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Dialectic

Jackson Dahl
Dialectic
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  • 29: Billy Oppenheimer - Attuned to Clues
    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
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  • 28: Maxwell Meyer - Starships & Road Trips
    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
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  • 27: Mackenzie Burnett - Accounting for the American Dream
    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
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  • 26: Cyan Banister - A Fool’s Dérive
    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
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  • 25: Reggie James - Our Infinite Mirrors (Live at FWB Fest)
    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
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Conversational portraits of original people, across technology, media, business, and creativity. By Jackson Dahl.
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