Dialectic

David Senra (Website, X) is a podcaster and loves that title more than anyone. He hosts Founders, where he teaches the lessons of history's greatest entrepreneurs by way of the biographies he reads of them. This week, he launched a second show, David Senra, where he talks to the greatest living entrepreneurs (often about the lessons from Founders). The first episode with Spotify Founder & CEO Daniel Ek is available now, and the show is in partnership with Scicomm Media, the team behind Huberman Lab.David is an enthusiast about four things: entrepreneurship, reading, history, and podcasts. His two shows are the articulation of those obsessions in a form of service for the rest of us. He is following Charlie Munger's advice: "take a simple a idea and take it seriously."David is one of the most energizing people I've ever met and has greatly inspired my work. I've had several multi-hour conversations with him that left me buzzing afterward, and I'm pleased that this is no exception. We cover many of his favorite lessons and founders, his process, biographies, focus, fear, endurance, service, and legacy. I hope you are inspired to commit yourself to something worth your days and years.Transcript and extensive linked references: https://dialectic.fm/david-senraSpecial thanks to Josh Kale for producing this episode. Please check out his show Limitless on frontier technology and AI.Timestamps:(0:00) - Open(1:49) - Intro(3:02) - Podcasts are Energy Transmission(7:52) - People Buy Simple Stories(12:38) - Repetition Doesn't Spoil the Prayer(16:11) - Trust in Brands and Products (and Podcasts)(19:40) - Continuous Improvement and Speaking to a Moving Parade(26:18) - Confidence and Simplicity(34:55) - What Makes a Great Biography and Biographer(42:17) - Humanity in Context: Why Biographies are So Practically Helpful(48:52) - Fear(54:32) - Self Reflection and Commitment(1:06:52) - Considering Stuff Beyond Podcasting(1:10:40) - Focus and Making Time for Relationships(1:14:00) - What Should David Delegate?(1:24:36) - Advice for 2017 David(1:28:21) - Storytelling and Clear Thinking(1:32:19) - Defying Rationality and Creating Magic with Obsessive Details(1:38:09) - Self-Deception and Understanding Who You Are(1:45:01) - Intuition(1:48:34) - Being Easy to Interface With(1:52:26) - Biography Most Founders Would Benefit From: James Dyson's Against the Odds(1:57:05) - Simplicity and Edit Before You Make(2:02:42) - Lesson for Tech People: Learn from History(2:06:14) - What David Hopes His Kids Say About HimDialectic 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

Billy Oppenheimer (Website, X) is a researcher and writer who works closely with Ryan Holiday and Rick Rubin, and publishes the “Six at 6” newsletter. Billy is also working on his first book, The Work is the Win.We kick off by discussing one of my favorite new ideas: "looking for clues," a process and philosophy for creativity that Billy learned from Rick Rubin. He shares the story Rick told him when he learned and adopted this language, which is so representative of how Billy (and I!) research in our work.From there, we talk about Billy's robust research process and how he has created an external brain of the ideas and patterns that inspire him rather than relying on memory. We also talk about the importance of time as a filter and a series of maxims that underpin his work and creativity. We discuss the importance of inputs over outputs and his big idea and book title, "The Work is the Win," as well many related ideas on success, complacency, compounding, standards, initiative, local maximums, and more. We finish with some lessons from Billy's favorite people.This conversation is a field guide for making things, pushing through the messiness of progress, and attuning yourself to the richness of the world that often takes the shape of clues.Full transcript and all links: https://dialectic.fm/billy-oppenheimerTimestamps:0:00 - Intro 1:20 - Looking for Clues with Rick Rubin 17:42 - Billy's Own Clue-Seeking 24:26 - Balancing Listening to the Market and Finding Unique Influences 31:17 - Memory, Notecards, and Billy's External Brain 37:13 - Making Notes for an Ignorant Stranger, or Leaving Clues for Your Future Self 45:09 - Lingering and Time as a Filter 52:51 - Billy's Book and Big Idea: "The Work is the Win" 1:00:07 - Be Great Regardless 1:04:31 - Following Up Even When Your Abilities and Standards Don't Match 1:10:10 - Fending Off the Wolf at the Door1:15:55 - Unfolding and Planting Seeds 1:18:17 - Taking Initiative and Opening Doors: "He Who Hesitates is Lost" 1:24:58 - Stupid Bravery and Getting Past the Sewage 1:30:16 - Local Maximums and Resisting Personal "Folklore" 1:36:14 - Some of Billy's Favorites: Ryan Holiday, Rick Rubin, Steve Jobs, John Mayer, Greta Gerwig, Jerry Seinfeld, Ralph Waldo Emerson 1:56:45 - Side Quests 2:02:26 - "I Know What We Do Here" and Creative Environments 2:05:28 - Bringing Familiar and Unfamiliar Together 2:09:26 - Mastery and Compounding 2:12:44 - The Real Life of Appearances 2:15:43 - "Ton-goo-ey" and The Gifts We Give Ourselves Links:‎McCartney 3, 2, 1 (2021)The Way of the Tracker: The Path of “not this” - Boyd VartyEddie Murphy Is Tracy Morgan's Favorite | Comedians In Cars Getting CoffeePoetry UnboundWhen We Cease to Understand the World- Benjamín LabatutFill Up To Pour Out - Billy OppenheimerThe Subtle Art of Not Giving a F*ck - Mark MansonThe Psychology of Money - Morgan HouselLeBron James shows off photographic memoryThe Notecard System - Billy OppenheimerRobert GreeneMike Nichols: A Life - Mark HarrisThe Journal of Eugene Delacroix - Lucy Norton19. Henrik Karlsson - Cultivating a Life that Fits - DialecticStadium of selves — Steph Ango8. Steph Ango - Tools for Amplifying Our Light - DialecticThe third chair - Henrik KarlssonSecrets of the Creative Brain - Nancy AndreasenSetting down the snow globe - Jackson DahlBilly on RESTFace it: you're a crazy person - Adam MastroianniTennessee Williams – The Catastrophe of SuccessCritique of Pure Reason - Immanuel KantBilly on Constraint, Gide, and Kant's Dove‎There Will Be Blood (2007)The War of Art - Steven PressfieldBilly on unfoldingHe who hesitates is lost - Joe Rogan & Jordan PetersonUnfolding - Henrik KarlssonBilly on John Mayer, HubermanSteve Jobs on folkloreThe Making of Prince of Persia - Jordan MechnerMake Something Wonderful - Steve Jobs‎Lady Bird (2017)‎Frances Ha (2012)Billy on Greta GerwigBilly on "I know what we do here"The Art Spirit - Robert Henri

Maxwell Meyer (X, Newsletter) is the founder and editor of Arena Magazine, an "American Propaganda" print and digital publication focused on technology, capitalism, and civilizational progress. Max also works with Joe Lonsdale at 8VC and is the proprietor of his Iowan farm, Henry Hills. He was previously the editor of the Stanford Review.Our conversation is about ideas Max is most interested in across storytelling and media, American values, technology and progress, capitalism, writing and craft, and deep love for his country.We start with critique, the media's tendency toward cliché, and defending the new while building trust with readers. Then we talk about American ideology: its radical founding myth, collective enterprise, and a nation of movers. Max makes a case that national character ought to be lived and formed bottom-up, and repeatedly argues that cultural pendulum swings are as old as time and we need not overreact to the swings of the day. He describes tech's brief abandonment of the rest of America and talks through how we might export Silicon Valley's outcome-oriented culture to government and other industries. Max argues that the foundation of capitalism is simple: "you can't kill your counterparty." We of course discuss Arena, magazines, writing, editing, and his ambitions there too.Above all else, Max makes the case for America, big and small: the beautiful, always-changing, rarely-agreeing, perpetually striving amalgamation of souls that stretch from sea to shining sea.You can subscribe to Arena here: https://arenamag.com/subscribeFull transcript and all links: https://dialectic.fm/maxwell-meyerTimestamps:00:00: Intro01:14: Elon, The Media, Cliché, American Collectivism, and Cultural Pendulum Swings09:07: Media, Criticism, and Defending the New17:49: American Ideology: The Declaration, Communal Enterprise, Americans as Movers28:20: Patriotism33:36: Learning from the Rest of the World40:27: A Case for Progress49:38: Tech's Separation from American Culture in the 2010s58:44: Tech Accountability and Engaging Normal People on their Premises1:15:23: Silicon Valley's Tiny Nations and Alex Karp's "The Technological Republic"1:21:19: The Frontier and the Core: Exporting SV Engineering Culture to Government1:28:46: Principled and Unpredictable Thinkers1:34:06: The Case for Capitalism1:43:07: Defending Critiques of Capitalism and Concerns of Concentration of Power1:49:37: Arena, Good Writing and Editing, Magazines as a Medium, Durability, Influences2:02:19: Big and Small America2:06:16: Joe Lonsdale2:06:50: Upholding Abundance2:11:39: Cooking and Bringing People Together2:12:38: The Back Half of the Brain2:14:02: The Places Between PlacesKey Links:The Man-Made Miracle of SpaceX - Max MeyerMax Meyer Launched a Print Magazine in 2024. Here’s Why. - Infinite Loops PodcastMan in the Arena SpeechDemocracy in America - Alexis de TocquevilleAmerica against America - Wang HuningHow United Became an Airline - Wall Street JournalThe Gentle Singularity - Sam AltmanPlaying With Guns (and Phones) - Nadia AsparouhovaThe Emerging Democratic Majority - John B. JudisA Techno-Republic, If You Can Keep It - Maxwell MeyerThe Tinkerings of Robert Noyce - Tom Wolfe | EsquireBrian Schimpf: Engineer at War - Maxwell MeyerTo Save America, Restore Our Frontier - Joe LonsdalePalantir’s Alex Karp Talks About War, AI and America’s Future - NYTThe Earthly Miracle of the Grocery Store - Maxwell MeyerA More Perfect Mediocracy - Leo LeibovitzMeditations On Moloch - Scott AlexanderThis is Water - David Foster WallaceCalifornia SublimeThe Magic Water of Hot SpringsWelcome to the MAGA Hamptons! - Max Meyer | The Free PressThe Green Counter-Revolution - Max MeyerHow To Kill A Country - Samantha PowerI Bought an Iowa Farm at Age 22 After my Brother DiedPlaces Between PlacesDialectic with Jackson Dahl is available on all podcast platforms.Follow ⁠Dialectic on Twitter⁠Follow Dialectic on Instagram

Mackenzie Burnett (Website, X) is the co-founder and CEO of Ambrook, financial software for independent businesses starting with farms and ranches. We trace her arc from a policy-first upbringing (USDA household, Congressional internships, climate-security research at Stanford) to a building software for rural America. We talk about why Mackenzie loves America and cares about agriculture, the challenges of aligning sustainability with business and government, and pragmatically building resilience. Mackenzie talks about the American Dream and why independent small businesses are the foundation of it in many ways.Then we get into Ambrook’s product philosophy: why “all roads lead to accounting,” how multi-P&Ls and biological inventories make farms deceptively complex, and why understanding bookkeeping and money movement enables better decision making and understanding over the long run for big and small businesses.We also talk through Mackenzie's broad ambition for Ambrook; her growth as a leader; brand, aesthetics, and environment; Ambrook's editorially independent research division, Offrange, and more. Mackenzie is one of the most quietly ambitious and focused people I've met, and yet under her impressive and serious exterior is a life and love for America and its people that is all heart.Special thanks to Josh Kale for his help producing this episode.---Full transcript and all links: https://dialectic.fm/mackenzie-burnett---Timestamps00:01:11 Intro00:02:51: The American Heartland00:05:21: Agriculture, Policy, and Government00:12:29: The Challenges with Prioritizing Climate Risk: "Long Term and Abstract"00:18:04: Pragmatic Environmentalism and Resilience that Drives Business00:21:49: The American Dream00:25:52: The Importance of Independent Small Businesses00:28:58: Entrepreneurship on the Frontier: America's First Entrepreneurs and Ambrook's First Customers -- Farmers00:36:28: Biological Factories: Why Farms are Complex Businesses00:40:41: Why Everything Goes Back to Accounting00:44:30: Why Money Movement Matters00:51:13: Ambrook as a Twenty-Year Container00:57:27: The National Importance of Agriculture01:00:49: The Features of Illegibility01:04:49: Ambrook's Long Term Vision01:10:17: Making the Intractable Tractable (And Doomscrolling Your Company's Slack)01:14:42: De-Risking and Becoming Friends with Anxiety01:17:26: Building Something That Takes on a Life of its Own01:20:07: Ambrook's Culture in Three Words01:21:26: Brand and Storytelling01:26:11: AI Enabling the Middle Class01:30:57: California History and J.G. Boswell01:34:05: Niche Subjects and History and "The Land Where Lemons Grow"01:36:46: Disney's Magic Band01:39:15: Strange Math and Happiness and Sadness in Parallel01:41:31: Aesthetics, Beauty, and Physical Design Systems01:47:31: The Draw to Start ThingsLinks & ReferencesAmerica, the Beautiful - Mackenzie BurnettThe Founder's Letter: Mackenzie Burnett, AmbrookDisposable CamerasA “precariously unprepared” Pentagon? Climate security beliefs and decision-making in the U.S. military (Mackenzie's Thesis)The Land Where Lemons Grow - Helena AttleeDubai Chocolate Made Pistachios Viral, But Are Small Farmers Winning? - Offrangesam altman: “honestly, i feel so bad about the advice i gave while running YC i’ve been thinking about deleting my entire blog”affinity - AvaLunch with the FT: Novak DjokovicAmbrook Series A AnnouncementOffrange (Fka Ambrook Research)AI Could Actually Help Rebuild The Middle Class - David AutorThe King of California - Mark Arax | GoodreadsTulare LakeTweet on The Land Where Lemons GrowMagicBandLeaders in TechInteractJane JacobsFrom plows to platforms: how Stripe is powering modern agricultureDialectic is available on all platforms:Follow ⁠Dialectic on Twitter⁠Follow Dialectic on InstagramJoin the ⁠telegram channel for Dialectic⁠Subscribe to Dialectic on YouTube

Cyan Banister (Website, X, Substack) is an investor, artist, and co-founder and General Partner of Long Journey Ventures. Previously, Cyan spent four years at Founders Fund and has a legendary angel investing track record alongside her husband, Scott, including early rounds in SpaceX, Uber, and DeepMind.Cyan is as original as they come: she grew up on a Navajo reservation and was homeless by 15, with a series of unlikely serendipitous moments combined with optimism, agency, and love of capitalism taking her to a very different life than the one she grew up with. I focused this conversation not on Cyan's work, but her unique approach to living.We begin with Cyan’s “church”: a weekly visit to see Bobby McFerrin and co. do live, jazz acapella in Berkeley, CA. We discuss how this space ties to presence, openness, and play, and then talk about the tension between novelty and consistency as she continues on her own path toward self-love and mindfulness. She also tells me about her radical approach to accountability and the empowering results of assuming that everything is her fault.One of Cyan's favorite words is the French dérive, or an intentional drift, and it embodies her approach to the world. She moves with childlike wonder, seeking to see things and people from new perspectives and challenging others to react beyond their default settings. She daydreams about the outcomes she wants and has remarkable conviction and faith even when others do not believe her.We wrap with a grab bag representative of Cyan's diverse interests, from filmmaking and performance art to the US Constitution to Bill Murray. Cyan manages to combine randomness and intentionality, naiveté and sober-minded awareness, humility and conviction. I hope you are are as inspired as I am to live more playfully, seriously, and courageously.Full transcript is available at https://dialectic.fm/cyan-banisterTimestamps0:01:23: Intro0:03:45: Cyan's "Church"0:16:21: Stillness, Mindfulness, and Introspection0:28:47: Learning to See in Original Ways0:39:38: People: When the "Light is On," "Collecting Minds," and Conjuring Friends0:46:55: Cultivating Childlike Joy and Refusing to be a Victim0:52:30: Radical Accountability0:56:28: Randomness, Faith, and Experimentation1:06:22: Conviction and Peter Thiel1:12:54: Returning to Seed Investing and Long Journey Ventures1:18:23: Thoughts on Art1:23:42: Performance Art1:26:37: Cyan's Creative Projects1:32:51: Boredom1:36:06: Living Around Elderly People1:42:14: Pete Buttigieg1:45:57: Being a Role Model1:48:26: Young People's Future1:52:46: Scott Banister and Lessons for Her Kids1:55:35: "It Just Doesn't Matter" And Who Pulls the StringsKey LinksCyan - by Kevin Gee and Dan Scott - Cloud ValleyCyan Banister — From Homeless and Broke to Top Angel Investor - Tim FerrissInvesting for a Higher Purpose - Invest like the BestBobby McFerrinUniversity of Texas at Austin 2014 Commencement Address - Admiral William H. McRavenExample of Motion and Bobby's performanceThe Magic Glasses - Frank HarrisMy Life and Loves - Frank HarrisLee JacobsBILL MURRAY TALKS ABOUT THE PAINTING THAT SAVED HIS LIFEThe Diamond Age: Or, a Young Lady's Illustrated Primer - Neal Stephenson | GoodreadsIt Just Doesn't Matter! - Meatballs (1979)‎The Razor's Edge (1984)Bill Murray gives a surprising and meaningful answer you might not expect. (Charlie Rose)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

Reggie James (Substack, X) is a designer, writer, and entrepreneur. Reggie previously founded Eternal and recently edited and published Hardware 2024, a book highlighting recent attempts at creating a different hardware future. This conversation happened live on stage at FWB Fest 2025 in Idyllwild, CA.We explored Reggie's frame of technology as a mirror and the Kevin Kelly-inspired notion that technology has an agenda of its own. Reggie has a fresh perspective on brand and "feel" as they relate to technology products, why friction can create meaning, and a Naoto Fukasawa-influenced view that design is about communicating values. The latter, for Reggie, originates with writing.We dipped into a discussion about how hardware and how it shapes our software cultures, and what a world with more basic luxuries like the iPhone might look like. We also discussed "loaded" technologies and the current narratives that are working in crypto vs. what might be idealized.The conversation concludes with a zoomed out meditation on myth, American western idealism, personal history, and what type of vision is required to create something radically new. This episode is shorter than usual given the live nature, but it's jam packed and I'm thrilled that we were able to cover a lot of ground across many of the ideas that are representative of Reggie.Full transcript and all links: https://dialectic.fm/reggie-jamesVideo version from FWB livestream available here.Timestamps3:05: Technology as Mirror8:04: De-fanging Loaded Technologies12:43: Writing's Role in the Design Process16:13: Affordances, Software, Hardware, and Values22:53: Universal Luxuries25:46: Friction and How Technology Can Make us Feel30:16: The Role Brand Plays in Technology Today34:30: Successful Narratives in Crypto41:30: Crypto as a Mirror44:39: American Myth & West47:56: Personal Myth54:16: VisionReferencesWhat Technology Wants - Kevin KellyCrying in the Garden ~ Closing Eternal - Reggie JamesJoan Didion on writing to thinkUniversals & Luxuries - Reggie JamesNaoto Fukasawa: Embodiment - Naoto Fukasawa THE TOKYO TOILET‎Perfect Days (2023)The Media Lab: Inventing the Future at M.I.T. - Stewart BrandThe Near Collapse of the American Myth - Reggie JamesThe Timeless Way of Building - Christopher W. AlexanderROLE: CREATIVE DIRECTOR || COMPANY: USA - Reggie James

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

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

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

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

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

Full transcript and all links: dialectic.fm/henrik-karlssonHenrik Karlsson (Substack, X) is an independent writer focused on "writing a few good essays." Two of them are among my most consistently recommended: on designing your life and finding your wife (or husband).Henrik's always written, but lived a winding path across software programming, music, poetry, biology, an art gallery, and other odd jobs. A few years ago, Henrik and Johanna picked up their life in Sweden to move to a small island farm in Denmark so they could homeschool their daughters. He now writes on Substack full-time and lives an unusual dual-life: one is remote and intimate; the other is connected and wide. My favorite theme of his writing is self-cultivation: introspection and action, designing a life that fits you by experimenting, how to think and how to learn, embracing being wrong and seeing past your blindspots, and living in concert with past and future selves.I also love his writing on relationships: how to find your life partner, why writing helps others see the inside of your head, how to use the internet as a serendipity machine for finding your people, teaching and parenting, and what its like to be around exceptional people who make your world bigger.He also writes about education, self-organizing systems, AI, exceptional childhoods, and more. But I find the topic rarely matters—all of his writing expands me. What a gift. I hope you enjoy the conversation as much as I did. May we all embrace the burden of freedom—freedom to iteratively unfold into a life we never could have imagined. If you enjoy the episode, please consider supporting Henrik's writing, as he is fully reader-supported.---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.---Timestamps2:36: Self-Cultivation, Introspection, and Larry Gagosian8:46: Writing to Think16:05: Using Strong Opinions as an Opportunity to Learn (and Willingness to Look Stupid)21:53: "Not That" vs. "Maybe this?": Creativity and Formulating a Positive Possible Future25:12: Self-Criticism and Kindness to Your Past Self and Ideas28:44: Eclectic Interests (Poetry, Programming, Music) and a Winding Path to Becoming a Writer Pulling on the Threads of "Dead Ends"33:10: Introspection, Agency and Being Sentenced to Freedom38:09: "Fit," Unfolding, Making Contact with Reality, and Designing Your Life with Experiments49:06: Seeing Past Blindspots and Listening to Feedback the World Gives Us1:04:16: The Role of Ambitious Goals in the Context of Unfolding1:10:06: Hampton1:11:41: Escaping Flatland and People Who are "Spheres": Meeting People Who Help You Expand What is Possible1:26:53: Asking Questions that Push People Past their Cache1:31:12: Embracing, Being Seen By Strangers, and Finding Your Corner of the Internet1:48:55: Ruthless Prioritization and Making Time to Get Better1:57:05: Initial Spark and Connecting with People2:05:58: Collaborating with Henrik's Wife Johanna2:09:46: Living a Barbell Life Inside and Outside of the Computer and Henrik's Scale of Ambition2:16:48: Sacrifice2:18:57: Pseudonymity and Playing with Identities2:20:57: Self-Organizing Systems2:22:51: Learnings from Homeschooling His Kids, Reading Adult Books with the 3-Year-Old, and Becoming a Mentor to Help Them Unfold2:33:13: Writers Who Help Us See Ourselves2:35:13: Writing and Thinking in Swedish vs. English2:37:44: Kindness and Gratefulness to Our Past Selves and Generosity to Our Future Selves – And Modeling That For OthersJoin the ⁠telegram channel for Dialectic⁠Follow ⁠Dialectic on Twitter⁠Follow Dialectic on Instagram

Tom Morgan (X, Substack) is a "curiosity sherpa," writer, and podcaster who runs The Leading Edge, a community for leaders focused on personal transformation and authenticity.I first encountered Tom and his ideas during his talk at Sohn on Iain McGilchrist, left vs. right brain, and curiosity. Tom writes about complexity, curiosity, and consciousness, and wades into the deep end of various topics that most of us would place in "woo," mystic, and spiritual territories. He spent most of his career on Wall Street and brings a scientifically-inclined, rationalist approach to researching and amplifying some of the most surprising modern and ancient ideas about the nature of humanity and the universe.With this conversation, I aimed to create a primer on Tom's writing, approach, and the ideas he returns to most. We discuss following your energy, how curiosity is a guiding force, complexity and emergence, and why the world is overrated toward left-brain rationalism. We explore practical questions—How do you know your gifts? When should you pivot or persevere? What does real exploration look like when the world offers no safety nets? And then we wade into much stranger, or even heretical ideas—at least for a modern, intellectual, western audience—including the notion that consciousness is much vaster than what we've come to understand, and how we are just a small part of a much bigger whole.I hope you enjoy the conversation and consider some ideas that are much more fringe than you're used to. I definitely left it with more questions than answers. And more than that, I hope you are inspired to attune yourself to your curiosity. Perhaps, you may even have the faith to follow that thread pulling you toward what appears today only to be a wall.Episode transcript.---This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net works 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.---Timestamps:2:03: Following Your Energy and Positive-Sum Games6:04: Curiosity and Complexity: Differentiation and Integration8:12: Entropy & Syntropy: Unpacking Curiosity, Love, and Desire12:34: Emergence and What All the Mystics Point to: Integration15:14: Left Brain & Right Brain: A Primer on McGilchrist's "The Matter with Things"28:58: Hampton30:34: Discovering Your Gifts37:35: Creativity and Sustaining Curiosity43:12: Life Pivots, Especially When You Aren't 2250:24: A Challenge vs. A Grind: When to Keep Going or Try Something Else56:19: Synchronicities1:00:58: Openness and Wisdom1:04:19: Error Correction, or Something Else?1:06:02: Tom's Mission and The Meaning-Mortgage Question: Can you really do what you love?1:08:45: Fear, Faith, Love, and Seeing Reality1:12:59: "Minimum Viable Woo" and Exploring Out There Topics with a Pragmatic Lens1:16:10: Stories1:18:51: Love, Emergence, and Intelligence Beyond Us1:22:52: A Looming Meta-Crisis, Global Consciousness, and Earth School: Blowing Out the "Woo" Rating1:33:41: Lightning Round: Pseudoscience as the Streisand Effect, Mystics, What Would Rattle Tom’s Worldview Most, Joseph Campbell, Fred Again1:40:41: Tom's Encouragement for His 20 Year Old SelfSelect LinksThinking the Unthinkable - TomExploring Gurdjieff's Mysteries - TomA Transformational Heresy? (Syntropy) - TomThe Matter With Things - Iain McGilchristTest Your Network - TomOur Unspoken Future - TomFred again.. Boiler Room: LondonTranscript and all references linked at https://dialectic.fm/tom-morgan.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

Alex Danco (Website, X, Substack) is a writer and Product Director at Shopify. Alex rose to prominence while writing his Snippets newsletter while at VC firm Social Capital in 2015. He wrote prolifically—about markets and financial systems, venture capital, startups, cities, culture, the technology-driven shift to a world of abundance, to name a few topics—through 2020, when he joined Shopify. Since then, he's had his hands full with Shopify and young kids, but recently published a flurry of new pieces on his blog while on paternity leave.This conversation starts with one of Alex's most insightful ideas: that a culture of gift-giving underpins technology, innovation, and creative work, and is the key to solving many of capitalism's coordination problems. We then talk about what businesses will look like in a world of abundance: AI agents, massive and accessible infrastructure, and where moats might actually lie. Alex shares why AI-enabled creativity may resemble musicians finding their sound and how and where we might find internet-native subcultures in 2025. Then he explains what "the medium is the message" actually means across different content formats and why audio continues to thrive. We wrap up with Alex's thoughts on the U.S and Canada as someone who identifies with both places and by taking a peek into some of the books that have most influenced his thinking.I've read Alex for years and I've always been impressed by how generative he is. That comes through in this conversation and I hope you are inspired to—like Alex—be more curious, creative, and most importantly, generous.Transcript and all links available at dialectic.fm/alex-danco.---This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more. Visit https://joinhampton.com/community to learn more and apply.---Timestamps:(0:00): Intro to Alex(1:28): Hampton(3:23): Steely Dan Intro(5:31): Coordination Problems and Silicon Valley(21:55): Girard, Taboos, Priests and Kings, and Magical Enzymes for Creating New Things(32:22): How Gifts Underpin New Things — Crossing Thresholds and Listening to Each Other(44:09): Gifts vs. Performance, Gifts vs. Slop(53:58): Overcoming “The Market for Lemons”: How Gifts and Market Mix and How Silicon Valley Resembles a Music Scene(1:02:29): Bubbles and Generosity(1:07:07): Patronage & Alignment(1:11:37): Coordination in Companies, O-Ring Problems, Michael Scott, and AI(1:25:51): Agency vs. Accountability(1:31:54): Wide vs. pointy businesses and What Makes a Platform(1:39:11): Moats, Leverage, and Figuring Out Your Sound: What Could Sam Altman Not Copy?(1:50:06): AI, Originality, and Creativity(1:55:15): Subcultures on the Internet and Frictionless Discovery(2:00:25): What Does "The Medium is the Message" mean?: Hot & Cool Mediums(2:11:57): Nixon-Kennedy Debates, Trump, Podcasts, Fox News, and the Decline of TV(2:25:21): Alex's Podcast Diet(2:28:52): U.S, Canada, and National Myths(2:44:23): The Most Influential Books on Alex(2:56:47): Learnings from Being in a Band(2:59:05): Scammers(3:02:55): Being a Dad(3:05:24): The Best Gift Alex Has Received and the Gift He Hopes to GiveAll references and links, with transcript.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

Anjan Katta (X) is Founder and CEO of Daylight, a new type of computer company.Having a conversation with Anjan is a bit like trying reign in a wild animal: his horsepower, wide-ranging philosophical interests, and unbelievable depth in the areas he cares about make him one of a kind. Fortunately, all of that energy is being channeled into his life's work, Daylight Computer Company. Daylight's mission is to build a computer that amplifies our humanity. That starts with Daylight's first product: The DC1, a tablet that combines the power and functionality of an iPad with the screen of a kindle. Anjan has been building Daylight for seven years across extensive research on screens and hardware, many near deaths, and mission-driven motivation.Anjan sees computers as a "magical medium" that we're in relationship with, unlike other tools. Unfortunately, "optimization of the means, yet confusion of goals" has led the technology industry to building hardware and software that sits in what he calls a "messy medium." With devices that can do anything and everything, they often fail to empower us toward the vision Steve Jobs called the bicycle for the mind.Throughout, Anjan and I discuss a philosophy toward life, career, design, and creating meaning that I hope will inspire you, whether you work on technology or not. May we all aim to get closer to ourselves and our humanity.---This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more. Visit https://joinhampton.com/community to learn more and apply.---Timestamps:(0:04): Hampton (1:57): Anjan Intro (3:54): A Bicycle for the Mind and The Computer: Tool or Medium? (13:15): The Core of the Computer as a Magical Medium: Relationship (16:39): The Waterslide/fall of Agency and Humanity as Nature's Generalists (27:35): What drove Anjan to Computers (33:00): Building the Non-Inevitable and Confronting Silicon Valley's "Optimization of Means, Yet Confusion of Goals" (39:25): Wandering Toward Daylight: a Computer that Doesn't Feel Like Other Computers (51:02): Is Daylight paternalistic? The messy middle and the Case Against "sporks" or Sh*tting Where You Eat (59:51): The Ultimate Messy Medium: The Phone as Our Main Relationship to the World and Starting Over with a More Simple Tool (1:08:04): A Magical Companion: The Primer, Dynabook, or "Hobbes" (1:13:31): Starting with Light(1:17:32): Daylight as "basically Just a Screen" & Applying "Lateral Thinking with Withered Technology" (1:28:18): High Resolution Decision Making: Designing with Intuition and Developing the Right Kind of "Feel" (1:40:24): The Four Dimensions of Daylight's Vision (1:58:08): Growing as a Person and a Leader (2:07:08): Growing Daylight the Company/Organism: Three Principles (2:12:42): Competition, Scaling Daylight, Why Someone Should Work There (2:17:45): Lighting Round: Paravel – Interactive Fiction App Developed for Daylight (2:19:54): The Evolution of Books (2:21:20): Most Influential Books on Anjan (2:23:43): Is AI making Us More Human or Less Human? (2:29:38): Boredom, Authenticity, and Integrity (2:32:06): Faith and Spirituality (2:33:04): What Anjan Has Learned from His Parents and What He's Forgiven Them For (2:34:38): Lilo and Stitch (2:35:50): The Most Important Thing All links and references and full transcript available at dialectic.fm/anjan-katta.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

D.A. Wallach (Website, X, Substack, Spotify) is an investor, musician, writer, and polymath. Today he co-runs Time BioVentures, backing frontier life-science and healthcare startups. Before that, he was an investor in in SpaceX, Spotify, Emulate, Beam Therapeutics, and Ripple, among others, and toured the globe as half of Chester French. He also released music as a solo artist and was Spotify’s first Artist-in-Residence.Our conversation moves from engineered serendipity—the art of a well-aimed cold email & surfing the web—to complexity science, the Santa Fe Institute, and what better systems might look like. We dive into markets and medicine: investing with a creative mindset; timing in biotech including CRISPR and GLP-1s; and the tension between free-market innovation and healthcare as a human right. D.A. unpacks how incentives shape everything from venture bubbles to hospital billing and how LLMs might move us closer to a universal standard of care.In the back half we talk creativity, beauty, art, and performance. We discuss whether AI makes us lazy or amplifies originality, DA's many lives across art, tech, and business, and end on his plea for artists to reclaim their throne of "cool". I hope you're inspired by D.A's combination of curiosity and depth and are reminded that you don't have to stay in one lane, regardless of how impressive it might be.Full episode transcript and all linked references available here.---This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more. Visit https://joinhampton.com/community to learn more and apply.---Timestamps:(0:04) Hampton(1:56) Intro to D.A.(3:29) Curiosity, Serendipity, and the Power of Cold Emails(9:21) Web Surfing & D.A.'s Potential One-Man Show(13:28) Learning to Go Deep: Explore vs. Exploit(19:18) Complexity Science, EO Wilson(29:20) What Makes Santa Fe Institute Special?(33:13) Complex and Bureaucratic Systems: How do you design a good system? And how do you change entrenched systems?(40:25) D.A.'s Attraction to Markets and the Fed Challenge(45:19) What Makes a Good Investor?(48:30) Creativity in Investing, Index Funds, Elon's Take on a Great VC, and Venture Capital's Real Customer(58:45) What Makes for Commercially Successful Creatives: Doing(1:05:24) Gene Editing & CRISPR, What "Early" Means in Biotech, and Isolating the Bet You're Making(1:12:48) GLP-1, Slow Burn Technological Innovation, FOMO, and Bubbles(1:18:49) Healthcare Incentives: The Tension between Free Market Capitalism and Healthcare as a Right(1:24:53) Patient Agency, LLMs, and Shifting Away from Paternalistic Doctors(1:29:02) Progress Toward a "Universal Standard of Care"(1:32:58) Artificial vs. Natural Intelligence(1:38:32) Should We Limit Technological Progress? D.A.'s Response to Alarm-Sounding: Focus on Today's Real Problems & Solutions(1:43:32) How Do You Keep Technology from Making You Creatively Lazy?(1:52:37) Performance, Fame, and Authenticity(2:00:27) Beauty As the Primary Motivation(2:06:17) Multiple Lives, Art vs. Tech & Business, and D.A.'s Plea for the Artists to Revolt(2:14:04) What Would D.A. Not Stop Doing for $1B?(2:15:41) Lightning Round: Anonymity, Tyler the Creator, Pharrell(2:20:04) African Studies at Harvard(2:22:08) Favorite Jazz Album(2:23:40) Finding New Music(2:25:08) LA: The Most Open-Minded City(2:27:16) What He Hopes to Teach His Young DaughterLinks (all available here)D.A. - Glowing (Official Music Video) Zero Toll MedicineModern Medicine Demands A Universal Standard of CareD.A. Live: "Feel" (Live From Capitol Studio B)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

Alex Zhang (Website, X, Instagram) is a cultural curator, community builder, and creative director. Currently, he's Chief Creative Officer of Powder Mountain, a where he's working with Reed Hastings to create a globally unique ski experience that combines art, architecture, and lots of fresh tracks.Alex loves people and curating spaces and experiences for them: whether that means parties, music festivals, or mountain towns. He joined Summit Series out of school, throwing large scale events around the world and working on Powder Mountain, a Utah mountain resort the ownership group had acquired. He then joined one of the first social DAOs, Friends with Benefits (FWB) as Mayor/CEO, after being tapped by its founder Trevor McFedries to scale the tokenized social club beyond a Discord Server. He launched FWB Fest, an annual in-person music festival and crypto conference with past performers including James Blake, Charli XCX, and Caroline Polachek. Most recently, he joined Reed Hastings to return to Powder Mountain after the Netflix co-founder acquired a controlling stake in the resort. Alex leads brand, art, architecture, and marketing.Blending culture, commerce, and "cool" is anything but a science, but Alex has made a career of it. I've known him for a decade and it's been a thrill to watch him continue to find strange intersections, blending worlds like music and tech, crypto and culture, and skiing and art. We talk about this, how to create spaces and events, living in the mountains, large scale art experiences, Christopher Alexander and Jane Jacobs, challenges in creating new cities, learning from Reed Hastings, and a life of deepening one's taste.I hope you enjoy and are inspired to life a more connected, playful, and present life.---This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more. Visit joinhampton.com/community to learn more and apply.---Full episode transcript and links available at dialectic.fm/alex-zhang.Timestamps(0:05): Hampton: Dialectic's First Partner (4:09): Commerce & Culture, Patronage, and Constraints (12:17): Curating People, Spaces, and Art: "Host Energy" (19:44): How to Throw a Party or Start a Scene (27:05): Unlikely Intersections and Authentic Marketing (35:36): Returning to Powder and Building a Unique Mountain Resort (42:31): Utah and Mountain Living (47:27): Randomness & Emergence: Christopher Alexander, Jane Jacobs, and Cities (52:24): Creating a Digital Feeling of Place (55:15): Network States and New Cities (1:00:42): "Community" (1:08:27): Organic Leadership Opportunities, Partnership, and Trust (1:15:12): Focused Leadership and The Power of Memetic Language (1:20:02): Learning from Reed Hastings as a Leader (1:29:09): Getting into Rooms and Finding Serendipity (1:32:58): Playfulness and Elon (1:36:25): Intuition and Career Decisions (1:39:10): Curating Music and a Life Goal of Refining Taste (1:42:56): Music's Role in Creating Great Spaces (1:44:08): Photography (1:46:02): Beginning, Learning to Ski and Scuba (1:48:10): Improving Los Angeles and What Makes it Special LinksPowder MountainFriends With BenefitsSummit SeriesHow Music Works - David Byrne‎Studio 54 (2018)Storm King Art CenterNaoshima IslandMarfa"The world is a museum of passion projects"Roden CraterChristopher AlexanderJane JacobsThe Network StateEdge CityEdge EsmeraldaWSA, a Manhattan Office Tower, Becomes an Unlikely ‘It’ BuildingRemedy PlaceWAREHOUSEWas That a James Turrell I Just Skied By?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

Nabeel S. Qureshi (Website, X, Substack) is a writer, entrepreneur, and former Palantir product lead known for his writing on technology, AI, Palantir, culture, and learning. After a brief hiatus writing and researching and spending nearly a decade at Palantir working across government, healthcare, and intelligence, he's now founding a new company.The first half of the conversation focuses on two big ideas. First: the growth of "slop" across media and culture and how "care" is its opposite. Then: how to think, learn, and understand more deeply across domains over a lifetime. We discuss how both of these sit against the backdrop of AI's rapid challenging of what it means to make and what it means to think.Then we discuss Palantir and "grey areas" that many technologists avoid working on or thinking about, government bureaucracy and DOGE, and how technologists are pursuing and accumulating power. We also chat about Nabeel's idea maze ahead of the new company, art and what it is for, and a range of other topics that showcase how curious, polymathic, and considerate Nabeel is.As the world changes at a breakneck pace thanks to technology and AI, Nabeel embodies a deeply humanistic approach that also accepts change as the default. This conversation inspired me to embrace surprise and strangeness, especially in creativity; to push through the friction and temptation to accept the answers at face value and instead yearn to more deeply understand; and to pursue a life of growth, practice, and care.Full transcript with all linked references available here.Timestamps:(3:21): “The Opposite of Slop Is Care.”(4:15): Defining Slop (14:17): Do We Decide What We Care About? (20:16): Original Seeing and Intimacy as a Path to Care (24:05): Creativity, Craft, and Care in the Digital World and Physical World (28:24): The Human Moat and Practice (32:48): Can AIs Care? (35:52): Understanding Things Deeply and “The Will to Think” (39:52): School: Getting the Answer vs. Deeply Understanding (41:44): High-Dimensional Learning from Simulations (Games) and Reality (the Real World) (48:38): Moving Down from Abstraction: Be Specific (50:49): Karl Popper, Fallibilism, Tyler Cowen, and Fighting Intellectual Inertia (53:00): Slowing Down (56:00): Nabeel's Funnel for Information & Retention (59:18): Spaced Repetition (Flashcards) (1:01:09): Palantir, Duty, and Engaging in Political and Moral Gray Areas (1:07:06): Palantir's Culture of Independent Thinking: People Who Speak Their Mind but Aren't Douchebags (1:09:38): Government Bureaucracy, DOGE, Power (1:14:51): Why Can't Governments Be Better at Error Correction and Healthy Renewal? (1:17:02): Technologists and Power (1:23:47): Nabeel's Next Company and the Idea Maze: “Context Is That Which Is Scarce” (1:27:11): Scientist Brain vs. Founder Brain and Context vs. Details (1:30:17): Tolstoy, Shakespeare, and What Art Is For (1:34:02): Art for Defamiliarization (1:36:00): What Makes Film Special (1:37:15): Depth in Text and Other Mediums (1:40:32): Patterns Across Nabeel's Taste: The Unfamiliar (1:43:11): Lightning Round: Travel (1:44:37): Stories Nabeel Tells Himself (1:45:31): Agency and Being Told What to Do by AI (1:47:49): Negotiation and Creating Optionality (1:50:28): Palantir's Vocabulary (1:53:07): Lessons from Tyler Cowen (1:54:41): Fighting Inertia Key Links (all references available here)"We don't get a lot of things to really care about." (Pig, 2021)The opposite of slop is care. (Tweet Thread)PrinciplesHow To Understand Things Video Games are the Future of Education Notes On Karl PopperReflections on Palantir 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

Che-Wei Wang and Taylor Levy are the founders of CW&T (Website, Instagram, X, TikTok), a Brooklyn-based studio creating products that exist somewhere between art, design, and engineering.The husband-and-wife team met at NYU ITP and shares a background across industrial design, architecture, computer science, film, including time at Pratt Institute and MIT. They won the 2022 Cooper Hewitt National Design Award for Product Design. They design and manufacture everyday objects including clocks, pens, tools, and other strange objects that challenge our relationship with time, attention, and materiality. Their most recognizable products include the Pen Type-A, Pen Type-C (my favorite), Time Since Launch (a one-time-use, 100-year timekeeper), and Solid State Watch, a remix of the classic Casio F-91W.Our conversation explores their fascination with time, their commitment to creating heirloom-quality objects in a disposable world, and how they've built a sustainable creative practice on their own terms. We discuss their prototyping-centered approach, the tension between digital and physical creation, and how they navigate collaboration as partners in life and work.Throughout, Che-Wei and Taylor reveal a philosophy that treats making as its own reward—they create what fascinates them first, trusting that others will connect with their vision. In a world increasingly dominated by disposable products and digital experiences, CW&T offers a refreshing counterpoint: a workshop where physical objects are thoughtfully conceived, meticulously crafted, and built to accompany us through life's journeys. Their work invites us to reconsider our relationship with the objects we use daily and the passage of time itself, offering a refreshing counterpoint to our increasingly digital, ephemeral world.Full transcript with all links and references.Timestamps(00:00): Time: a pattern across CW&T’s careers(11:21): Time Since Launch: the idea of counting up instead of down, and creating personal epochs (14:11): "Good design is long-lasting,” Durability of Electric Objects(19:31): Balancing art, product, and design: CW&T's approach to creating strange (but useful) things (23:51): First Word vs. Last Word Art: Michael Naimark's essay on innovation (28:01): Death by consensus: Why Che-Wei left architecture, and the joy of creative collaboration(32:52): Inspiration, Theory, and Self-Evidence(38:40): Tools: iPhone world, what makes a great tool, and design that optimizes for joy(44:21): The Hi-Tec-C pen cartridge and remixing what has come before(48:01): Making physical objects: a case for prototyping and against rendering(55:41): CW&T’s beloved products(53:27): ITP, Electrified Objects, Software in Objects(56:49): Dream Stem: Generative design, openness to new tools, AI's impact on the creative process, and intuition(01:07:11): The value of friction, and what's lost and gained in the pursuit of efficiency (01:09:46): CW&T the brand, contemplating CW&T's legacy and purpose(01:15:24): Kickstarter, owning your audience, and what it would look like to start today(01:19:35): Partners in life and work, the tension between merging identities and maintaining individuality (01:25:02): Growth, explore vs. exploit, and learning, dream collaborators, and more resources(1:33:56): Lighting round: great teachers, New York City focus & serendipity, creative inspirations, CW&T book, nature and green things, morphology and architecture, “form and force,” a gift for children or grandchildren, what to hang onto,(01:52:07): TimelessnessDialectic 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

Eugene Wei (Website, X) is a writer, product thinker, and cultural observer best known for his essays on technology, media, and social networks, including Status as a Service, Invisible asymptotes, and TikTok and the Sorting Hat.Eugene spent seven years at Amazon in its early days before following a brief detour to pursue filmmaking at UCLA. He then led product, design, editorial, and marketing teams at Hulu, co-founded Erly, and worked at Flipboard and Oculus. Today, he works on his own ideas at the intersection of media and technology while advising and angel investing.This conversation explores the evolving landscape of entertainment, social media, community, and humanity in our digital age—topics Eugene has examined deeply. We revisit some of Eugene’s greatest hits on how platforms like Twitter and TikTok shape society and also get into fresh ideas he's yet to share publicly.We start by discussing how today's social media world compares to the television-centric world that Neil Postman lamented in Amusing Ourselves to Death, and how entertainment-maximizing, adversarial, algorithmic social platforms might lead us to "Amusing Each Other to Death." Eugene unpacks TikTok's profound impact on our "digital nervous system," differentiating between social networks and social media—highlighting the latter's emphasis on frictionless positivity rather than meaningful connection.Amid rising nihilism among young people, Eugene analyzes how cultural and economic structures contribute to lost hope, exploring social media’s role in exacerbating these trends. We discuss power laws influencing tech, media, sports, and finance, and how that drives pervasive speculation across culture. Then, he traces these themes through American television, from 1960s-1990s sitcoms to shows like The Sopranos, Succession, and Industry, revealing how they reflect the erosion of community and purpose in late-stage capitalism.Throughout, Eugene offers nuanced observations on how technology's removal of friction has paradoxically weakened our sense of meaning and connection. We wrap up with how AI might shape media and creativity, what elements of humanity may be valued in the future, learnings from Bezos and film school, and a movie recommendation for anyone trying to make sense of it all.Timestamps(02:10): Amusing Each Other to Death and "Frictionless Positivity": Neil Postman, TV vs. Social Media(14:35): Dunking, Quote Tweets, and Proximity to the Other(19:09): Prisoner's Dilemma of Twitter: Concede or Dunk(24:52): Is TikTok the Final Form of Social Media?(31:02): Status Games in the Algorithm Era(39:02): Technology's Reduction of Friction & Avoiding Confrontation with the Other(48:45): The Internet's Reversal of Vita Activa and Vita Contempliva(50:53): Growing Nihilism Toward Online Status Games: If You Don't Capture Attention, You Aren't Relevant Anymore(55:54): Late State Capitalism's Disappointment, Gen Z Nihilism in US and China, Death of Community(1:03:01): Speculation Culture and Playing to the Power Law(1:08:08): NBA, NFL, Netflix, Power Laws, and Distraction-Friendly Viewing(1:15:55): Playing for Attention: the Only Goal(1:18:43): Video and Image vs. Text(1:20:57): The Subconscious of American Culture and the Decline of Community According(1:32:31): Terminally Online Culture, Role Models, Evolving Search for Meaning(1:45:23): Friction and the Internet's Impact on Communities(1:50:50): AI, "The Most Human Human" and Creativity(1:56:38): Lighting section: Invisible Asymptotes for Social Media and Eugene, and Writing(2:02:08): Beginner's Mindset, Film School, What Technologists Could Learn from Filmmakers(2:06:40): What Idea from a Book Would Be Most Compelling to "Transmute" into an Audiovisual Medium?(2:08:56): Bezos and Removing Friction(2:11:09): Left Brain vs. Right Brain, Engineering Problems vs. Human Problems(2:15:07): Why Film is Meaningful and a RecommendationEpisode transcript⁠ with all linked references: