Dialectic

Jackson Dahl

Conversational portraits of original people, across technology, media, business, and creativity. By Jackson Dahl.

  1. 37: Trevor McFedries - Creative People Should Be Rich

    1D AGO

    37: Trevor McFedries - Creative People Should Be Rich

    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.

    2h 19m
  2. 36: C. Thi Nguyen - Measurement, Meaning, and Play

    JAN 13

    36: C. Thi Nguyen - Measurement, Meaning, and Play

    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 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. Timestamps: 0:00: Opening Highlights1:39: Introduction to C. Thi Nguyen5:13: Thanks to Notion6:31: Start: What Does it Mean to Be Playful?13:41: Starting Local: Agency, Scoring Systems, and Games23:36: Value Capture: Incentives, Values, and the Collapse of Meaning36:28: What is the Shape of Good Values?49:45: Attention, Recognition vs. Perception, and Aesthetic Openness58:46: Process vs. Outcome, Striving Play vs. Achievement Play, Recipe vs. Dish1:10:00: Aesthetic Value & Autotelic Pursuits in Life1:16:59: Metrics, "Measure What Matters," and What We Miss1:24:16: Quantitative vs. Qualitative Ways of Knowing and Different Conceptions of Rules1:38:01: Scaling Trust, Data, Experts, and Legibility1:54:37: Objectivity & Truth, Value-Laden Technology & Decisions, and "Objectivity Laundering"2:07:57: Advice for Technologists: Ethics, Maps, Value-Neutrality, and Playfulness2:18:52: Closing Thanks to NotionDialectic with Jackson Dahl is available on all podcast platforms.⁠⁠⁠⁠⁠ ⁠⁠Follow ⁠Dialectic on Twitter⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠Follow Dialectic on Instagram⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠Subscribe to Dialectic on YouTube

    2h 22m
  3. 35: Brie Wolfson - Loving Attention & Ease in Craft

    JAN 6

    35: Brie Wolfson - Loving Attention & Ease in Craft

    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. Timestamps: 0:00: Opening3:54: Notion5:04: Intro: Craft, Finger Feel, and Staying Closer to the Ground Level13:27: Process vs. Output, Quality vs. Speed, and Great Editing21:44: Craft, Substance, and Truth in Marketing25:56: Individuals as the Building Block of a Company and Empowered ICs32:02: Creative Collaboration and In-Person and Remote36:46: Company Building: What is Changing and What Will Stay the Same44:25: The Soft Stuff: Great Company Values and Great Culture52:17: Thinking vs. Doing Cultures, 996 and Difficulty Sitting Still1:00:37: Morale, Fun, Amplifying Leaders, and Loving Attention1:11:58: Career Path Advice for Young People1:19:56: Kevin Kelly, Chasing Greatness, Illegibility, and Ease in One's Craft1:27:29: Special Talent and Contagious Ambition1:32:22: Brie’s Spike: Charisma, Hard and Soft, Making Things Fun, and Belief1:43:23: Taste, Appreciation, Generosity, Skill and Soul1:57:26: Great Editors, Saying No and Getting to Yes, and Being Receptive to Editing2:05:25: Great Writing: What do You Have the Right to Do that Others Don't?2:13:55: Grab Bag: Optimism and Pessimism, High and Low, and Closing Maxims2:30:07: Thanks to NotionDialectic with Jackson Dahl is available on all podcast platforms.⁠⁠⁠ ⁠Join the ⁠telegram channel for Dialectic⁠⁠⁠⁠⁠⁠ ⁠Follow ⁠Dialectic on Twitter⁠⁠⁠⁠⁠⁠ ⁠Follow Dialectic on Instagram⁠⁠⁠⁠⁠ ⁠Subscribe to Dialectic on YouTube

    2h 32m
  4. 34: Ryo Lu - It's All the Same Thing

    12/18/2025

    34: Ryo Lu - It's All the Same Thing

    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 Future4:45: Intro7:46: "It's all the same thing!"17:25: Technical and Conceptual Readiness and How AI Helps us Deal with Complexity20:58: Designing for true-ness and inevitability27:28: Practicality and False-Compromise33:45: Working with Material and Different Ways of Thinking44:06: ryOS and Designing for the Full Spectrum of Users59:39: Allowing for Slack and Some Amount of Chaos in Design1:04:55: What is Cursor, Conceptually?1:10:33: How Using Cursor Evolves1:15:50: Designing for Power While Not Alienating Users1:19:59: How Ryo Designs at Cursor: Abstractions, Writing, Prototyping1:23:57: Process, Creating Soulful Things with AI, Refining Taste1:31:08: Balancing Agility and Quality, Chaos and Order1:37:00: Great Teams and Great Products1:39:41: Grab Bag: Human Tech, Why Tools Need Stories, Why Cursor Isn’t a Slot Machine, Notion & Cursor, Steve Jobs, Liquid Glass1:56:16: Tenderness & EmpathyDialectic with Jackson Dahl is available on all podcast platforms.⁠⁠⁠ ⁠Join the ⁠telegram channel for Dialectic⁠⁠⁠⁠⁠⁠ ⁠Follow ⁠Dialectic on Twitter⁠⁠⁠⁠⁠⁠ ⁠Follow Dialectic on Instagram⁠⁠⁠⁠⁠ ⁠Subscribe to Dialectic on YouTube

    1h 60m
  5. 33. TBPN (John Coogan & Jordi Hays) - Inside Tech's Water Cooler

    11/17/2025

    33. TBPN (John Coogan & Jordi Hays) - Inside Tech's Water Cooler

    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 Highlights03:18: Intro & Background06:08: Technology vs. Business and the Strategy behind TBPN12:08: Building a Media Business when Distribution is not Scarce22:26: Being Entrepreneurs and Talent30:33: Avoiding Audience Capture35:57: Why Advertising is a Good Model44:04: Technology's Circular References and Borrowing Ideas from New Places53:20: Narrow vs. Wide Appeal59:44: X (Twitter)-First Content and Other Platforms1:14:35: Making Content People Want to Share and Taking Yourself Seriously and Unseriously1:20:28: Valuing Brand1:30:10: Balancing Focus and Iteration1:35:25: Endurance & Evolution1:40:34: A Day in the Life of TBPN & Learning to be Newscasters1:49:59: Jordi & John as a duo, Will Manidis, and the beginnings of TBPN2:02:57: 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 Follow ⁠Dialectic on Twitter⁠⁠⁠ Follow Dialectic on Instagram⁠⁠ Subscribe to Dialectic on YouTube

    2h 22m
  6. 32: Chris Sacca - Drifting Back to Real

    11/05/2025

    32: Chris Sacca - Drifting Back to Real

    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

    2h 36m
  7. 31: Gabe Whaley - Playing the Crowd & Outlasting the Hype

    10/15/2025

    31: Gabe Whaley - Playing the Crowd & Outlasting the Hype

    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, and Focus(1:14:09): Creating as a Collective and Gabe's Role in Enabling the Team(1:22:30): Trust, Shedding the Black Box, and Staying Original(1:30:35): Applied MSCHF – Doors are Open(1:34:21): Sarah Andelman, People Who are Still Excited, and Long Time Horizons(1:41:52): Buzzfeed(1:44:41): MSCHF ValuesLinks Made by MSCHFSean Monahan11. Eugene Wei - Amusing Each Other to Death - DialecticBig Red BootMSCHF WholesaleTax Heaven 3000Chair SimulatorMaurizio CattelanBirds Aren't RealDavid Bowie interviewBlurJesus ShoesAthletic Aesthetics - Brad TroemelLil MiquelaTrevor McFedriesHow Twitter Gamifies Communication - C Thi. NguyenDisney diagramEva & Franco MattesComedian - Maurizio Cattelan#13: Gabe Whaley - Making MSCHF - Scott NortonSarah Andelman ColetteEmmanuel PerrotinKAWSATM LeaderboardOpus 40Key4AllPT Cruiser from Key4AllSatan ShoesSuper BabyMSCHF on Instagram Dialectic is on all podcast platforms. Join the ⁠telegram channel for Dialectic⁠ Follow ⁠Dialectic on Twitter⁠ Follow Dialectic on Instagram Subscribe to Dialectic on YouTube

    2h 4m
  8. 30: David Senra - The Clarity of Commitment

    09/30/2025

    30: David Senra - The Clarity of Commitment

    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 Twitter⁠Follow Dialectic on InstagramSubscribe to Dialectic on YouTube

    2h 17m

Ratings & Reviews

5
out of 5
27 Ratings

About

Conversational portraits of original people, across technology, media, business, and creativity. By Jackson Dahl.

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