Podcast
Dialectic
Hosted by Jackson Dahl · EN
Conversational portraits of original people, across technology, media, business, and creativity. By Jackson Dahl.
25episodes
Episodes
Newest firstAll episodes
46: Nicole Seah (Nix) - Loving What is Real
6d ago01:55:13Summary readyNicole 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
3w ago01:54:17Summary readyNicholas 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
4w ago02:50:07Summary readyJared 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
Apr 701:48:11Summary readyAll 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
Mar 3002:19:24Summary readyAll 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
Mar 2302:42:03Summary readyTranscript 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)
Mar 1500:34:08Summary readyA 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
Feb 2502:29:58Summary readyAll 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
Feb 1102:00:00Summary readyFull 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
Jan 2902:00:00Summary readyTranscript 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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