Open the Hood" & The Nightmare Bicycle: A Case for Understanding How Systems Work27:47: Computational Media, Spreadsheets, and Digital Informality34:01: Legos and Home Cooking as Metaphors for Software42:30: Two Types of Malleable Software: Modular-by-Design and Hacking48:35: Hampton50:13: Designing for a Smooth Slope58:20: Unbundling Apps into Environments and Tools1:17:58: Why Do the Work at All When AI Can Do It? When Should We be in the Details?1:29:22: Empathy & Design: Enabling "Local Developers" Who Know Their and Their Community's Needs1:38:23: A Case for Optimism About Human Agency1:51:09: AI's Impact on Malleable Software1:59:03: Commercial Incentives and Ecosystem Change2:04:17: Research and Ink & Switch2:11:46: ChatGPT as a Muse2:15:34: Working at MUBI and Solving the "Too Many Things to Watch" Problem2:18:27: Japan's Culture of Care2:22:15: Mastery and Variety2:24:34: Joy and Clarity as a Parent2:25:30: Expressing Care Through What we Make
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20: Yancey Strickler - Constellations of Creativity
Yancey Strickler (Website, X, Metalabel) is a writer, entrepreneur, creative, and founder of Metalabel, a network and platform that allows creative people to release work together. He is also a board member, co-founder and former CEO of Kickstarter and is currently working on establishing a new kind of corporate structure, the Artist Corporation.Yancey's life and work has revolved around what it means to be a creative individual, and how to improve the cultural and mechanical forms that enable artists and creatives.We talk about how much of modern society is rooted in individualism, how that wasn't always the case, and how the internet is evolving our sense of self. We get into creativity, the term's surprisingly recent origins, and why Yancey believes the 21st will be the "Creative Century." Then, we go beyond the individual and discuss the deeply-rooted longing that all of us have to be a part of something bigger than ourselves. Yancey suggests that is not simply about being subsumed by a collective, but by maintaining our individual star while becoming part of larger constellations—like the labels that have empowered the distribution of ideas for centuries. Finally, we discuss the forms Yancey has or is helping to build and imagine a future where even more of the world creates professionally.May we all shine more brightly and find others who inspire us to make wonderful things.Full transcript and all links available at https://dialectic.fm/yancey-strickler.---This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net worths of $1M-100M to create its 2024 Wealth Report. They asked about financial goals, spending habits, how much founders themselves, investment portfolio breakdowns, risk tolerance, estate planning and philanthropy, and more. Visit https://joinhampton.com/community to access the report.---Timestamps1:41: Individualism, Identity, and the Internet 19:13: Creativity — Its Origins, Art, and Reaching Toward Something Deeper 33:30: The Creative Century and a Case for the Continued Growth of Professional Creativity 38:27: Hampton 40:02: Something Bigger than Ourselves — The Post-Individual, Bentoism, Being a Star and a Constellation 51:51: Labels & Conspiring Together in Practice 1:07:15: New Forms & Kickstarter 1:18:44: Metalabel 1:31:56: Creativity and Commerce & A Brand New Form: The Artist Corporation 1:46:22: The Long Game: Supporting the Artistic and Creative LifeKey Links & References (all available at dialectic.fm)YOUTH MODE - K-HOLEAdam Curtis on the dangers of self-expression - Yancey Strickler for The Creative IndependentInventing the Individual - Larry SiedentopThe WEIRDest People in the World - Joseph HenrichThe Second Self - Sherry TurkleDolly Parton memeNine Creative Meditations - YanceyThe Cult of Creativity - Samuel Weil FranklinThe Post-Individual - YanceyBentoismThe dark forest theory of the internet - YanceyThe Dark Forest Anthology of the InternetOur Band Could Be Your Life - Michael AzerradIntroducing MetalabelNew Creative Era with Yancey & Joshua CitarellaArtist CorporationsHow to long game - YanceyDialectic 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
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