Dialectic

Episode

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  54: Ian Rogers: Never a Spectator 10.08.2026 2j 37mnt

  Full transcript and all links and references: ⁠dialectic.fm/ian-rogers⁠. Ian and I made a playlist with albums/songs mentioned here (Apple, Spotify). Ian Rogers (X, LinkedIn) is Chief Human Agency Officer of Ledger, the Paris-based security company whose hardware wallets secure much of the world's crypto. He now focuses on how Ledger can enable us to work with AI agents while maintaining our secrets and value. His career has spanned music, culture, brand, and "the technolog(ies) people are going to hate next." He built and ran the Beastie Boys web presence in the 90s before working on music on the internet for over a decade: file sharing Nullsoft (Gnutella and WinAmp), early streaming at Yahoo!, direct-to-fan commerce at Topspin, Beats Music, and finally Apple, as an abbreviated list. He then joined LVMH as its first Chief Digital Officer, working with Bernard Arnault and its many Maisons to bring them into the internet era. More recently, he joined Ledger to improve its product experience, including collaborating with Tony Fadell to create Ledger's flagship form factor, Ledger Stax. Ian's roots are skateboarding and music, which formed alongside a punk rock ideology while growing up in Indiana in the 1980s. I am glad to have captured a long conversation that covers the many flavors of Ian, and the threads that have persisted through his many lives. That includes: individuality; being a participant, not a spectator; what makes a scene; building brands; trying to help Kanye; and why new culture is always being made—it's just that you have to find the 1% that's awesome. Also: ushering forward and translating frontier technologies; being pushed by Jimmy Iovine; why security matters in the AI era; why AIs aren't people; what he wants to automate; learning to fail; advice on relationships across work, parenting, and love; and a whole lot of love for music—from his 2026 pick Twisted Teens to his desert island albums to tea with Paul McCartney. I hope you're inspired to participate in the world and make great things. Thanks to our friends at Ledger for hosting me. --- Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. You can learn more at notion.com/dialectic. --- Timestamps (0:00) Opening Highlights (1:37) Intro to Ian & Thanks to Notion (5:22) Start: Tattoos, Individuality, and Punk Rock: Spectator vs Participant (16:44) What Makes a Scene? (25:24) New Culture, 99% of Everything is Garbage, Finding the 1% (40:09) Niche, Quality, and The Blockbuster vs. The Snowball (53:35) Brand, Selling Culture Before Product, and The Age of the Individual (1:08:12) Aggression, Patience, and Being Pushed (1:16:52) Translating New Technologies, Empowerment, and Agency (1:25:19) Interfaces, Ledger, Security, and Ideology (1:39:56) Ian's New Role: Chief Human Agency Officer (2:06:03) Seeing What is Real, Comfort Being Wrong, Chasing What's Fun and Cool (2:13:45) Lessons from Skateboarding and Favorite Albums (2:22:56) Working with Your Friends, Parenting, Love, and Remembering to Stay a Participant (2:35:47) Thanks Again to Notion
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  53: Zhengdong Wang - Feeling the Wave 29.07.2026 2j 7mnt

  Zhengdong Wang (Website, X, LinkedIn) is an AI researcher based in London. He writes annual letters (inspired by Dan Wang), mainly about AI progress, and his 2025 letter blew me away and inspired me to meet him. In it, he describes his ‘compute theory of everything,’ and makes the case that it would be stranger if AI progress slowed down than if it continued. Put a different way, reading his letter helped me get closer to truly feeling the wave of AI progress. It took Zhengdong a long time to become “AGI-pilled,” despite years of feeling like he was late to AI and working as a research engineer for the last five. I talked to him about what it will take for the rest of us to see what he sees, and feel what he feels. We also discuss why AGI may be a hazier target than simply seeing AI progress as “the model does the eval,” and why recursive self-improvement may be both happening and less fantastical than it may seem. ZD makes the case that based on the rate of progress and scaling, skeptics will simply be proven right or wrong soon. We talk a bit through what narrative and political challenges the AI industry faces ahead of this transition. Then there are the implications of all of this—namely how AI progress accelerates the question of what we each value, how we will spend our time, and where we will find or create meaning. ZD takes a stab at some of those impossible questions and shares some other favorite miscellanea that is reflective of the range of his letters. I hope this conversation helps you feel the wave a bit yourself, and that you remember that, regardless of how much change lies ahead, we still get to make our meaning. We get to choose. Full transcript and all links: dialectic.fm/zhengdong --- Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. You can learn more at notion.com/dialectic. --- Timestamps: (0:00) Opening Highlights (1:16) Intro to Zhengdong & Thanks to Notion (4:33) Start: Why Research: "I Just Want to Know" (12:25) The Model Does the Eval: AGI as a Moving Target, RSI, and Laser Beams (33:17) The Compute Theory of Everything and Feeling the Wave (53:17) The Myths AI Needs, Competition vs. Power Concentration, and Whether Progress Is Inevitable (1:13:42) "Who Could Possibly Compete?": Post-AGI Meaning, Work, and Questing (1:29:28) Are You Having Fun? Vacations, Mattering, and How to Live (1:47:13) Annual Letters, Economist Obituaries, London, and Burke (2:06:33) Closing & Thanks to Notion
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  52: Jack Conte - Draw the Next Page 21.07.2026 1j 51mnt

  Full transcript and all links: ⁠dialectic.fm/jack-conte⁠ Jack Conte (Patreon, YouTube, YouTube Pt2, X, LinkedIn) is the co-founder and CEO of Patreon. He is also a lifelong artist and musician, who at his peak released 100 music videos per year between his bands Pomplamoose (a duo with wife Nataly Dawn) and Scary Pockets (a funk collective), and was a longtime YouTuber. Jack is not a tech CEO who happens to like music. He is an obsessive, prolific artist whose first conventional job is running Patreon. This has shaped him as a founder and executive, and his mission at Patreon is to build an enduring and truly creator-first company that empowers creators to earn a living from their work. We began with how he manages to do it all, where his energy comes from, and what it’s like to be “post-chaos.” Then, we talked about art, content, and commerce, Patreon’s model (that isn’t actually pure patronage), and why Silicon Valley undervalues art, brand, and narrative — and Patreon. Jack shared the benefits of a business model that is fully aligned with creators, why he hates the word influencer, and why he’s still the right man for the job after 13 years of leading Patreon. We also covered what great leadership looks like, building fans and community, filmmaking, authenticity (from Charlie Kaufman to Prince), and remembering to take risks until the very end. I hope you’re inspired to make things you are proud of and to draw the next page even when you have no business doing so. While I have you: I’d strongly recommend Jack’s recent SXSW talk on AI, creativity, and change. -- Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion's new developer platform and workers here. You can learn more at notion.com/dialectic. -- Timestamps: (0:00) Opening Highlights (1:38) Intro to Jack & Thanks to Notion (3:44) Start: Prolific Output, Energy, Juggling, Endurance, and Becoming Post-Chaos (22:04) Combining Creativity and Business and Art vs. Content (33:21) Advertising vs. Membership & Patronage vs. Patreon (44:06) Jack's First and Only Job, and Silicon Valley's Undervaluing of Creativity, Brand, and Storytelling (and Patreon) (55:17) Building for Creators First, Incentive Alignment, Trust, 100 Years of Patreon, and Why Jack is the Right CEO for Now (1:04:49) Leadership: Types of Ambition, Obsession, Self Reflection, Bias to Action, Learning from Others (1:12:59) Talent vs. Enthusiasm, Being Proud of What You Make, Making Fans and Being True, Managing Parasociality, and Community (1:28:30) Filmmaking, Labels and Collectives vs Individuals, Breaking Patterns, Creative Intimacy, Music, Patreon's Origin, Persistence, Lucid Dreaming, and Taking Risks (1:49:26) Thanks Again to Notion
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  51: Nan Ransohoff - Power Laws for Philanthropy 14.07.2026 2j 11mnt

  Nan Ransohoff (X, Substack, Website) is Head of Public Goods and former Head of Climate at Stripe. This includes Frontier (which she co-founded): an advance market commitment that accelerates carbon removal by guaranteeing demand for it before it exists. They also recently launched Intercept Fund, a new effort to end respiratory infections, led by Nan and Charlie Petty. Nan has written extensively about Stripe’s efforts and philanthropy broadly, including her call for general managers for the world’s pressing problems, and on what she calls the third wave of American philanthropy. We talk about what a "Nan" is and why we need GM’s: ambitious founder-like people who obsess over an outcome and work backwards from it, wearing whatever hat the problem requires. We discuss taste in big problems, slicing them up and making them tractable, and why vision is in short supply. We also discuss the coming wave of new philanthropic dollars (est. ~$40B/year), primarily driven by The OpenAI Foundation, Anthropic Founders, and Anthropic employee matching, and how the ecosystem will need to mature to effectively deploy this much capital. Nan also reflects on her unlikely turn toward philanthropy and what it felt like to get off the ladder of a specific kind of ambition. We wrap up with a range of miscellanea and some fun debates. I hope you are inspired to notice problems you can’t ignore, be optimistic and specific about the world you hope for, and choose an (unlikely) path that you are proud of. Transcript and all links: https://dialectic.fm/nan - Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Watch here for more on Notion's new developer platform and workers. You can learn more at notion.com/dialectic. - Timestamps: (0:00) Opening Highlights (1:15) Intro to Nan (3:18) Thanks to Notion (4:53) Start: What is a Nan? Nerd-Sniped by Orphaned Problems (12:39) GMs, Seeing the Chessboard, and Working Backwards from Outcomes (18:55) Good Taste in Problems, Vision, and Good Finish Lines (35:43) Advance Market Commitments Tactically Solving Carbon Removal (41:35) Focus and Sketching Out or Slicing Up Messy Problems (49:39) Legibility, Public Rallying, and Ambition in Philanthropy (54:38) Third Wave Philanthropy and Hard to Quantify Problems (1:06:50) Risk Tolerance in Philanthropy and Scarcity of Funders and Allocators (1:15:22) The $40B Tidal Wave of New AI-Money and Why Start Now (1:19:53) Amount of Capital, Government Philanthropy, and Making Philanthropic Founders Rich (1:31:44) Nan's Mid-Career Inflection Point and Getting Off the Obvious Path (1:39:47) Grab-bag: Why Stripe Funds Public Goods, Making Things with Friends, Creative Partnership, Iceland Drone, and Scone Heads (1:49:39) Syllabi for the Squishy Topics & Study vs. Experience (1:57:01) Inputs & Outputs and GLPs for Attention (2:04:38) Closing: Interviewing Parents and Imagining an Obituary (2:09:58) Thanks Again to Notion
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  50: Tyler Cowen & Nabeel Qureshi - An Appetite For More 30.06.2026 1j 55mnt

  Tyler Cowen (Website, X, Marginal Revolution, Conversations with Tyler) is an economist at George Mason University, leads the Mercatus Center, and is the author of many books including The Great Stagnation and Average Is Over. He has blogged nearly daily at Marginal Revolution for over 20 years, has interviewed hundreds of world-experts on Conversations with Tyler, and runs Emergent Ventures, a prolific grants program that has funded multiple Dialectic guests. Nabeel S. Qureshi (Website, X, Substack) is an entrepreneur, writer, and researcher. He runs a stealth startup. Previously, he was a Visiting Scholar at Mercatus and spent nearly eight years at Palantir. He writes some of my favorite essays, including "What Makes Art Great" and "Rented Virtue", and was previously a guest on Dialectic for episode 13: "The Will to Care." Tyler and Nabeel are good friends, and given how prolific Tyler is, I decided to use Nabeel as an entry point and interview them together. We discuss sacred commitments, AI acceleration, mentorship, friendship, and more, but I focused the majority of the conversation on art and aesthetics. Tyler and Nabeel are unlikely aesthetes given their day jobs, but in fact take art deeply seriously. They have a shared love for and similar tastes in art, music, and film, in particular. We discuss strange and beautiful art, aesthetic stagnation, and a wide range of favorites: The Beatles, Mozart, Mondrian, Springsteen, Lana Del Rey, Kanye West, Cassavetes, The Sopranos, Apichatpong Weerasethakul, and more. Please enjoy, and thank you for supporting, listening, and watching through fifty episodes of Dialectic. I can't wait for the next fifty! Transcript and all links: dialectic.fm/tyler-nabeel --- Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion's new developer platform and workers here. You can learn more at notion.com/dialectic. Timestamps: (0:00) Opening Highlights (1:18) Intro to Tyler & Nabeel (3:02) Thanks to Notion (4:38) Start: Sacred Commitments, AI, Markets, and Acceleration (20:23) How Art Moves Us (27:08) "Beauty," Strangeness, Great Art, Music, and The Beatles (44:09) Film, Critics, Learning to Appreciate Depth, More Music, "Lowbrow" Art (1:02:25) New Aesthetics, Sources of Inspiration, Optimism & Pessimism (1:11:22) The Internet & Twitter's Virtue, Group Chats, and Cities (1:21:35) Mentors, (Possibly Quitting) Writing Books, Friendship (1:34:54) Interviewing, Identifying Talent, and Agency (1:47:21) Closing Questions (1:53:38) Thanks Again to Notion
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  49: Jasmine Sun - Close Enough to See Clearly 18.06.2026 2j 37mnt

  Jasmine Sun (Substack, X, LinkedIn) is an independent writer and journalist. She is a contributing writer for The Atlantic and also writes for other major publications, like The New York Times. She previously led core product at Substack. Jasmine focuses on Silicon Valley and AI, and is something of a participant observer, living among the strange and inspiring people pulling the future forward in San Francisco. In her writing, she plays to both sides: focusing on a more endemic audience with her newsletter while telling the broader world about what she learns in flagship pieces for major publications. Several of these anchor around memes that she thinks may deeply matter: “the permanent underclass,” “chinese peptides,” and “claude code psychosis,” to name a few. Jasmine has done many interviews about these individual topics, so I wanted to focus on her and her approach: playing to both audiences, her taste in questions and topics, doing both “serious” journalism and more personal writing, how going independent wasn’t so risky, what she admires in great writing, AI and her coming “AlphaGo moment,” China, and more. Please enjoy. --- Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion’s new developer platform and workers here. Check out Brian’s X/Twitter sync worker. You can learn more at notion.com/dialectic. Timestamps: (0:00) Opening Highlights (1:30) Intro to Jasmine (2:13) Thanks to Notion (3:24) Start: Being a "Historian of Vibe" and Learning to Look (15:00) Taste for Questions & The Depth Behind Memes (24:28) Translating Between Silicon Valley and The World (40:27) Substack vs. "Serious" Journalism and Integrity as a Writer (47:35) Integrity when Using AI and the AlphaGo Question (58:42) Strategy Across Publications & Maximizing an Idea's Reach (1:06:45) Going Independent, Risk, and Commercial Tradeoffs (1:24:35) Great Writing: Style, Voice, and Resisting Summary (1:35:35) Literary Inspirations, Favorite Essays, Writing vs. Thinking, and Getting Better (1:51:09) Writing to Publish, Authenticity, and Art (2:00:38) Grab Bag: China, Silicon Valley's Virtues and Problems, AI Transition, The Relational Economy, Parties, Debates, Self Belief, and More (2:35:16) Thanks Again to Notion Select Articles From Jasmine Silicon Valley is Bracing for a Permanent Underclass (NYT) ‘Chinese Peptides’ Are the Latest Biohacking Trend in the Tech World (NYT) Claude code psychosis (Substack) Notes on AI, labor, and China (Substack) America against china against america (Substack) The Human Skill That Eludes AI (The Atlantic)
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  48: Henri Stern - Principled Enough to Be Pragmatic 17.06.2026 1j 54mnt

  Henri Stern (X, LinkedIn) is the co-founder and CEO of Privy. Privy builds wallet infrastructure for developers, enabling them to let their users hold and use crypto, including stablecoins. Privy was acquired by Stripe in 2025, and remain an independent organization within the company. They work with large fintechs like Ramp and Klarna while also supporting some of the most notable crypto-native platforms like Hyperliquid. Henri also supports a number of other crypto efforts within Stripe. Henri is thoughtful, measured, and principled. Yet he is also pragmatic. He doesn’t like to play philosopher and yet he is one of my favorite people ask big questions about our future and our digital lives. Our conversation is anchored in the phrase at the bottom of Privy's website: "technical decisions are moral decisions." He and Asta Li started Privy to focus on user data privacy, and we talk about what digital privacy means and why it still matters. After realizing they were trying to serve the market something it didn’t want, Privy found an inflection point initially by enabling developers to embed crypto wallets in their apps. We talk about the painful decision to pivot, and later, to commit to both ends of the crypto market: hardcore, trading-oriented products and stablecoins as they flooded into traditional fintech infrastructure. We also talk about joining Stripe, what Crypto’s future looks like, and his level-headed mindset for our tumultuous future. All links and transcript available at dialectic.fm/henri-stern. --- Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion’s new developer platform and workers here. Check out Brian’s X/Twitter sync worker. You can learn more at notion.com/dialectic. --- Timestamps: 0:00 - Opening Highlights 1:40 - Intro to Henri 3:10 - Thanks to Notion 4:51 - Start: Technical Decisions are Moral Decisions 15:41 - Ambition, Startups, and Crypto 23:39 - Why Digital Privacy Matters: Self-Determination, Security, and Identity 41:52 - Embedded Wallets, the Pivot, and Privy's Core Bet 55:18 - Reinventing Around Stablecoins Without Abandoning Crypto-Natives 1:06:42 - Joining Stripe, Privy Today, and What Stripe Is Becoming 1:22:54 - Crypto's Future, Power Laws, Optimism and Pessimism 1:38:14 - Closing: Asta, Stripe's Leaders, Being French, and Never Compromising 1:52:48 - Thanks Again to Notion
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  47: Paul Scherer - A Friend That Brings Us Closer 27.05.2026 2j 16mnt

  Paul Scherer (X, LinkedIn) is the founder of Eigen (check out their beautiful website), where he’s building a mutual friend: an AI that brings people closer together and helps us belong. Paul grew up in a small town outside of Frankfurt, Germany, and dropped out of high school at seventeen to work on startups, including Augment. He recently raised $15M from Benchmark, with legendary partner Peter Fenton comparing him to the founders of Facebook, Twitter, Instagram, and Snapchat. I was introduced to him by Notion co-founder Akshay Kothari, who is an angel investor in Eigen. Dialectic guest Brie Wolfson has also been working with Paul, so I wanted to see what all the fuss was about, and why so many people I respect were so enamored with a kid who has yet to publicly launch a product. We start with Paul’s central influence: Michael Ende’s children’s novel, Momo, and the little girl who reminds a village to be present in the face of Time Thieves quietly pushing them to be more efficient. Then we talk about how even though the internet has shaped both of our lives and relationships, it increasingly feels that social media is making us feel both more connected and more alone. Paul explains what they are working on at Eigen, why we need an (AI) mutual friend, why it should be a single “person,” and why it feels less like engineering and more like parenting or growing someone/thing you don’t have complete control over. I also ask Paul about the pressures and psychology around being “blessed” by Silicon Valley’s powers that be, and why authenticity, or something like it, is in short supply. I hope you are inspired to be courageous in your convictions, even if they are strange, and to listen to the voice inside that so many of us stop listening to in adulthood. All links available at dialectic.fm/paul-scherer - Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion’s new developer platform and workers here. Inside Notion by Brie Wolfson & Camille Ricketts for Colossus. You can learn more at notion.com/dialectic. Timestamps: (0:00) Opening Highlights (1:13) Intro to Paul (2:33) Thanks to Notion (3:28) Start: 'Momo', Presence, Friendship, and Time (11:10) How the Internet Connects Us and Isolates Us, and Conflating Social and Media (25:12) A Future Where We Talk to AIs (33:55) Paul and Eigen are Building a Mutual Friend to Help Us Connect with Other Humans (48:01) Why Do We Need a Mutual Friend? And Making a Friend We Can Trust (1:16:53) Belonging, Building the team at Eigen, and Inventor as Outlaw (1:25:38) Managing the Psychology of Being a Promising Young Founder (1:36:53) Maintaining a High Bar, Fighting Entropy, and Influences (1:53:50) Self-belief, Authenticity, Seeing the Water (2:10:30) Courage, and a Final Question from a Mutual Friend (2:15:04) Thanks Again to Notion
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  46: Nicole Seah (Nix) - Loving What is Real 11.05.2026 1j 55mnt

  Nicole Seah (X, Substack, LinkedIn), aka Nix, is a writer at Starting From Nix and investor at Costanoa Ventures. She recently launched New Ontologies, where she profiles founders and companies thinking ambitiously about the future. Her first piece is live now, on Ando: the team building a chat platform for the era of agents. Nicole balances identities with poise, moving between the literary and the practical. I spoke to her about different kinds of beauty and how it takes us out of ourselves, Nietzsche’s case for tolerating strangeness, and choosing reality over fantasy. Then we discuss duality and balancing intensity and lightness, and talk through Borges, Hesse, Miyazaki, Alyssa Liu, and Joan Didion. Nicole argues that freedom comes from not collapsing yourself into a single identity. I asked her about the drive behind New Ontologies, her obsession with techne, and Rebecca Solnit's "cosmology of self.” We then skate across a range of ideas, including memory, appetite and desire, and friendship and why other people’s unknowability is part of what makes them wonderful. I hope this conversation inspires you to look for and love what is real, to be patient with and attuned to the multiple people inside you, and to give freely with your creative life. Full transcript and all links and references: dialectic.fm/nix. - Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. Inside Notion⁠ by Brie Wolfson & Camille Ricketts for Colossus. You can learn more at notion.com/dialectic. Timestamps: 00:00 - Opening Highlights 01:14 - Intro to Nicole 02:04 - Thanks to Notion 03:48 - Start: Beauty — Effort, Attention, Strangeness 19:59 - Fantasy and Reality 29:41 - Multiple Identities, Intensity, and Lightness 49:08 - New Ontologies: Profiling Founders Building the Future 1:08:57 - Memory, Lineage, and Process 1:18:41 - Appetite and Honesty 1:23:47 - Friendship, Proximity, and The Unknowability of the Other 1:41:18 - Closing Notes: Solitude, Noticing, and Generosity 1:53:40 - Thanks Again to Notion
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  45: Nicholas Thompson - A Life of Long Form 28.04.2026 1j 54mnt

  Nicholas Thompson (Website, X, LinkedIn, Wikipedia) is the CEO of The Atlantic, an elite distance runner, and the author of The Running Ground—a memoir about his father, his life, and the sport of running. Full transcript and all links at dialectic.fm/nick-thompson. Nick has led The Atlantic to tremendous subscriber growth and profitability since joining the then-money losing publication in early 2021. He was previously editor-in-chief of WIRED and editor of newyorker.com. He also co-founded The Atavist, wrote The Hawk and The Dove, and is a prolific interviewer, including his latest series, The Most Interesting Thing in AI. Nick is also the American record holder in the 50K, which he re-broke two days after we recorded this conversation (Exhales). We talked about the future of words in the age of AI, what makes a journalist, why legacy media institutions like The Atlantic are worth fighting for, and what great editing and coaching have in common. Then we turned to running and life: the small tailwinds that compound beyond what we can imagine, Nick’s trajectory—through a prodigious start, early career failure and African kidnapping, cancer at 30, and wild success since—to name a few beats, the trials and blessings of inheritance, and the versions of himself he may no longer have time to find. To close, Nick honors Scott Thompson’s memory by sharing how we might all be more like him and reflects on what drives aliveness. I hope you are inspired to get started, feel the wind at your back, clear unexpected hurdles, savor great words, raise your bar beyond what is reasonable, be grateful for those who came before and pay it forward to those who are next, and remember that there is always more waiting—for you, for me, for us. P.S. It’s unrelated to this conversation, but please read The Atlantic’s latest cover story and one of my favorite (and funniest) things I’ve read in ages. Caity Weaver on The Best Free Restaurant Bread in America. Long live long form writing. - Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic. Timestamps: 0:00 Opening Highlights 1:17 Intro to Nick 2:24 Thanks to Notion 3:30 Start: Words, Reading, and Writing in an Automated World 18:39 Why Stories Matter and What Makes a Journalist 28:22 Media Institutions, The Atlantic, Democracy, Tech, and Power 44:21 Retaining Great Writers and The Virtues of Editors (and Coaches) 57:44 Magazines and America 1:05:57 Running, Motivation, Momentum, and Tailwinds 1:16:08 Aging, Fathers and Sons, Inheritance, and a Mother's Grace 1:31:00 Merging Machine-like Discipline and Wild Curiosity, The Boat that Never Touched Water, and Who We Might Still Become 1:44:11 Gratitude, Stalin's Daughter, Scott Thompson's Verve, and Feeling Most Alive 1:52:40 Closing and Thanks Again to Notion Key Links: The Running Ground - Nick Thompson Why I Run (excerpt from Running Ground) - Nick Thompson for The Atlantic Not Fade Away book - by Laurence Shames and Peter Barton Nick Thompson - Timeless (With Guarav Ahuja) Writer Evan Ratliff Tried to Vanish: Here's What Happened (Wired) John W. Gardner — "Personal Renewal" Speech Will the Humanities Survive Artificial Intelligence? - D. Graham Burnett for The New Yorker
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  44: Jared Weinstein - Within Earshot, Out of Camera Shot 20.04.2026 2j 50mnt

  Jared Weinstein (LinkedIn, X) is an investor, advisor, civic leader, and founder of Overton. This is his first interview. Full transcript and all links at dialectic.fm/jared-weinstein. Jared spent his twenties in the George W. Bush White House, starting as a scheduling intern and rising to become the President's personal aide. He went on to Stanford GSB, consulted for Palantir in its early days, and was a founding partner of Thrive Capital in NYC, helping build it into one of the most respected venture firms in the world over eleven years. After leaving Thrive in 2022, Jared returned to Birmingham to focus on Overton, where he invests in local founders, leads civic initiatives including Small Magic — an early childhood language development program — and works to make his hometown the best version of itself. He also continues to invest in startups, serve on boards, and seed and advise new investors. By his own words, he is busier than ever. Despite his very serious resume, anyone who knows Jared will tell you that he radiates humanity. He has spent his career amplifying people and helping them become the best version of themselves. We trace the arc of his career, talk about what it's really like inside the Oval Office, what he admires about the President, and the unlikely pivots that led him beyond a prodigious start. We also discuss what he and Josh got right at Thrive in the early days, how high stakes environments can be psychologically safe, and how to support incredibly ambitious people. Then we talk about his theory of change for Birmingham, the work he is doing now, and his reflections on where he's been and what he'd like to be known for. I hope this conversation gives you a model for what it looks like to bring your full humanity into high-stakes work and inspires you to commit yourself to the people, institutions, and communities you believe in. - Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic. - Timestamps 00:00 - Opening Highlights 01:40 - Intro to Jared 03:32 - Thanks to Notion 04:38 - Start: Being a "Friend" and Bringing Humanity to Serious Work 10:55 - From Duke to the West Wing 31:45 - Riding Shotgun with President Bush 59:27 - Starting Over Out West: Post-WH, Stanford, and Palantir 1:16:05 - Meeting Josh Kushner and Building Thrive Capital 1:44:37 - Founders, Humility, and the Three-Body Problem of Ego, Ambition, and Impact 2:06:41 - Leaving Thrive, Coming Home to Birmingham, and Overton 2:32:40 - Busier Than Ever: Mentors, Life in Acts, and What You Hope to Be Known For 2:49:11 - Thanks Again to Notion
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  43: Mario Gabriele - Reality is Story-Shaped 07.04.2026 1j 48mnt

  All links and transcript at dialectic.fm/mario-gabriele Mario Gabriele (X) is a writer, investor, and analyst. He is founder of The Generalist and Partner at Hummingbird. He aims to bring the rigor of investment analysis with writing quality and style that is closer to the New Yorker. His profiles, deep dives, and briefings are amongst the highest quality writing in the technology business, and he interviews practitioners weekly on his podcast. Recently, he wrote the definitive (and nearly book-length) piece on Peter Thiel’s legendary investment outfit, Founders Fund, and profiled Microsoft’s Satya Nadella. I spoke to Mario about stories and the truths they hold or reveal. He is a writer first, and it shows in his prose, style, and depth. We also discussed the evolution of The Generalist’s content and business model, both of which he has experimented with ruthlessly. The subscription counts 160,000+ readers / listeners and is currently ranked as the #7 bestseller in Substack’s business rankings. He is also an investor focused on the technology world’s heroes: founders. Hummingbird, which he joined earlier this year, is known for its obsessive approach to understanding the minds, motivations, and worlds of the entrepreneurs it backs. We dive into the under-discussed elements that shape world-beaters, including the notion that ambition almost always comes from some level of pain. Across the conversation, we talk about how authenticity and evolution run across his career, and how he is at peace as someone who doesn’t know exactly who he is becoming. That generalist orientation continues to produce unlikely paths that surprise him. I hope this conversation inspires you to take stories seriously, to look for what's true beneath the polished surface, and to trust paths you didn't plan for. Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic. Timestamps: (0:00) Opening Highlights (1:13) Intro to Mario (2:49) Thanks to Notion (3:58) Start: Stories, Truth, Writing, and the Story Beneath the Story (23:39) Failure, Authenticity, Comparative Advantage, and The Most Annoying Aphorism in the World (35:55) The Generalist's Style (45:20) Process, Goals, Vision, Experimentation, and Business Models (57:52) Investing: Energy, First Checks, Notecard-level Clarity, and Peter Thiel (1:07:46) Understanding Founders, Motivation, Good and Bad Fuel, and True Ambition (1:17:47) Hummingbird: Seeing the World as it Actually Is and How Stories Reveal Truth, Linguistics, Observation, Deciding to Join, and Evolution (1:29:32) Motivation, Raising the Bar, Ongoing Learning and Teachability, Status, Unlearning, Generous Products, and The Reward of Not Knowing (1:47:15) Thanks Again to Notion
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  42: Celine Nguyen - Nurturing Your Mind in Public 30.03.2026 2j 19mnt

  All links and transcript available at dialectic.fm/celine-nguyen Celine Nguyen (Website, Substack, X) is a writer, software designer at Watershed, and literary critic. She writes personal canon, a newsletter about literature, design, art, and technology that has grown to tens of thousands of subscribers. She has also written for The Atlantic, Asterisk Magazine, and more. I discovered Celine with her reflection on two years of writing her newsletter, where she made the case for living a life of the mind, reading great things, and writing online: "After 2 years, I’m convinced that reading and writing are the most dignified and worthy activities that anyone can do—and, in fact, are activities that everyone should do." She also has written viral essays on research as a leisure activity and a case for reading Marcel Proust’s 3,000 page novel, In Search of Lost Time. In another favorite, she critically analyzes the mechanics of how great writers begin. Celine makes intellectual life and very serious books feel accessible and exciting rather than obligatory. We spoke about much of her writing, taking your intellectual growth seriously outside of academia, and how she has become an influencer in a good way. She believes you can expand the market for what you love, and her success is evidence that there is a market for more than the low-hanging fruit that dominates much of the internet. Celine sees reading and writing through the lens of becoming, and I was inspired to raise my own bar. I hope you can say the same. --- Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic, and check out their latest round of updates here. --- Timestamps: (0:00) Opening Highlights (1:35) Intro to Celine (4:25) Thanks to Notion (6:18) Start: Pursuing a Life of the Mind, Personal Curriculum, and Contextualizing the Present in History (24:53) Research as a Leisure, Self-Cultivation, and Calibrating Rigor (39:59) Effectiveness, Tools & Process, and Letting Output Drive Your Learning (59:35) Parasocially Influencing People to Do Good Things (Like Reading and Writing) (1:09:39) Drawing the Reader in and Expanding the Market for What You Love (and for Proust) (1:24:07) Aspiration, Posing, and Pretending Your Way into Enthusiasm (1:34:37) Preparation is Not Progress (1:46:07) Copying, Writing Process, Mechanics, and Design (1:57:25) Commitment, Finishing, Substack, Life Extension and Closing (2:18:31) Thanks Again to Notion
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  41: Henrik Karlsson: Strolling Through Life's Labrynths 23.03.2026 2j 42mnt

  Transcript and all linked references: https://dialectic.fm/henrik-2 Henrik Karlsson (Substack, X) is a writer and essayist. His newsletter, Escaping Flatland, explores attention, agency, relationships, and the inner life of making things. He is one of my favorite essayists, and I spoke to him previously on Dialectic 19: Cultivating a Life that Fits in Spring 2025. We met again in Copenhagen, this time on video. Our first conversation focused on designing your life iteratively and relationships. This time is about the messiness of creativity and problem-solving. We circle a central theme of navigating through the woods of confusion when you are—and must necessarily be to grow—lost, and trusting yourself to reach clarity on the other side. Henrik walks us through how he (and so many of his favorite artists and thinkers, from Brian Eno to Charles Darwin to Ingmar Bergman) smashes apart his mental models in pursuit of seeing things more clearly. Or at the very least, offering up something new. He also challenges my praise of boredom, describes how a ballerina finding balance in her body mirrors what creatives must do, likens desire to the energetic discovery of wandering (or dérive, like past guest Cyan Banister has spoken about), explains why the best art is like a Jenga tower, and reflects on what he believes in; Henrik’s humanity is on display. He challenged me to think much more ambitiously about the risks I take, the ways I am holding on to faulty models of reality, and how living richly is simply a matter of perspective. - Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams create their best work. Notion recently launched custom agents: helpful AI teammates that handle recurring work across your entire suite of tools. Automate you and your team’s repetitive tasks so you can focus on the deep work. You can learn more at notion.com/dialectic. Timestamps: (00:00) Opening Highlights (01:28) Intro to Henrik (04:05) Notion (05:58) Begin: Attention, Boredom, Predictability, Aliveness, and Dérive (14:52) Confusion and Clarity: Mental Balance, Breaking Mental Models, and Making It Through the Woods (31:37) Henrik's Notebooks, Personal Constraints (40:54) Introspection as Subject, Not Object: Nick Cave, Rick Rubin, and Attending Outward (46:56) Creative Risks, Constraints, and the Labyrinth: Eno, Von Trier, Cage, and Herzog (1:03:47) Agency, The Right Kind of Risk, and What Else Is Possible (1:23:29) Desire: Trusting Excitement and "Galloping Down the Street" (1:30:44) Why Good Ideas Come from the Edges and Keeping the Space to Sit in Your Ideas (1:44:58) Physical Space and Isolation (1:51:19) Jenga Towers: Why Great Art Has Space and Spits You Back Out (2:01:30) Conviction, Belief, Navigating Murkiness with Firmness and Openness (2:15:54) Short Essays and How Reading Is Like Running (2:22:27) What Love Is Like and Befriend Those We Read (2:29:18) Grandfather Nils and a Final Reminder (2:40:49) Thanks Again to Notion
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  Independent Study: Body Futurism by Toby Shorin (Essay) 15.03.2026 34mnt

  A new experiment: I thought it would be fun to share audio versions of essays or writing from past or future Dialectic guests. Toby Shorin (ep. 7: The Shapes of Culture) recently published 'Body Futurism,' a piece based on a talk I heard him give in 2024 and that I loved. You can read this piece at https://writing.tobyshorin.com/body-futurism/. It is provocative and feels increasingly prescient. Toby suggests that we must return to the body—and not just bodies in theory but quite literally your, my, our physical bodies, as the starting point for how we think about what is good for how we live and how we design and improve our societies. It was published Feb 25, 2026. I'm calling this format Independent Study. You can think of it as curated audiobook versions of internet writing. We'll see if I do more of these, and feedback is welcome. But let me know what you think!
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  40: Charles Broskoski - Everything is Personal 25.02.2026 2j 29mnt

  All links and transcript: dialectic.fm/cab Are.na channel for this episode: are.na/jackson-dahl/dialectic-cab Charles Broskoski (Website, Are.na, X), aka Cab, is an artist turned entrepreneur and co-founder & CEO of Are.na, a platform for collecting, connecting, and self-directed learning. I created an are.na channel for all of the references I used in preparation for this episode. Charles began as an artist before becoming a software engineer, and started Are.na with many collaborators out of a desire to replace the now defunct del.icio.us after it was acquired by Yahoo. He and a range of collaborators have been working on Are.na for nearly 15 years, and he is now focused on it full-time, thanks to the platform’s 18,000 paying subscribers. While I’m not a longtime Are.na user, I discovered Charles by way of his talk / essay, “Here for the Wrong Reasons” and was enthused by his philosophy of attention and how the things we encounter shape us. Our conversation centers on patterns of noticing and what it means to know yourself through what you pay attention to, or as Charles calls it, your radar. We discuss creativity as decision-making, self-directed learning and research, and Are.na's channels as frames for what we encounter. We also talk about personal versus performative taste, opinionated design that still gives you space, building something that lasts, and why Charles believes creative people should start deeply personal businesses. I hope you are inspired to be generous and scrutinizing with your attention, to create things that are personal and durable, and to remember that knowing yourself is a worthy journey of a lifetime. - 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 where you can find all links and transcripts. You can learn more at notion.com/dialectic. Special thanks to Earshot in NYC for hosting us for this conversation. Timestamps (0:00) - Opening Highlights (1:21) - Intro: Charles Broskoski (4:00) - Thanks to Notion (5:26) - Start: Creativity as Self-Knowledge and Problem-Solving (13:37) - Self-directed Learning and Casual Research (21:33) - Skateboarding, Being a Beginner, In Defense of Posers (33:26) - Contextual Patterns and Channels (45:54) - Nodal Points, Your Radar, and Careful Attention (1:04:57) - Subjectivity, Self-Knowledge, and Taste (1:15:09) - Performance: Here for Fame and Not Love (1:22:53) - Aspirational Attention (1:29:02) - Designing Generous Tools (1:42:44) - Space in a Product and Fading into the Background (1:50:01) - Why Creatives Should Be Entrepreneurial & Building an Independent Business Online (1:54:11) - Patience, Durability, and Antifragility (1:59:48) - Personal Businesses (2:10:27) - Grab Bag: Authenticity, Bohm Dialogue, Skateboarding, and Keeping Things Personal (2:28:28) - Thanks Again to Notion
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  39: Andrew Reed - Don't Flinch 11.02.2026 2j

  Full transcript and links: https://dialectic.fm/andrew-reed. Andrew Reed (X, Website, Sequoia) is a growth investor at Sequoia Capital, where he has invested in companies including Robinhood, Figma, Klarna, Phantom, Vanta, and ElevenLabs. He is quietly one of the best growth investors of his generation. We begin with how Andrew's competitiveness and humanity coexist—the twin brother rivalry, the football player who also did musicals, the Goldman analyst who came to value people over spreadsheets. He also shares how an early lack of confidence helped him become a great observer of people and situations. We talk through his approach to investing: why spreadsheets are “always wrong” in one direction, how he underwriters revenue growth, and what he sees in the world-beaters he invests in. We discuss several of his most formative investments—Robinhood as a 27-year-old’s first check, and again during the first week of COVID; Figma at a price people thought was insane; and a 14-second conviction on Vanta’s—and what each taught him about conviction, timing, and not flinching. Andrew shares his perspective on serving as a board member, knowing when to double down, closing deals, and how craft can be a commercial input. We also talk extensively about Sequoia Capital and its legendary leaders, from Don Valentine, to Doug Leone and Mike Moritz, to newly-appointed Co-Steward Pat Grady. Andrew reflects on what it means to apprentice at an institution where greatness is the expectation and the champagne toast lasts five minutes. I hope this conversation inspires you to show up ready for the day you don't expect, to rise to the stakes rather than shrink from them, and to move through your life and work a little more lightly. - 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 this 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 (2:02) - Intro: Andrew Reed (3:50) - Thanks to Notion (5:23) - Start: Humanity, Spotting Weird, and Competitiveness (19:07) - Investing & Great Founders (37:53) - Andrew's Style, Pat Grady, and Continuous Learning (47:31) - Doubling Down and Not Flinching (56:09) - Empathy on Boards, Learning the Real Business, "Expensive" Prices, and Selling (1:07:18) - Managing Ego and Becoming a Leader (1:14:08) - Craft as a Commercial Input, Knowing vs. Feeling, Preparing for Big Days, Becoming a Great Closer (1:28:39) - Sequoia Capital (1:38:57) - Don Valentine, Mike Moritz, and Doug Leone (1:51:29) - Closing Questions (1:59:08) - Thanks Again to Notion
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  38: Molly Mielke McCarthy - The Art of Peopling 29.01.2026 2j

  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
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  37: Trevor McFedries - Creative People Should Be Rich 20.01.2026 2j 18mnt

  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.
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  36: C. Thi Nguyen - Measurement, Meaning, and Play 13.01.2026 2j 21mnt

  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