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64 afleveringen, van nieuw naar oud
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61: Josh Miller - A Good Rectangle
22 oktober 2026 · 1 uur 54 min
Josh Miller (X, LinkedIn) is co-founder and CEO of The Browser Company, makers of Dia and Arc. The Browser Company was acquired by Atlassian last year. Lees meer
Before The Browser Company, Josh was an investor at Thrive Capital, Director of Product in the Obama White House’s Office of Digital Strategy, and co-founder of Branch, which was acquired by Facebook.
He studied sociology and has always been thoughtful about environments: institutions, companies, and digital and physical spaces. We talk about his effort to improve the space many of us spend our days in: the browser. We discuss the tension between Josh’s creative and commercial instincts, optimizing for feelings, and hiring unlikely stars. Josh reflects on much of the journey with Arc and Dia and why he’s still betting on the browser in the AI era, now as part of Atlassian.
I hope you are inspired to believe in people and leave your fingerprints on what you create.
Full transcript & links: https://dialectic.fm/josh-miller
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Dialectic is presented by Notion. Notion is a collaborative workspace for your life’s work and a hub for all the context you and your team use to work with each other and with AI. New models are available in Notion the day they launch, and you can work with agents you build in Notion or any other agents and tools you already use. As tools change, Notion is the Switzerland in the middle that keeps your context consistent across all of them. Learn more at notion.com/dialectic.
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Timestamps:
(0:00) Intro: Josh Miller
(1:55) Start: Not Commercial Enough & Optimizing for Feelings
(9:14) Sociology, the Obama White House, Thrive, and the 5% Favicon
(15:38) Bowling Alone, James Turrell, and Roden Crater
(22:12) Betting on People, Leaving Thrive, and Where Computing Goes
(34:54) “Assume You Don’t Know” and What Was Sacred at The Browser Company
(41:58) Intuition, Road Trips, and Leaving Fingerprints on Things
(53:57) Building in Public, Pulling Back, and the Road to Atlassian
(1:03:23)…
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60: Patrick Hsu - Speedrunning the Infinite Game
15 oktober 2026 · 1 uur 56 min
Patrick Hsu (X, Website, Arc lab) is co-founder and core investigator of Arc Institute, assistant professor of pathology at Stanford, and venture partner at Thrive Capital. Lees meer
Patrick has always been precocious: he began college as a young teenager and contributed to early CRISPR-Cas9 gene-editing breakthroughs as part of Feng Zhang’s lab at the Broad Institute of MIT and Harvard. Today, the Hsu Lab at Arc works where genome engineering meets AI, from bridge recombinases that can rearrange up to a million bases of DNA at once to Arc's Evo biological foundation models.
We discuss Patrick’s pace and ambition, infinite games, and why he was drawn to biology. Then, we traverse power laws in biotech and the reach of GLP-1s, research taste and success, Arc’s multidisciplinary model, data limits in AI-enabled bio, and cell and bio foundation models. We also discuss how AI and new science will help us solve diseases, design life, and push the boundaries of sci-fi when it comes to human health. I hope you are inspired to raise your bar, commit to reinvention, and hold a lightness that makes the long and challenging journey fun.
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Dialectic is presented by Notion. Notion is a collaborative workspace for your life's work, and it works with whatever AI you use. New models are typically available in Notion the day they launch, you can tag agents from inside Notion, and you can tag Notion from your other AI tools. As the tools around you change, Notion stays the one place that holds your context. Notion is also hiring across product, engineering, design, storytelling, and more. Learn more at notion.com/dialectic.
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This episode is supported by Google. Gemini 4 Argon recently launched and is built for long-horizon work. I used it inside Antigravity and gave it all 60 Dialectic transcripts: more than a million words. Instead of summarizing episodes one by one, Argon synthesized across them, tracing how ideas from early conversations connect to later ones. Together we made T…
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59: Joe Gebbia - Design We Deserve
8 oktober 2026 · 1 uur 50 min
Joe Gebbia (Website, X, LinkedIn, Wikipedia) is the first U.S. Chief Design Officer, leading the National Design Studio. He is also the co-founder of Airbnb and Samara. Lees meer
The NDS and this role were created by executive order of President Trump in August 2025. I met Joe Washington, D.C, to reflect on the past year and talk about bringing the care and ambition of great product design to the digital services that every American uses. Joe & NDS just launched America.gov, their flagship project of the last year: the central entry point for how Americans get what they need from the government.
Joe believes that design is how you respect and value the people who use a product or service. At Airbnb, that meant helping strangers feel comfortable in each other’s homes. In government, it means refusing to accept a low bar for the websites and processes that Americans use to interact with the government.
We begin with CritBuns, Joe’s RISD project that taught him that design is as much about storytelling as it is about product. Then, we discuss what he learned about designing for trust at Airbnb and his initial work at DOGE, streamlining and digitizing the federal retirement process. Joe walks me through America.gov, a single, AI-powered front door to government services. We discuss the challenges of scale and designing for people who are skeptical of both government and AI, including what it means to pass the “grandma test.” We wrap up with why ambitious technologists should aspire to work in government and his collaboration with Airbnb co-founders Brian Chesky and Nathan Blecharczyk.
I hope this conversation raises your expectations for the things we’ve learned to tolerate, and inspires you to think about how you might serve your community or your country.
Full transcript & links at dialectic.fm/joe-gebbia
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Dialectic is presented by Notion. As new models and agents arrive constantly, Notion acts as a context and consolidation layer for all the ways you and your team w…
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58: Adam Mastroianni - Let Me Be Useful
1 oktober 2026 · 2 uur 6 min
Adam Mastroianni (Website, X) is an experimental psychologist and the writer of Experimental History. He earned his PhD in psychology at Harvard before leaving academia to pursue research and writing independently. Lees meer
I first came across Adam through “Good conversations have lots of doorknobs,” which remains one of my favorite essays on Substack.
We talk about why psychology is stuck, why science needs people willing to look stupid, and how prestige can lead you toward a life you don’t want. From there, unpack Adam’s coffee bean test for figuring out what to do, getting “de-bogged,” and what improv teaches us about better conversations (or: create doorknobs). We also discuss writing that surprises its author, his upcoming book, The Strangest Idea in the World, and the prayer he says before publishing: “Let me be useful.”
I hope you leave a little more willing to question what seems obvious, risk looking stupid, and spend your time in ways you actually enjoy.
Transcript & links: https://dialectic.fm/adam-mastroianni
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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion AI works across your documents and context, while custom workers can automate recurring tasks and connect with your other tools. You can also explore Notion’s Knowledge Board, which evaluates how AI models perform on real knowledge-work tasks. Learn more at notion.com/dialectic.
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This episode is supported by Google. Google Antigravity is Google’s agentic development platform. Describe what you want to build, and its agents can plan the work, write and run code, and test the result, with plans and changes you can review along the way.
Gemini 3.5 Transcribe turns audio into text with a choice of verbatim and Smart modes. Verbatim mode keeps fillers and false starts, and supports speaker labels and word-level timestamps to help you check the transcript against the recording. Smart mode removes filler words …
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57: Immad Akhund - The Art of Irrational Effort
24 september 2026 · 2 uur 1 min
Immad Akhund (X, LinkedIn) is the co-founder and CEO of Mercury. He is also a prolific angel investor and co-hosts the Founders in Arms podcast. Lees meer
Mercury is a fintech banking platform used by one in three startups. It is Immad's fourth company in 20 years of entrepreneurship. Mercury is in the process of becoming an FDIC-insured bank and recently launched Mercury Books, AI-powered accounting software.
Immad grew up in Pakistan, moved to London at nine, and left for San Francisco at 23 to become an entrepreneur "for real." Mercury is built on something rare in finance: a willingness to spend a disproportionate amount of energy on details, the kind of care Immad admits "seems irrational.”
We start with a simple question (what is a bank?) and discuss why banking stayed bad for so long, what stays hard as AI makes software easy to build, and why Mercury's motto is "be extremely helpful." Entrepreneurship has shaped Immad's life, and he hopes Mercury can empower a generation of entrepreneurs.
I hope you come away a little more annoyed by the mediocre things we've all learned to tolerate and inspired to put an irrational amount of care into making them better.
https://dialectic.fm/immad-akhund
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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. It works with all of your agents and keeps context across them and your team. Check out the new Notion Skills API. You can learn more at notion.com/dialectic.
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Timestamps:
(0:00) Opening Highlights
(1:50) Intro: Immad Akhund
(4:16) Start: Banks and Why Immad Was Suited to Build One
(20:30) What Traditional Banks Do Well & What Mercury Got Right
(29:33) Why Mercury Wants a Bank Charter
(35:57) What's Scarce When Software Is Easy
(49:00) Becoming the Default for New Entrepreneurs
(53:34) Product: 100 Little Things Better
(1:06:51) The Right to Win
(1:09:19) Brand as Care
(1:15:19) Culture and Being Extremely…
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Independent Study: Personal Renewal by John W. Gardner (Speech)
16 september 2026 · 30 min
Independent Study is a series of bonus episodes to accompany the interviews on Dialectic. I read essays and other writing that has influenced me. Lees meer
"Personal Renewal" was given as a speech by John W. Gardner to a group at McKinsey & Company in Phoenix, AZ on November 10, 1990. The transcript is available at PBS here.
John W. Gardner was a public servant, educator, and public reformer. Learn more at PBS.
This is one of my favorite things I've ever read. I hope you are similarly inspired.
Transcript and audio for the also mentioned David Foster Wallace's "This is Water" available here, from Farnam Street.
https://www.pbs.org/johngardner/sections/writings_speech_1.html
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56: Miles Grimshaw - Back Down the Mountain
1 september 2026 · 1 uur 53 min
Miles Grimshaw (X, LinkedIn) is an investor at Thrive Capital. He’s spent most of his career there, there, partnering with founders at the early stages of company building, including Cursor, Turbopuffer, Chai Discovery, Mesh Optical, Revel, XDOF, Socket, Benchling, GitHub, and many more. Miles was also briefly an investor at Benchmark before returning to Thrive in 2024. Lees meer
The conversation focuses on Miles’ appetite for change and continuing to begin anew, again and again. That starts with “adventure racing” as a teenager, and continues through his career as an investor in search of world-changing companies.
We talk about how Miles proactively puts himself in position to work with great founders in a style that resembles courtship, his disposition of impatient patience, and why he loves change. The latter includes the dramatic shift in his primary domain: software. As the underlying assumptions for software businesses change due to AI, what traits will great companies have? And what moats if any will persist? Is software investing over?
Miles also talks through how great companies and founders go where they are looking, prioritizing customers that help you live in the future, the learned intuition of greatness, and joining the expedition squad alongside the founders Thrive partners with. Finally, we talk a bit about Thrive, his departure to and return from Benchmark, and endurance.
I hope you are inspired to find an infinite game where you are excited to see the stone roll back down the hill and begin to push again.
Transcript & links available at https://dialectic.fm/miles-grimshaw
Disclaimer: This podcast is for informational purposes only. The views expressed are the speaker's own as of the recording date and are subject to change. Thrive funds and their affiliates have investments in certain companies discussed in this episode. References to those companies are illustrative, do not represent all investments made by Thrive, and should not be viewed as recomme…
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Independent Study: Art is For Seeing Evil by Agnes Callard (Essay)
25 augustus 2026 · 27 min
“Art is For Seeing Evil” was published by Agnes Callard for The Point Magazine on July 15, 2022. My thanks to Agnes and The Point for permission to share this audio version of her essay on Dialectic’s feed. Lees meer
https://thepointmag.com/examined-life/art-is-for-seeing-evil/
Agnes Callard (UChicago, Substack, X, Wikipedia) is a professor of philosophy at The University of Chicago, focused primarily on ancient philosophy and ethics. She also writes for The Point, The New York Times, and more. I particularly enjoyed her recent conversation with Derek Thompson on her theory of the “uni-context.”
This essay was shared with me by Nan Ransohoff, (Ep. 51). I hope you enjoy it!
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55: Dan Lilienthal & José Chayet - As [untitled] as it Comes
18 augustus 2026 · 2 uur 10 min
Dan Lilienthal (X, LinkedIn) and José Chayet (X, LinkedIn) are childhood friends and cofounders of [untitled] (X, Instagram), a platform for musicians that they describe as a sacred place for work-in-progress music. It is where a song lives between recording and streaming. [untitled] is closer to the Photos app than to a social network: a private place to store, listen to, and slowly share demos, with no feed. Lees meer
Dan and José are not trained musicians, engineers, or designers, but they have built a product artists love by “method acting” their way into deep empathy. The platform has grown to 50K paying users and now allows artists to share unreleased music directly with fans. Lorde recently released XRAYS on [untitled]: 49 demos and works in progress from her album Virgin, creating a kind of museum behind the record.
We discuss music as a form of communication and a connection to the divine; why they have resisted adding a feed; product inspirations like the iPod and Snapchat; how empathy and QA underpin their product philosophy; designing for 16-year-olds and superstars; AI as an instrument; which parts of the creative process are worth sharing; what it means for software to be sacred; and building a company with your best friend.
I hope you’re inspired to consider what is sacred, share and live with the things you make, seek out music that inspires you, and stay untitled a little longer than is comfortable.
Full transcript and all links: dialectic.fm/untitled
This episode on [untitled].
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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.
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Timestamps:
(0:00) Opening Highlights
(1:24) Intro to Dan & José & Thanks to Notion
(4:42) Start: Brackets, How Creativity Makes the World Bigger, and Music's Connection to the Divine
(20:40) Duchamp, Music as a Set of Choices, and The Museum Behind the Work
(27:52) [untitled]: A Medium for M…
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54: Ian Rogers - Never a Spectator
18 augustus 2026 · 2 uur 37 min
Full transcript and all links and references: dialectic.fm/ian-rogers. Lees meer
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…
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53: Zhengdong Wang - Feeling the Wave
29 juli 2026 · 2 uur 8 min
Zhengdong Wang (Website, X, LinkedIn) is an AI researcher based in London. Lees meer
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
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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.
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Timestamps:
(0:00) Opening Highlights
(1:16) Intro to Zhengdong & Thanks…
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52: Jack Conte - Draw the Next Page
21 juli 2026 · 1 uur 51 min
Full transcript and all links: dialectic.fm/jack-conte Lees meer
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.
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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.
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Timestamps:
(0:00) Opening Highlights
(1:38) Intro to Jack & Thanks to Notion
(3:44) Start: Prolific Output, Energy, Juggling, Endurance, and Becomi…
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51: Nan Ransohoff - Power Laws for Philanthropy
14 juli 2026 · 2 uur 12 min
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. Lees meer
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
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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.
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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, a…
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50: Tyler Cowen & Nabeel Qureshi - An Appetite For More
30 juni 2026 · 1 uur 56 min
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. Lees meer
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
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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:
(…
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49: Jasmine Sun - Close Enough to See Clearly
18 juni 2026 · 2 uur 37 min
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. Lees meer
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.
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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,…
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48: Henri Stern - Principled Enough to Be Pragmatic
17 juni 2026 · 1 uur 55 min
Henri Stern (X, LinkedIn) is the co-founder and CEO of Privy. Lees meer
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.
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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.
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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, Sta…
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47: Paul Scherer - A Friend That Brings Us Closer
27 mei 2026 · 2 uur 16 min
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. Lees meer
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
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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 n…
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46: Nicole Seah (Nix) - Loving What is Real
11 mei 2026 · 1 uur 55 min
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. Lees meer
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.
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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, Intens…
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45: Nicholas Thompson - A Life of Long Form
28 april 2026 · 1 uur 54 min
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. Lees meer
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.
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44: Jared Weinstein - Within Earshot, Out of Camera Shot
20 april 2026 · 2 uur 50 min
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. Lees meer
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.
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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together…
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43: Mario Gabriele - Reality is Story-Shaped
7 april 2026 · 1 uur 48 min
All links and transcript at dialectic.fm/mario-gabriele Lees meer
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: helpfu…
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42: Celine Nguyen - Nurturing Your Mind in Public
30 maart 2026 · 2 uur 19 min
All links and transcript available at dialectic.fm/celine-nguyen Lees meer
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.
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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.
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Timestamps:
(0:00) Opening Highlights…
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41: Henrik Karlsson: Strolling Through Life's Labrynths
23 maart 2026 · 2 uur 42 min
Transcript and all linked references: https://dialectic.fm/henrik-2 Lees meer
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.
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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…
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Independent Study: Body Futurism by Toby Shorin (Essay)
16 maart 2026 · 34 min
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. Lees meer
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 februari 2026 · 2 uur 30 min
All links and transcript: dialectic.fm/cab Lees meer
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.
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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…
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39: Andrew Reed - Don't Flinch
11 februari 2026 · 2 uur
Full transcript and links: https://dialectic.fm/andrew-reed. Lees meer
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.
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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 …
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38: Molly Mielke McCarthy - The Art of Peopling
29 januari 2026 · 2 uur
Transcript and all links: dialectic.fm/mmm Lees meer
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.
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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile resear…
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37: Trevor McFedries - Creative People Should Be Rich
20 januari 2026 · 2 uur 19 min
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.
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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams build their best w… Lees meer -
36: C. Thi Nguyen - Measurement, Meaning, and Play
13 januari 2026 · 2 uur 22 min
Full episode transcript and all linked references available at https://dialectic.fm/c-thi-nguyen. Lees meer
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 ma… -
35: Brie Wolfson - Loving Attention & Ease in Craft
6 januari 2026 · 2 uur 32 min
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 … Lees meer -
34: Ryo Lu - It's All the Same Thing
18 december 2025 · 2 uur
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.
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Dialectic is now presented by Notion. I am now focused on Dialectic full-time, thanks to their … Lees meer -
33: TBPN (John Coogan & Jordi Hays) - Inside Tech's Water Cooler
17 november 2025 · 2 uur 23 min
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 Lees meer00:00: Opening Highlights
03:18: Intro & Background
06:08: Technology vs. Business and the Strategy behind TBPN
12:08: Building a Media Business when Distribution is not Scarce
22:26: Being Entrepreneurs and Talent
30:33: Avoiding Audience Capture
35:57: Why Advertising is a Good Model
44:04: Technology's Circular References and Borrowing Ideas from New Places
53:20: Narrow vs. Wide Appeal
59:44: X (Twitter)-First Content and Other Platforms
1:14:35: Making Content People Want to Share and Taking Yourself Seriously and Unseriously
1:20:28: Val…
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32: Chris Sacca - Drifting Back to Real
5 november 2025 · 2 uur 37 min
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: Lees meer(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 Langu…
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31: Gabe Whaley - Playing the Crowd & Outlasting the Hype
15 oktober 2025 · 2 uur 5 min
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 MS… Lees meer -
30: David Senra - The Clarity of Commitment
30 september 2025 · 2 uur 18 min
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: Lees meer(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 Ti…
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29: Billy Oppenheimer - Attuned to Clues
10 september 2025 · 2 uur 21 min
Billy Oppenheimer (Website, X) is a researcher and writer who works closely with Ryan Holiday and Rick Rubin, and publishes the “Six at 6” newsletter. Billy is also working on his first book, The Work is the Win.
We kick off by discussing one of my favorite new ideas: "looking for clues," a process and philosophy for creativity that Billy learned from Rick Rubin. He shares the story Rick told him when he learned and adopted this language, which is so representative of how Billy (and I!) research in our work.
From there, we talk about Billy's robust research process and how he has created an external brain of the ideas and patterns that inspire him rather than relying on memory. We also talk about the importance of time as a filter and a series of maxims that underpin his work and creativity. We discuss the importance of inputs over outputs and his big idea and book title, "The Work is the Win," as well many related ideas on success, complacency, compounding, standards, initiative, local maximums, and more. We finish with some lessons from Billy's favorite people.
This conversation is a field guide for making things, pushing through the messiness of progress, and attuning yourself to the richness of the world that often takes the shape of clues.
Full transcript and all links: https://dialectic.fm/billy-oppenheimer
Timestamps: Lees meer0:00 - Intro
1:20 - Looking for Clues with Rick Rubin
17:42 - Billy's Own Clue-Seeking
24:26 - Balancing Listening to the Market and Finding Unique Influences
31:17 - Memory, Notecards, and Billy's External Brain
37:13 - Making Notes for an Ignorant Stranger, or Leaving Clues for Your Future Self
45:09 - Lingering and Time as a Filter
52:51 - Billy's Book and Big Idea: "The Work is the Win"
1:00:07 - Be Great Regardless
1:04:31 - Following Up Even When Your Abilities and Standards Don't Match
1:10:10 - Fending Off the Wolf at the Door
1:15:55 - Unfolding and Planting Seeds
1:18:17 - Taking Initiative and Opening Doors: "He Who Hesi…
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28: Maxwell Meyer - Starships & Road Trips
3 september 2025 · 2 uur 19 min
Maxwell Meyer (X, Newsletter) is the founder and editor of Arena Magazine, an "American Propaganda" print and digital publication focused on technology, capitalism, and civilizational progress. Max also works with Joe Lonsdale at 8VC and is the proprietor of his Iowan farm, Henry Hills. He was previously the editor of the Stanford Review.
Our conversation is about ideas Max is most interested in across storytelling and media, American values, technology and progress, capitalism, writing and craft, and deep love for his country.
We start with critique, the media's tendency toward cliché, and defending the new while building trust with readers. Then we talk about American ideology: its radical founding myth, collective enterprise, and a nation of movers. Max makes a case that national character ought to be lived and formed bottom-up, and repeatedly argues that cultural pendulum swings are as old as time and we need not overreact to the swings of the day. He describes tech's brief abandonment of the rest of America and talks through how we might export Silicon Valley's outcome-oriented culture to government and other industries. Max argues that the foundation of capitalism is simple: "you can't kill your counterparty." We of course discuss Arena, magazines, writing, editing, and his ambitions there too.
Above all else, Max makes the case for America, big and small: the beautiful, always-changing, rarely-agreeing, perpetually striving amalgamation of souls that stretch from sea to shining sea.
You can subscribe to Arena here: https://arenamag.com/subscribe
Full transcript and all links: https://dialectic.fm/maxwell-meyer
Timestamps: Lees meer00:00: Intro
01:14: Elon, The Media, Cliché, American Collectivism, and Cultural Pendulum Swings
09:07: Media, Criticism, and Defending the New
17:49: American Ideology: The Declaration, Communal Enterprise, Americans as Movers
28:20: Patriotism
33:36: Learning from the Rest of the World
40:27: A Case for Progress
49:38: Tech's Sepa…
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27: Mackenzie Burnett - Accounting for the American Dream
28 augustus 2025 · 1 uur 49 min
Mackenzie Burnett (Website, X) is the co-founder and CEO of Ambrook, financial software for independent businesses starting with farms and ranches. We trace her arc from a policy-first upbringing (USDA household, Congressional internships, climate-security research at Stanford) to a building software for rural America.
We talk about why Mackenzie loves America and cares about agriculture, the challenges of aligning sustainability with business and government, and pragmatically building resilience. Mackenzie talks about the American Dream and why independent small businesses are the foundation of it in many ways.
Then we get into Ambrook’s product philosophy: why “all roads lead to accounting,” how multi-P&Ls and biological inventories make farms deceptively complex, and why understanding bookkeeping and money movement enables better decision making and understanding over the long run for big and small businesses.
We also talk through Mackenzie's broad ambition for Ambrook; her growth as a leader; brand, aesthetics, and environment; Ambrook's editorially independent research division, Offrange, and more. Mackenzie is one of the most quietly ambitious and focused people I've met, and yet under her impressive and serious exterior is a life and love for America and its people that is all heart.
Special thanks to Josh Kale for his help producing this episode.
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Full transcript and all links: https://dialectic.fm/mackenzie-burnett
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Timestamps Lees meer00:01:11 Intro
00:02:51: The American Heartland
00:05:21: Agriculture, Policy, and Government
00:12:29: The Challenges with Prioritizing Climate Risk: "Long Term and Abstract"
00:18:04: Pragmatic Environmentalism and Resilience that Drives Business
00:21:49: The American Dream
00:25:52: The Importance of Independent Small Businesses
00:28:58: Entrepreneurship on the Frontier: America's First Entrepreneurs and Ambrook's First Customers -- Farmers
00:36:28: Biological Factories: Why Farms are Complex Businesses
00:40:41…
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26: Cyan Banister - A Fool’s Dérive
20 augustus 2025 · 1 uur 59 min
Cyan Banister (Website, X, Substack) is an investor, artist, and co-founder and General Partner of Long Journey Ventures. Previously, Cyan spent four years at Founders Fund and has a legendary angel investing track record alongside her husband, Scott, including early rounds in SpaceX, Uber, and DeepMind. Lees meer
Cyan is as original as they come: she grew up on a Navajo reservation and was homeless by 15, with a series of unlikely serendipitous moments combined with optimism, agency, and love of capitalism taking her to a very different life than the one she grew up with. I focused this conversation not on Cyan's work, but her unique approach to living.
We begin with Cyan’s “church”: a weekly visit to see Bobby McFerrin and co. do live, jazz acapella in Berkeley, CA. We discuss how this space ties to presence, openness, and play, and then talk about the tension between novelty and consistency as she continues on her own path toward self-love and mindfulness. She also tells me about her radical approach to accountability and the empowering results of assuming that everything is her fault.
One of Cyan's favorite words is the French dérive, or an intentional drift, and it embodies her approach to the world. She moves with childlike wonder, seeking to see things and people from new perspectives and challenging others to react beyond their default settings. She daydreams about the outcomes she wants and has remarkable conviction and faith even when others do not believe her.
We wrap with a grab bag representative of Cyan's diverse interests, from filmmaking and performance art to the US Constitution to Bill Murray. Cyan manages to combine randomness and intentionality, naiveté and sober-minded awareness, humility and conviction. I hope you are are as inspired as I am to live more playfully, seriously, and courageously.
Full transcript is available at https://dialectic.fm/cyan-banister
Timestamps
0:01:23: Intro
0:03:45: Cyan's "Church"
0:16:21: Stillness, Mindfulness, an…
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25: Reggie James - Our Infinite Mirrors (Live at FWB Fest)
13 augustus 2025 · 58 min
Reggie James (Substack, X) is a designer, writer, and entrepreneur. Reggie previously founded Eternal and recently edited and published Hardware 2024, a book highlighting recent attempts at creating a different hardware future. This conversation happened live on stage at FWB Fest 2025 in Idyllwild, CA.
We explored Reggie's frame of technology as a mirror and the Kevin Kelly-inspired notion that technology has an agenda of its own. Reggie has a fresh perspective on brand and "feel" as they relate to technology products, why friction can create meaning, and a Naoto Fukasawa-influenced view that design is about communicating values. The latter, for Reggie, originates with writing.
We dipped into a discussion about how hardware and how it shapes our software cultures, and what a world with more basic luxuries like the iPhone might look like. We also discussed "loaded" technologies and the current narratives that are working in crypto vs. what might be idealized.
The conversation concludes with a zoomed out meditation on myth, American western idealism, personal history, and what type of vision is required to create something radically new. This episode is shorter than usual given the live nature, but it's jam packed and I'm thrilled that we were able to cover a lot of ground across many of the ideas that are representative of Reggie.
Full transcript and all links: https://dialectic.fm/reggie-james
Video version from FWB livestream available here.
Timestamps Lees meer3:05: Technology as Mirror
8:04: De-fanging Loaded Technologies
12:43: Writing's Role in the Design Process
16:13: Affordances, Software, Hardware, and Values
22:53: Universal Luxuries
25:46: Friction and How Technology Can Make us Feel
30:16: The Role Brand Plays in Technology Today
34:30: Successful Narratives in Crypto
41:30: Crypto as a Mirror
44:39: American Myth & West
47:56: Personal Myth
54:16: Vision
References
What Technology Wants - Kevin Kelly
Crying in the Garden ~ Closing Eternal - Reggi…
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24: Linus Lee - Engineering for Aliveness
4 augustus 2025 · 1 uur 50 min
Linus Lee (Website, X) is a builder, engineer, and writer who explores how software can amplify our abilities, humanity, and agency. He builds, researches, and advises on AI at Thrive Capital, a venture capital firm, and continues to write and hack on personal projects.
Previously, Linus held research or engineering roles at Notion, Betaworks, Replit, and others, and has built over 100 personal projects on the side--including his own programming language and most of the tools he uses day to day. Most of his work, writing, and projects revolve around language, knowledge work, thinking tools, machine intelligence, and latent space for creativity.
We begin with how technology can concentrate or distribute power and amplify our diminish our agency. Then he breaks down his framework around instrumental and engaged interfaces, why representation is so critical in tools, and talks through what 'tools for thought' actually means. We also discuss the state of LLM tools and how they can become more robust, as well as how latent space could be codified to help us understand more qualitative domains. This bleeds into his approach to and work at Thrive, which we discuss in detail.
Linus is attuned to the ways technology can make us more or less human, and that's reflected throughout. Technology is not determined: the future we imagine and create is entirely up to us. Will we optimize ourselves into something non-human, or dream our way into something beautiful?
Views expressed here are the interviewee's and not intended as investment advice. Lees meerFull transcript and all links are available at https://dialectic.fm/linus-lee
Timestamps:
(2:23): Values and Technology as an Amplifier for Agency
(9:57): Instrumental vs. Engaged Interfaces and Tools
(20:05): Representations, Abstraction, and Exposing Complexity
(33:23): Dreaming of Thinking Tools, Especially Beyond Text
(48:06): LLMs, Mechanical Thinking, and Going Beyond in How We Understand
(5…
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23: Tamara Winter - Tacit Trust & Caring Curiosity
28 juli 2025 · 2 uur 11 min
Tamara Winter (X) is the Commissioning Editor of Stripe Press, where she exercises her taste to identify the knowledge and "ideas for progress" that matter most in alignment with Stripe's mission: to increase the GDP of the internet.
"Tammy" worked at the Charter Cities Institute and the Mercatus Center at George Mason University, which is chaired by Tyler Cowen.
Tammy is obsessed with tacit knowledge and the illegible parts of the world that actually support so much of our lives, work, and societies. This includes taste, charisma, relationships, and a wide-range of load-bearing infrastructure that supports healthy and trustful societies, from small-talk and manners to hidden forces that prevent anti-social behavior and maintain safe places to live and work.
We discuss this and more, including how she selects the ideas worthy of Stripe's audience, her unique career path, her refreshing take on agency, her standards for herself, reading and writing, and how she chooses how to spend her time. Above all, Tammy's incredible love of other people shines throughout the conversation.
Full episode transcript with all linked references: https://dialectic.fm/tamara-winter Lees meerTimestamps
2:09: Taste, absorbtion, and influences
10:54: Deploying your taste
15:49: Ideas that matter and taking yourself seriously
22:13: Aesthetics
24:16: Choosing Teachers and Authors
28:15: Charisma & delightfullness privilege
34:59: Living a relational life
44:07: Trust, social scaffolding, and small talk
51:01: Erosion of social norms, low-trust environments, and load-bearing infrastructure
1:02:17: Cultural arson and the dark sides of "you can just do things"
1:15:44: The healthy kind of agency
1:20:45: Tammy's N-of-1 path and who she aspires to rhyme with
1:28:38: Red herrings of success and focusing on outcomes
1:32:22: Assortive everything
1:37:52: Personal and professional standards
1:43:06: Journaling, great writing, and audience
1:57:29: Reading & Biographies
Key Links:
The…
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22: Nadia Asparouhova - Ideas that Infect
3 juli 2025 · 2 uur 5 min
Nadia Asparouhova (Website, X, Substack) is a writer and researcher who has spent much of her career in service of the question: 'what's happening here?' across various parts of the internet.
Nadia recently published her newest book, Antimemetics: Why Some Ideas Resist Spreading. She explores why consequential ideas, unlike memes and supermemes, fail to spread. She also recounts the last several years of online public and private life and how we're all less naive than we were in previous eras of the internet. Critically, she suggests a path toward poking our heads out of group chats and silos to engage in publicly discussing or promoting the ideas that matter most.
Her first book, Working in Public: The Making and Maintenance of Open Source Software, was published by Stripe Press. Nadia also worked at Substack, Protocol Labs, and Github, and has written extensively on Silicon Valley Culture; the importance of ideas and institutions; consciousness, attention, and meditation; and more.
Nadia's self-described sweet spot is when people respond to her writing by saying,"I read this piece and it gave me words for a thing that I didn't know how to express before." I can attest that is true, both for Antimemetics and for much of her other thinking. And as much as she writes about ideas, I admire how focused she is on how they might produce action.
Nadia believes that important ideas infect us, and the reasonable response to that is to be tremendously thoughtful about our attention. I hope this conversation inspires you to put great care into where your attention goes. Lees meerTranscript and all links: https://dialectic.fm/nadia-asparouhova
Timestamps:
1:31: Why Ideas Matter
9:33: The Last 10 Years of the Internet and Attention Collapse
17:07: How The Internet Caused Attention Collapse
19:59: Private Coordination in Public Spaces
24:01: Legibility and Illegibility as a Tactic
28:28: Ideas Are Not Created Nor Discovered; They Infect Us
35:17: Defining Antimemes
42:00: Ideo…
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21: Geoffrey Litt: Software You Can Shape
19 juni 2025 · 2 uur 29 min
Geoffrey Litt (Website, X) is a designer, engineer, writer, and researcher at Ink & Switch, where he champions malleable software: the idea that ordinary people should be able to mold the digital tools they rely on every day.
Ink & Switch is an independent research lab focused on how computers can help us think and work. While researching and writing, Geoffrey and team also build products and prototypes to explore how their ideas can exist in practice. Geoffrey got his PhD at MIT CSAIL, where he built on his inspiration around computational media like spreadsheets, hoping to push more software toward the ethos of end-user programming, but without the technical complexity. In a sense, why should using software and changing it be any different? Previously, he built software for teachers at Panorama Education, which he joined out of school as one of the first employees.
Geoffrey and collaborators recently published a definitive piece on malleable software and we discussed it in detail. We dig into why most modern apps feel like sealed boxes rather than flexible tools and environments, and what changes when your app, document, or workspace, feels more like Lego than machinery. Geoffrey makes his case that we want software tooling to feel like a chef knife, not an avocado slicer, and we talk about how the best designed tools help users up a smooth slope of learning and ability. He argues in favor of deeper understanding, illustrated by one of my favorite ideas: The Nightmare Bicycle. We talk about how LLMs are enabling malleable software and how local tinkerers might be able to build systems for themselves and their team or communities that understand their needs more deeply than any professional designer could. Finally, Geoffrey lays out a call to arms for founders: build products that treat users as co-authors who understand their own needs, not just consumers.
On one level, this is a conversation about software and design. But it is really about agency. I hope it ins… Lees meer -
20: Yancey Strickler - Constellations of Creativity
12 juni 2025 · 1 uur 55 min
Yancey Strickler (Website, X, Metalabel) is a writer, entrepreneur, creative, and founder of Metalabel, a network and platform that allows creative people to release work together. He is also a board member, co-founder and former CEO of Kickstarter and is currently working on establishing a new kind of corporate structure, the Artist Corporation.
Yancey's life and work has revolved around what it means to be a creative individual, and how to improve the cultural and mechanical forms that enable artists and creatives.
We talk about how much of modern society is rooted in individualism, how that wasn't always the case, and how the internet is evolving our sense of self. We get into creativity, the term's surprisingly recent origins, and why Yancey believes the 21st will be the "Creative Century." Then, we go beyond the individual and discuss the deeply-rooted longing that all of us have to be a part of something bigger than ourselves. Yancey suggests that is not simply about being subsumed by a collective, but by maintaining our individual star while becoming part of larger constellations—like the labels that have empowered the distribution of ideas for centuries. Finally, we discuss the forms Yancey has or is helping to build and imagine a future where even more of the world creates professionally. Lees meerMay we all shine more brightly and find others who inspire us to make wonderful things.
Full transcript and all links available at https://dialectic.fm/yancey-strickler.
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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net worths of $1M-100M to create its 2024 Wealth Report. They asked about financial goals, spending habits, how much founders themselves, investment portfolio breakdowns, risk tolerance, estate planning and philanthropy, and more. Visit https://joinhampton.com/community to access the report.
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Timestamps1:41: Individualism, Identity, and the Internet
19:13: Creativ…
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19: Henrik Karlsson - Cultivating a Life that Fits
3 juni 2025 · 2 uur 45 min
Full transcript and all links: dialectic.fm/henrik-karlsson
Henrik Karlsson (Substack, X) is an independent writer focused on "writing a few good essays." Two of them are among my most consistently recommended: on designing your life and finding your wife (or husband).
Henrik's always written, but lived a winding path across software programming, music, poetry, biology, an art gallery, and other odd jobs. A few years ago, Henrik and Johanna picked up their life in Sweden to move to a small island farm in Denmark so they could homeschool their daughters. He now writes on Substack full-time and lives an unusual dual-life: one is remote and intimate; the other is connected and wide.
My favorite theme of his writing is self-cultivation: introspection and action, designing a life that fits you by experimenting, how to think and how to learn, embracing being wrong and seeing past your blindspots, and living in concert with past and future selves.
I also love his writing on relationships: how to find your life partner, why writing helps others see the inside of your head, how to use the internet as a serendipity machine for finding your people, teaching and parenting, and what its like to be around exceptional people who make your world bigger.
He also writes about education, self-organizing systems, AI, exceptional childhoods, and more. But I find the topic rarely matters—all of his writing expands me. What a gift. I hope you enjoy the conversation as much as I did. May we all embrace the burden of freedom—freedom to iteratively unfold into a life we never could have imagined. If you enjoy the episode, please consider supporting Henrik's writing, as he is fully reader-supported.
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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net worths of $1M-100M to create its 2024 Wealth Report. They asked about financial goals, spending habits, how much founders themselves, investment portfolio br… Lees meer -
18: Tom Morgan - Wisdom in the Woo
28 mei 2025 · 1 uur 42 min
Tom Morgan (X, Substack) is a "curiosity sherpa," writer, and podcaster who runs The Leading Edge, a community for leaders focused on personal transformation and authenticity.
I first encountered Tom and his ideas during his talk at Sohn on Iain McGilchrist, left vs. right brain, and curiosity. Tom writes about complexity, curiosity, and consciousness, and wades into the deep end of various topics that most of us would place in "woo," mystic, and spiritual territories. He spent most of his career on Wall Street and brings a scientifically-inclined, rationalist approach to researching and amplifying some of the most surprising modern and ancient ideas about the nature of humanity and the universe.
With this conversation, I aimed to create a primer on Tom's writing, approach, and the ideas he returns to most. We discuss following your energy, how curiosity is a guiding force, complexity and emergence, and why the world is overrated toward left-brain rationalism. We explore practical questions—How do you know your gifts? When should you pivot or persevere? What does real exploration look like when the world offers no safety nets? And then we wade into much stranger, or even heretical ideas—at least for a modern, intellectual, western audience—including the notion that consciousness is much vaster than what we've come to understand, and how we are just a small part of a much bigger whole.
I hope you enjoy the conversation and consider some ideas that are much more fringe than you're used to. I definitely left it with more questions than answers. And more than that, I hope you are inspired to attune yourself to your curiosity. Perhaps, you may even have the faith to follow that thread pulling you toward what appears today only to be a wall.
Episode transcript.
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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net works of $1M-100M to create its 2024 Wealth Report.
They asked about fina… Lees meer -
17: Alex Danco - Innovation Begins with Gifts
21 mei 2025 · 3 uur 9 min
Alex Danco (Website, X, Substack) is a writer and Product Director at Shopify. Alex rose to prominence while writing his Snippets newsletter while at VC firm Social Capital in 2015. He wrote prolifically—about markets and financial systems, venture capital, startups, cities, culture, the technology-driven shift to a world of abundance, to name a few topics—through 2020, when he joined Shopify. Since then, he's had his hands full with Shopify and young kids, but recently published a flurry of new pieces on his blog while on paternity leave.
This conversation starts with one of Alex's most insightful ideas: that a culture of gift-giving underpins technology, innovation, and creative work, and is the key to solving many of capitalism's coordination problems. We then talk about what businesses will look like in a world of abundance: AI agents, massive and accessible infrastructure, and where moats might actually lie. Alex shares why AI-enabled creativity may resemble musicians finding their sound and how and where we might find internet-native subcultures in 2025. Then he explains what "the medium is the message" actually means across different content formats and why audio continues to thrive. We wrap up with Alex's thoughts on the U.S and Canada as someone who identifies with both places and by taking a peek into some of the books that have most influenced his thinking.
I've read Alex for years and I've always been impressed by how generative he is. That comes through in this conversation and I hope you are inspired to—like Alex—be more curious, creative, and most importantly, generous. Lees meerTranscript and all links available at dialectic.fm/alex-danco.
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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more. Visit https://joinhampton.com/community to learn more and apply.
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Timesta… -
16: Anjan Katta - A Sunrise Over Computing
5 mei 2025 · 2 uur 37 min
Anjan Katta (X) is Founder and CEO of Daylight, a new type of computer company.
Having a conversation with Anjan is a bit like trying reign in a wild animal: his horsepower, wide-ranging philosophical interests, and unbelievable depth in the areas he cares about make him one of a kind. Fortunately, all of that energy is being channeled into his life's work, Daylight Computer Company. Daylight's mission is to build a computer that amplifies our humanity. That starts with Daylight's first product: The DC1, a tablet that combines the power and functionality of an iPad with the screen of a kindle. Anjan has been building Daylight for seven years across extensive research on screens and hardware, many near deaths, and mission-driven motivation.
Anjan sees computers as a "magical medium" that we're in relationship with, unlike other tools. Unfortunately, "optimization of the means, yet confusion of goals" has led the technology industry to building hardware and software that sits in what he calls a "messy medium." With devices that can do anything and everything, they often fail to empower us toward the vision Steve Jobs called the bicycle for the mind.
Throughout, Anjan and I discuss a philosophy toward life, career, design, and creating meaning that I hope will inspire you, whether you work on technology or not. May we all aim to get closer to ourselves and our humanity.
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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more.
Visit https://joinhampton.com/community to learn more and apply.
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Timestamps:
(0:04): Hampton Lees meer(1:57): Anjan Intro
(3:54): A Bicycle for the Mind and The Computer: Tool or Medium?
(13:15): The Core of the Computer as a Magical Medium: Relationship
(16:39): The Waterslide/fall of Agency and Humanity as Nature's Generalists
(27:35): What drove Anjan to Co…
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15: D.A. Wallach - Serendipity & Systems
28 april 2025 · 2 uur 33 min
D.A. Wallach (Website, X, Substack, Spotify) is an investor, musician, writer, and polymath. Today he co-runs Time BioVentures, backing frontier life-science and healthcare startups. Before that, he was an investor in in SpaceX, Spotify, Emulate, Beam Therapeutics, and Ripple, among others, and toured the globe as half of Chester French. He also released music as a solo artist and was Spotify’s first Artist-in-Residence.
Our conversation moves from engineered serendipity—the art of a well-aimed cold email & surfing the web—to complexity science, the Santa Fe Institute, and what better systems might look like. We dive into markets and medicine: investing with a creative mindset; timing in biotech including CRISPR and GLP-1s; and the tension between free-market innovation and healthcare as a human right. D.A. unpacks how incentives shape everything from venture bubbles to hospital billing and how LLMs might move us closer to a universal standard of care.
In the back half we talk creativity, beauty, art, and performance. We discuss whether AI makes us lazy or amplifies originality, DA's many lives across art, tech, and business, and end on his plea for artists to reclaim their throne of "cool". I hope you're inspired by D.A's combination of curiosity and depth and are reminded that you don't have to stay in one lane, regardless of how impressive it might be.
Full episode transcript and all linked references available here.
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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more. Visit https://joinhampton.com/community to learn more and apply.
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Timestamps: Lees meer(0:04) Hampton
(1:56) Intro to D.A.
(3:29) Curiosity, Serendipity, and the Power of Cold Emails
(9:21) Web Surfing & D.A.'s Potential One-Man Show
(13:28) Learning to Go Deep: Explore vs. Exploit
(19:18) Complexity Scienc…