Dialectic

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.

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.

Henri Stern ( X , LinkedIn ) is the co-founder and CEO of Privy . Privy builds wallet infrastructure for developers, enabling them to let their users hold and use crypto, including stablecoins. Privy was acquired by Stripe in 2025 , and remain an independent organization within the company. They work with large fintechs like Ramp and Klarna while also supporting some of the most notable crypto-native platforms like Hyperliquid. Henri also supports a number of other crypto efforts within Stripe. Henri is thoughtful, measured, and principled. Yet he is also pragmatic. He doesn’t like to play phi

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

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 —

Full episode transcript and all linked references available at https://dialectic.fm/c-thi-nguyen.C. Thi Nguyen (Website, Philpeople.org, X) is a professor of philosophy at the University of Utah focused on values, games, agency, art, aesthetics, and data. His new book, The Score: How to Stop Playing Somebody Else's Game is out now.Thi is also the author of Games: Agency as Art, in which he explores how game designers work in the medium of agency, but sculpting a players abilities, goals, and obstacles to create "harmonious action." I first learned about Thi's work via his interview with Ezra K

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

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 ins

Jared Weinstein (LinkedIn, X) is an investor, advisor, civic leader, and founder of Overton. This is his first interview. Full transcript and all links at dialectic.fm/jared-weinstein. Jared spent his twenties in the George W. Bush White House, starting as a scheduling intern and rising to become the President's personal aide. He went on to Stanford GSB, consulted for Palantir in its early days, and was a founding partner of Thrive Capital in NYC, helping build it into one of the most respected venture firms in the world over eleven years. After leaving Thrive in 2022, Jared returned to Birmin

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 li

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 defe

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 inclu

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 exte

All links and transcript at dialectic.fm/ryo-luRyo 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 co

Transcript and all links: dialectic.fm/mmm Molly Mielke McCarthy (Website, X, Substack) is an investor, writer, and founder of Moth Fund, an early-stage fund focused on backing "moths": quirky, quiet, mission-driven founders who are often underpriced by traditional venture capital. Molly's career has been a dance between "peopling" and making. She's held design, product, and editorial roles at Figma, Notion, Stripe Press, and The Browser Company, and explored film, photography, and the arts before finding her way to venture, where she started as a scout for Sequoia Capital. Today, she invests

All links and transcript: dialectic.fm/cab Are.na channel for this episode: are.na/jackson-dahl/dialectic-cab Charles Broskoski (Website, Are.na, X), aka Cab, is an artist turned entrepreneur and co-founder & CEO of Are.na, a platform for collecting, connecting, and self-directed learning. I created an are.na channel for all of the references I used in preparation for this episode. Charles began as an artist before becoming a software engineer, and started Are.na with many collaborators out of a desire to replace the now defunct del.icio.us after it was acquired by Yahoo. He and a range of col

Full transcript and links: https://dialectic.fm/andrew-reed. Andrew Reed (X, Website, Sequoia) is a growth investor at Sequoia Capital, where he has invested in companies including Robinhood, Figma, Klarna, Phantom, Vanta, and ElevenLabs. He is quietly one of the best growth investors of his generation. We begin with how Andrew's competitiveness and humanity coexist—the twin brother rivalry, the football player who also did musicals, the Goldman analyst who came to value people over spreadsheets. He also shares how an early lack of confidence helped him become a great observer of people and si

Transcript and all linked references: https://dialectic.fm/henrik-2 Henrik Karlsson (Substack, X) is a writer and essayist. His newsletter, Escaping Flatland, explores attention, agency, relationships, and the inner life of making things. He is one of my favorite essayists, and I spoke to him previously on Dialectic 19: Cultivating a Life that Fits in Spring 2025. We met again in Copenhagen, this time on video. Our first conversation focused on designing your life iteratively and relationships. This time is about the messiness of creativity and problem-solving. We circle a central theme of nav

All links and transcript available at dialectic.fm/celine-nguyen Celine Nguyen (Website, Substack, X) is a writer, software designer at Watershed, and literary critic. She writes personal canon, a newsletter about literature, design, art, and technology that has grown to tens of thousands of subscribers. She has also written for The Atlantic, Asterisk Magazine, and more. I discovered Celine with her reflection on two years of writing her newsletter, where she made the case for living a life of the mind, reading great things, and writing online: "After 2 years, I’m convinced that reading and wr

All links and transcript at dialectic.fm/mario-gabriele Mario Gabriele (X) is a writer, investor, and analyst. He is founder of The Generalist and Partner at Hummingbird. He aims to bring the rigor of investment analysis with writing quality and style that is closer to the New Yorker. His profiles, deep dives, and briefings are amongst the highest quality writing in the technology business, and he interviews practitioners weekly on his podcast. Recently, he wrote the definitive (and nearly book-length) piece on Peter Thiel’s legendary investment outfit, Founders Fund, and profiled Microsoft’s

A new experiment: I thought it would be fun to share audio versions of essays or writing from past or future Dialectic guests. Toby Shorin (ep. 7: The Shapes of Culture) recently published 'Body Futurism,' a piece based on a talk I heard him give in 2024 and that I loved. You can read this piece at https://writing.tobyshorin.com/body-futurism/. It is provocative and feels increasingly prescient. Toby suggests that we must return to the body—and not just bodies in theory but quite literally your, my, our physical bodies, as the starting point for how we think about what is good for how we live

Paul Scherer (X, LinkedIn) is the founder of Eigen (check out their beautiful website), where he’s building a mutual friend: an AI that brings people closer together and helps us belong. Paul grew up in a small town outside of Frankfurt, Germany, and dropped out of high school at seventeen to work on startups, including Augment. He recently raised $15M from Benchmark, with legendary partner Peter Fenton comparing him to the founders of Facebook, Twitter, Instagram, and Snapchat. I was introduced to him by Notion co-founder Akshay Kothari, who is an angel investor in Eigen. Dialectic guest Brie

Nicholas Thompson (Website, X, LinkedIn, Wikipedia) is the CEO of The Atlantic, an elite distance runner, and the author of The Running Ground—a memoir about his father, his life, and the sport of running. Full transcript and all links at dialectic.fm/nick-thompson. Nick has led The Atlantic to tremendous subscriber growth and profitability since joining the then-money losing publication in early 2021. He was previously editor-in-chief of WIRED and editor of newyorker.com. He also co-founded The Atavist, wrote The Hawk and The Dove, and is a prolific interviewer, including his latest series,

Nicole Seah (X, Substack, LinkedIn), aka Nix, is a writer at Starting From Nix and investor at Costanoa Ventures. She recently launched New Ontologies, where she profiles founders and companies thinking ambitiously about the future. Her first piece is live now, on Ando: the team building a chat platform for the era of agents. Nicole balances identities with poise, moving between the literary and the practical. I spoke to her about different kinds of beauty and how it takes us out of ourselves, Nietzsche’s case for tolerating strangeness, and choosing reality over fantasy. Then we discuss duali