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Dialectic

Jackson Dahl
Dialectic
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  • 27: Mackenzie Burnett - Accounting for America
    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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  • 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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Conversational portraits of original people, across technology, media, business, and creativity. By Jackson Dahl.
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