Dialectic

Transcript and all links: dialectic.fm/mmm Molly Mielke McCarthy (Website, X, Substack) is an investor, writer, and founder of Moth Fund, an early-stage fund focused on backing "moths": quirky, quiet, mission-driven founders who are often underpriced by traditional venture capital. Molly's career has been a dance between "peopling" and making. She's held design, product, and editorial roles at Figma, Notion, Stripe Press, and The Browser Company, and explored film, photography, and the arts before finding her way to venture, where she started as a scout for Sequoia Capital. Today, she invests in people at the earliest stages. She also writes beautifully about agency, vocation, discernment, and what it means to live an authentic life. We begin with how Molly identifies exceptional people—her "three-month rule," spikiness, and why competence is harder to find than storytelling. We discuss the bat signal she sends to attract founders who feel misunderstood, and one of her central distinctions: agency versus ambition, or why playing your own game matters more than playing games others have created. We go deep on commerciality and why it is so essential, and talk about how Molly's work as an investor often looks most like coaching. We also explore legibility versus illegibility: the freedom in not being easily understood, and when it's worth becoming legible. Molly's one of my favorite thinkers on self-knowing, and we talk about how she's navigated uncertainty toward authentically shaping her life and work into a form that fits her. Molly embodies rare combinations: people-centric yet fiercely individual, intuitive yet pragmatic, truth-seeking yet full of care. I hope this conversation inspires you to yield to your own calling, and to be patient enough to see what's true about yourself and the people around you. --- Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts. My “What are You Building This Year feature with Notion on Instagram. Timestamps 0:00: Opening Highlights 1:29: Intro to Molly 3:36: Thanks to Notion 5:14: Start: People, Spikeyness, and Discernment 21:36: Agency and Ambition 34:45: Commerciality 49:19: Investing, Feedback Loops, and Creating a Bat Signal 59:46: Coaching and Working with Young People 1:06:54: Self-Knowledge, Uncertainty, "Should," Others' Acceptance, Motivations 1:16:38: Illegibility & Legibility, Principles, Authentic Service 1:29:28: Friends, Seeing in the Third Person, Feminity in a Masculine World, Love 1:42:07: Grab Bag: Art, Catholicism, Gratitude, Beauty 1:58:58: Thanks Again to Notion

All linked references & transcript available at dialectic.fm/trevor-mcfedries. Trevor McFedries (X, Instagram, Wikipedia) is a musician, technologist, and entrepreneur. Today he is the founder of Runner and 1/2 of electronic dance duo SoFTT. Previously, Trevor was co-founder and CEO of Brud, the company behind Lil Miquela that was acquired by Dapper Labs; Founder of FWB (Friends with Benefits); early artist in residence at Spotify; and a touring DJ who performed as DJ Skeet Skeet, was part of the rap group Shwayze, and produced for a range of artists. Trevor’s work emerges from a tension he’s lived with throughout his career: the gap between who creates cultural value and who captures it. Growing up poor in Iowa and entering the dying music industry in the late 2000s, he witnessed firsthand how the instruments that capture value rarely benefit the creative people who generate that value. This has run across his entrepreneurial work, from building virtual pop stars to a range of crypto projects that hope to give creative people more upside. Trevor bridges culture and technology, art and capital, and high and low. I’ve met few people who are as consistently ahead of culture. His perspective challenges both the art world’s disdain for commerce and Silicon Valley’s shallow engagement with culture, arguing instead for creative people to play the game on the field and build the instruments that will make them rich. Today, he’s focused on how that may end up being as much about predicting what’s next with stakes as it is actually making things. We also talk about authenticity and honesty, why he continues to spend time in crypto despite it being low status, why speculation is rational and selling out is punk, how power comes from consensus, his keen nose for weird—especially on the internet, briefly working with Kanye West, and his forever optimistic curiosity. --- Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts. You can read more about why Notion embodies Dialectic’s values and our partnership announcement here. My “What are You Building This Year feature with Notion on Instagram.

Full episode transcript and all linked references available at https://dialectic.fm/c-thi-nguyen. C. Thi Nguyen (Website, Philpeople.org, X) is a professor of philosophy at the University of Utah focused on values, games, agency, art, aesthetics, and data. His new book, The Score: How to Stop Playing Somebody Else's Game is out now. Thi is also the author of Games: Agency as Art, in which he explores how game designers work in the medium of agency, but sculpting a players abilities, goals, and obstacles to create "harmonious action." I first learned about Thi's work via his interview with Ezra Klein in 2022, which is one of my all-time favorite podcast episodes. In it, he discusses Agency as Art, How Twitter Gamifies Communication, Why Q-Anon is game-like, and more. The Score is a marriage of his work on games and on data and metrics. He explores how scoring systems in games allow for playfulness and agentic exploration of our values, while scoring systems in real life produce what he calls value capture. In an effort to make the world more quantified, comprehensible, and trustless, metrics are flattening our values and sapping the meaning out of our lives. One way he describes his work is that James C. Scott's Seeing Like a State also applies to the human soul. In this conversation, I aimed to cover the most compelling ideas in the book in two parts. First, we explore the local side: personal agency and values, attention and the difference between recognition and perception, process vs. outcome, and why playfulness and openness allow us to have richer lives. He also shares how games are a compelling template for this kind of exploration. Second, we talk about the societal level: what we miss in a world of values dominated by what is easily measurable, how we can scale trust and enjoy the benefits of collaboration, science, and technology while not delegating our understanding to the wrong people, and why objectivity and truth are not always the same thing. Thi makes the case that technology is value-laden, not value-neutral, and that we must be more vigilant and nuanced in our approach to the ethical decisions that exist everywhere. I hope this conversation is a prompt for you and I to think more deeply about what we truly care about, to "move lightly" between agentic and value-laden worlds, and bring a perceptive playfulness to our lives. Remember, we are all grasshoppers in disguise. If you enjoy the episode, please support Thi's work and check out The Score. - Dialectic is presented by <...

Full transcript and all links: ⁠https://dialectic.fm/brie-wolfson⁠ Brie Wolfson (X) is a marketer, writer, storyteller, and curator. She’s Chief Marketing Officer of Positive Sum & Colossus, where she works closely with CEO Patrick O’Shaughnessy across investing and media and spearheaded Colossus Review, their new print publication known for superb long form profiles. Brie also recently joined AI-programming behemoth Cursor as Head of Employee Experience and wrote about the company’s culture. She has worked with craft-oriented software companies throughout her career, including Stripe—where she helped launch Stripe Press and the company’s planning function, among other things—and Figma, where she worked on Education. In her words, she is drawn to companies where the reality is even more impressive than the reputation, and she has publicly and privately worked with a number of the most impressive leaders in Silicon Valley on marketing, culture, and storytelling. We cover a broad range of Brie’s expertise, including craft, marketing, organizational culture, unlikely career paths, and taste, editing, and writing. This includes how AI is causing companies to become even more oriented around the empowered individual contributor and who the best of them, including company leaders, are focused on an attunement to details that she likens to “finger feel.” We also talk about why she believes marketing should be a kind of truth-telling, closing the gap between reality and perception. She also reflects on the common cultural thread of great companies: a deep-seated desire to be a great company, not just create great products. She talks at length about everything she’s learned from amplifying special people and how she’s navigated the tension in her own desires for fun and breadth and ambition toward greatness. I hope this conversation inspires you to raise your standards, get to the ground level, and settle into a life of deep attention that produces quality, usefulness, and joy. --- Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts. You can read more about why Notion embodies Dialectic’s values and our partnership announcement here. You can find the essay from Notion CEO Ivan Zhao mentioned at the end of the episode here. Ti...

All links and transcript at dialectic.fm/ryo-lu Ryo Lu (Website, X) is the head of Design at Cursor. Prior, he was a designer at Notion, Stripe, and Asana, working on some of the most influential software tools of the last decade. He is now focused on building the next generation of tools for making software. Our conversation is an extensive exploration of Ryo's design philosophy, which is anchored in his recurring mantra: "it's all the same thing." He sees the world as fundamentally modular, where simple rules and patterns endlessly recombine to create emergent complexity. For Ryo, design is consciously participating in this process: seeing through the surface to understand the underlying structure and rearranging it into new forms. This means constantly moving between simplicity and complexity, chaos and order, bare material and highest levels of abstraction. We discuss how his process has evolved with AI. In the past, designing in tools like Figma felt like painting; now, working in Cursor feels like sculpting clay or finding David in the marble. So much of his philosophy is about getting closer to the material—in this case, code—and letting it provide feedback. There is no better example of this than his personal project, ryOS, a nearly full-on operating system he built entirely in Cursor. It is soulful, deeply personalized, and the opposite of "AI slop." This is a philosophical discussion about designing things that feel "true" or even "inevitable," but it is also a practical one. We talk about balancing agility and quality, allowing for "slack" in systems, and how to create soulful things with AI. Ryo is a profound thinker, but he is also a prolific doer, and it is this marriage that makes him so effective. I hope you are inspired to get closer to your own material, to be more flexible and dynamic, and to expand the boundaries of what you can personally create. --- Dialectic is now presented by Notion. I am now focused on Dialectic full-time, thanks to their support. You can read more about why Notion embodies Dialectic's values and our partnership announcement here. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts. Timestamps 0:00: Notion Announcement & Dialectic's Future 4:45: Intro 7:46: "It's all the same thing!" 17:25: Technical and Conceptual Readiness and How AI Helps us Deal with Complexity 20:58: Designing for true-ness and inevitability 27:28: Practicality and False-Compromise 33:45: Working with Material and Different Ways of Thinking 44:06: ryOS and Designing for the Full Spectrum of Users 59:39: Allowing for Slack and Some Amount of Chaos in Design 1:04:55: What is Cursor, Conceptually? 1:10:33: How Using Cursor Evolves 1:15:50: Designing for Power While Not Alienating Users 1:19:59: How Ryo Designs at Cursor: Abstractions, Writing, Prototyping 1:23:57: Process, Creating Soulful Things with AI, Refining Taste 1:31:08: Balancing Agil...

John Coogan & Jordi Hays are the hosts of TBPN (X, YouTube, Spotify, Substack), a daily live show covering the technology business. TBPN was launched only about a year ago, but has become a mainstay in tech culture and a center of gravity forterminally online technologists. John was previously an EIR at Founders Fund and tech YouTuber. He co-founded Lucy Nicotine and Soylent. Jordi has co-founded and invested in many business including Party Round/Capital and Branded Native, a podcast and youtube ad network. We cover the origins of TBPN, or the Technology Business Programming Network, from its beginnings as "Technology Brothers" to the interplay between John's love for technology and Jordi's for business. They share how they've built a media business in an era of infinite competition by leaning into high volume and constant iteration, all while treating media as the "main thing." We discuss brand building and innovating on form by borrowing ideas from outside the tech industry—from Formula One and SportsCenter to Hollywood films—to avoid tech's tendency toward circular references. We also talk about their focus on X/Twitter and a niche, highly informed audience, rather than trying to go too wide. We also chat about what makes their partnership work and how they take the work incredibly seriously while not taking themselves seriously at all. Transcript and all links available at https://dialectic.fm/tbpn Timestamps 00:00: Opening Highlights 03:18: Intro & Background 06:08: Technology vs. Business and the Strategy behind TBPN 12:08: Building a Media Business when Distribution is not Scarce 22:26: Being Entrepreneurs and Talent 30:33: Avoiding Audience Capture 35:57: Why Advertising is a Good Model 44:04: Technology's Circular References and Borrowing Ideas from New Places 53:20: Narrow vs. Wide Appeal 59:44: X (Twitter)-First Content and Other Platforms 1:14:35: Making Content People Want to Share and Taking Yourself Seriously and Unseriously 1:20:28: Valuing Brand 1:30:10: Balancing Focus and Iteration 1:35:25: Endurance & Evolution 1:40:34: A Day in the Life of TBPN & Learning to be Newscasters 1:49:59: Jordi & John as a duo, Will Manidis, and the beginnings of TBPN 2:02:57: Grab Bag: Bias to Action, 15 Minute Interviews, Not Journalism, Talent, and Domination of Spirit Dialectic with Jackson Dahl is available on all podcast platforms.⁠ Join the ⁠telegram channel for Dialectic⁠⁠<...

Chris Sacca is an investor and founder of Lowercarbon Capital and Lowercase Capital. Prior to becoming an investor, Chris grew up in Buffalo, NY; studied around the world by way of the Georgetown School of Foreign Service; turned his student loans in $12M in the tech bubble of 2000 before losing it all and then some; and broke into Silicon Valley before eventually landing at Google, where he won the founders award. Then Chris started angel investing, which led to his first venture fund, Lowercase I. Lowercase I is one of if not the best performing VC funds ever, by multiple, at 214x, and included Twitter, Uber, Instagram, and more. Toward the end of Lowercase, I had the pleasure of working with Chris. Around that time, he was also a Guest Shark on Shark Tank. Chris was heavily involved in both Obama campaigns and was a large supporter of Hillary Clinton in 2016. When Trump won, he wound down new investing at Lowercase and "hung up his spurs" to focus on political and democracy related efforts. Then, in 2018, Chris started Lowercarbon Capital to invest in "un-f*cking the planet": carbon removal, climate science, cooling the planet, and eventually nuclear fusion. We talked about writing and storytelling, keeping people around who keep you honest, having a good taste in "weird," playing rigged games, taking the right kind of risks, and how even billionaires have imposter syndrome. We also get into how great founders embody inevitability, what makes the people at Lowercarbon special, how much Chris thinks about AI, and the many chapters of Chris's life, including whatever might be next. Authenticity is a moving target for all of us, but one of the things I most admire about Chris is his ability and desire to shamelessly play his own game.Timestamps: (0:00): Open: The Common Thread Amongst The Best Founders (1:20): Intro (3:42): Coast to Coast (12:29): Leaning into Weird & Investing in Fusion (24:35): Having People Who Keep You in Check (32:00): The Power of Language and Stories (1:03:03): Investing, Risk, and Wild Confidence (1:27:57): Imposter Syndrome and Making Companies Better (1:38:03): Lowercarbon's Team and Culture (1:57:47): Chris's Life Chapters, AI, and Creative Outlets (2:22:04): Drifting Back Towards Real All links and transcript available at https://dialectic.fm/chris-sacca 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

Gabe Whaley is co-founder and CEO of MSCHF (Instagram, Wikipedia), the art collective, fashion and footwear brand, startup, and fill-in-the-blank, famous for its viral products and cultural interventions. A few notable works include Jesus Shoes (Nike Air Max filled with holy water), Severed Spots (a "decentralized" Damien Hirst print), Museum of Forgeries (One original Warhol and 999 perfect forgeries), and of course the Big Red Boot. This conversation was heavily influenced by MSCHF's recently released Made by MSCHF, a "textbook," through which the team peels back the curtain and shows us inside the black box that has produced more viral hits than one can count. Gabe had a sheltered childhood and went to two years of army academy at West Point before eventually finding his way to New York City to intern at Buzzfeed around 2014. In his spare time, he started releasing weird internet projects under the name "Miscellaneous Mischief." After tasting virality a few times, he started collaborating with likeminded creatives and eventually formalized MSCHF in 2019. I've known Gabe for many years (and even did a small collaboration with him from my seat at 100 Thieves). We sat down to reflect on the last 15 years and the arc of MSCHF, what made it special, and where one goes next when virality makes you feel nothing and the internet feels mature. The conversation includes MSCHF's eye-of-the-beholder legibility, their obsession with value, the power of mystery, and how the product doesn't culminate with release, but after the audience has made it their own (in MSCHF parlance, "playing the crowd"). We also discuss the creative process behind the hit factory, how acting as a label rather than individuals changes their relationship to the work, whether the cultural future is actually canceled, how the internet has changed, and how real world experiences offer something to the creator and the consumer that digital life simply can't. We wrap-up by speed-running through many of MSCHF's internal values, from "always punch up," to "death is just as importance as birth," to perhaps its defining frame: "nothing is sacred." I hope you are inspired toward play, originality, embracing discomfort, and having the courage to burn it all down and start anew. Full transcript and all linked references: https://dialectic.fm/gabe-whaley Timestamps (0:00): Intro (2:21): Value and Legibility (13:24): Is the Future Canceled? (20:00): We Create as a Result of What We Believe In (26:11): What Makes a Good Remix (29:08): How MSCHF Relates to the Current Thing and Evolves What Game it Plays (38:31): Creating Something the Crowd Can Play (44:59): Emphasis on Craft and Objects Rather than Creating "Lifestyle" (47:27): Keeping Up in a World That Demands Constant Production (53:11): Resisting The Internet's Scale and Lack of Friction (1:03:15): Accidental World Building, Process, Creative Inputs,...

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-senra Special 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 Him Dialectic with Jackson Dahl is available on all podcast platforms.Join the ⁠telegram channel for Dialectic⁠Follow ⁠Dialectic on Twitter⁠

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-oppenheimer Timestamps: 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 Door 1:15:55 - 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 Varty Eddie Murphy Is Tracy Morgan's Favorite | Comedians In Cars Getting Coff...

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/subscribe Full transcript and all links: https://dialectic.fm/maxwell-meyer Timestamps: 00:00: Intro 01:14: Elon, The Media, Cliché, American Collectivism, and Cultural Pendulum Swings 09:07: Media, Criticism, and Defending the New 17:49: American Ideology: The Declaration, Communal Enterprise, Americans as Movers 28:20: Patriotism 33:36: Learning from the Rest of the World 40:27: A Case for Progress 49:38: Tech's Separation from American Culture in the 2010s 58:44: Tech Accountability and Engaging Normal People on their Premises 1:15:23: 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 Government 1:28:46: Principled and Unpredictable Thinkers 1:34:06: The Case for Capitalism 1:43:07: Defending Critiques of Capitalism and Concerns of Concentration of Power 1:49:37: Arena, Good Writing and Editing, Magazines as a Medium, Durability, Influences 2:02:19: Big and Small America 2:06:16: Joe Lonsdale 2:06:50: Upholding Abundance 2:11:39: Cooking and Bringing People Together 2:12:38: The Back Half of the Brain 2:14:02: The Places Between Places Key Links: The Man-Made Miracle of SpaceX - Max Meyer Max Meyer Launched a Print Magazine in 2024. Here’s Why. - Infinite Loops Podcast Man i...

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 --- Timestamps 00:01:11 Intro 00:02:51: The American Heartland 00:05:21: Agriculture, Policy, and Government 00:12:29: The Challenges with Prioritizing Climate Risk: "Long Term and Abstract" 00:18:04: Pragmatic Environmentalism and Resilience that Drives Business 00:21:49: The American Dream 00:25:52: The Importance of Independent Small Businesses 00:28:58: Entrepreneurship on the Frontier: America's First Entrepreneurs and Ambrook's First Customers -- Farmers 00:36:28: Biological Factories: Why Farms are Complex Businesses 00:40:41: Why Everything Goes Back to Accounting 00:44:30: Why Money Movement Matters 00:51:13: Ambrook as a Twenty-Year Container 00:57:27: The National Importance of Agriculture 01:00:49: The Features of Illegibility 01:04:49: Ambrook's Long Term Vision 01:10:17: Making the Intractable Tractable (And Doomscrolling Your Company's Slack) 01:14:42: De-Risking and Becoming Friends with Anxiety 01:17:26: Building Something That Takes on a Life of its Own 01:20:07: Ambrook's Culture in Three Words 01:21:26: Brand and Storytelling 01:26:11: AI Enabling the Middle Class 01:30:57: California History and J.G. Boswell 01:34:05: Niche Subjects and History and "The Land Where Lemons Grow" 01:36:46: Disney's Magic Band 01:39:15: Strange Math and Happiness and Sadness in Parallel 01:41:31: Aesthetics, Beauty, and Physical Design Systems 01:47:31: The Draw to Start Things Links & References America, the Beautiful - Mackenzie Burnett

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-banister Timestamps 0:01:23: Intro 0:03:45: Cyan's "Church" 0:16:21: Stillness, Mindfulness, and Introspection 0:28:47: Learning to See in Original Ways 0:39:38: People: When the "Light is On," "Collecting Minds," and Conjuring Friends 0:46:55: Cultivating Childlike Joy and Refusing to be a Victim 0:52:30: Radical Accountability 0:56:28: Randomness, Faith, and Experimentation 1:06:22: Conviction and Peter Thiel 1:12:54: Returning to Seed Investing and Long Journey Ventures 1:18:23: Thoughts on Art 1:23:42: Performance Art 1:26:37: Cyan's Creative Projects 1:32:51: Boredom 1:36:06: Living Around Elderly People 1:42:14: Pete Buttigieg 1:45:57: Being a Role Model 1:48:26: Young People's Future 1:52:46: Scott Banister and Lessons for Her Kids 1:55:35: "It Just Doesn't Matter" And Who Pulls the Strings Key Links Cyan - by Kevin Gee and Dan Scott - Cloud Valley Cyan Banister — From Homeless and Broke to Top Angel Investor - Tim Ferriss

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-james Video version from FWB livestream available here. Timestamps 3:05: Technology as Mirror 8:04: De-fanging Loaded Technologies 12:43: Writing's Role in the Design Process 16:13: Affordances, Software, Hardware, and Values 22:53: Universal Luxuries 25:46: Friction and How Technology Can Make us Feel 30:16: The Role Brand Plays in Technology Today 34:30: Successful Narratives in Crypto 41:30: Crypto as a Mirror 44:39: American Myth & West 47:56: Personal Myth 54:16: Vision References What Technology Wants - Kevin Kelly Crying in the Garden ~ Closing Eternal - Reggie James Joan Didion on writing to think Universals & Luxuries - Reggie James Naoto Fukasawa: Embodiment - Naoto Fukasawa THE TOKYO TOILET ‎Perfect Days (2023)

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-lee⁠⁠ Timestamps: (2:23): Values and Technology as an Amplifier for Agency (9:57): Instrumental vs. Engaged Interfaces and Tools (20:05): Representations, Abstraction, and Exposing Complexity (33:23): Dreaming of Thinking Tools, Especially Beyond Text (48:06): LLMs, Mechanical Thinking, and Going Beyond in How We Understand (57:42): Embeddings of People (1:01:16): Applying Rigor and an Engineering Approach to Working with LLMs (1:08:26): Collaborating with AI: Having Agents Work for You vs. Accelerating Your Craft (1:11:10): Using LLMs to Explore Latent Space (1:14:58): Working at Thrive: building internal tools and taking software seriously at a VC firm (1:28:09): What Great Engineering in an Organization Looks Like (1:33:50): Humanity, Aliveness, and Technology (1:39:41): Dreams, Aesthetics, Imagery, and Intentionally Guiding Technology (1:46:09): Lost to Wonder References ⁠⁠What are conference talks about? - Linus⁠⁠ ⁠⁠Instrumental interfaces, engaged interfaces - Linus⁠⁠ ⁠⁠What makes a good human interface? - Linus⁠⁠ ⁠⁠Dialectic Ep. 21: Geoffrey Litt - Software You Can Shape⁠⁠ ⁠⁠Linus Lee on Representations for MIT Media Lab Lecture⁠⁠ ⁠⁠On Exactitude in Science - Jorge Luis Borges⁠⁠

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-winter Timestamps 2:09: Taste, absorbtion, and influences 10:54: Deploying your taste 15:49: Ideas that matter and taking yourself seriously 22:13: Aesthetics 24:16: Choosing Teachers and Authors 28:15: Charisma & delightfullness privilege 34:59: Living a relational life 44:07: Trust, social scaffolding, and small talk 51:01: Erosion of social norms, low-trust environments, and load-bearing infrastructure 1:02:17: Cultural arson and the dark sides of "you can just do things" 1:15:44: The healthy kind of agency 1:20:45: Tammy's N-of-1 path and who she aspires to rhyme with 1:28:38: Red herrings of success and focusing on outcomes 1:32:22: Assortive everything 1:37:52: Personal and professional standards 1:43:06: Journaling, great writing, and audience 1:57:29: Reading & Biographies Key Links: The Art of Doing Science and Engineering - Richard Hamming On Self-Respect - Joan Didion Scaling People - Claire Hughes Johnson High Growth Handbook - Elad Gil Virginia Woolf on Montaigne Ava on Tammy Old Enough!

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-asparouhova Timestamps: 1:31: Why Ideas Matter 9:33: The Last 10 Years of the Internet and Attention Collapse 17:07: How The Internet Caused Attention Collapse 19:59: Private Coordination in Public Spaces 24:01: Legibility and Illegibility as a Tactic 28:28: Ideas Are Not Created Nor Discovered; They Infect Us 35:17: Defining Antimemes 42:00: Ideological Black Holes: Supermemes 49:13: Engaging in the Public Square vs. Opting Out 54:16: Truth Tellers who Can Bring Anti-Memetic Ideas to Light 1:05:06: Champions, or the Great Apostle Theory 1:10:57: Institutions, Ideologies, and Movements 1:24:51: Attention 1:31:30: Jhanas 1:38:42: Writing a Book 1:46:19: Connecting the Dots in Reverse 1:50:29: Lightning Round: Fighting (or Working With) Human Nature, Software as Passion Project, Democracy, Space Away from the Center of Things 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

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. --- Timestamps 2:12: Agency in a Digital World and Geoffrey's Creative Medium: Software ...

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. --- Timestamps 1:41: 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 Life Key Links & References (all available at dialectic.fm) YOUTH MODE - K-HOLE

Full transcript and all links: dialectic.fm/henrik-karlsson Henrik 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. --- Timestamps 2:36: Self-Cultivation, Introspection, and Larry Gagosian 8:46: Writing to Think 16:05: 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 Future 25:12: Self-Criticism and Kindness to Your Past Self and Ideas 28:44: 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 Freedom 38:09: "Fit," Unfolding, Making Contact with Reality, and Designing Your Life with Experiments 49:06: Seeing Past Blindspots and Listening to Feedback the World Gives Us 1:04:16: The Ro...