Dialectic
Dialectic is a podcast that features conversational portraits of original people across technology, media, business, and creativity. Hosted by Jackson Dahl, each episode delves into the stories and insights of interesting individuals. The show aims to capture the unique perspectives and experiences of its guests.
Episodes
48: Henri Stern - Principled Enough to Be Pragmatic
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
47: Paul Scherer - A Friend That Brings Us Closer
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
46: Nicole Seah (Nix) - Loving What is Real
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
45: Nicholas Thompson - A Life of Long Form
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 earl
44: Jared Weinstein - Within Earshot, Out of Camera Shot
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,
43: Mario Gabriele - Reality is Story-Shaped
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
42: Celine Nguyen - Nurturing Your Mind in Public
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
41: Henrik Karlsson: Strolling Through Life's Labrynths
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
Independent Study: Body Futurism by Toby Shorin (Essay)
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.
40: Charles Broskoski - Everything is Personal
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 bega
39: Andrew Reed - Don't Flinch
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
38: Molly Mielke McCarthy - The Art of Peopling
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 F
37: Trevor McFedries - Creative People Should Be Rich
All linked references & transcript available at dialectic.fm/trevor-mcfedries.
Trevor McFedries (X, Instagram, Wikipedia) is a musician, technologist, and entrepreneur. Today he is the founder of Runner and 1/2 of electronic dance duo SoFTT. Previously, Trevor was co-founder and CEO of Brud, the company behind Lil Miquela that was acquired by Dapper Labs; Founder of FWB (Friends with Benefits); ea
36: C. Thi Nguyen - Measurement, Meaning, and Play
Full episode transcript and all linked references available at https://dialectic.fm/c-thi-nguyen.
C. Thi Nguyen (Website, Philpeople.org, X) is a professor of philosophy at the University of Utah focused on values, games, agency, art, aesthetics, and data. His new book, The Score: How to Stop Playing Somebody Else's Game is out now.
Thi is also the author of Games: Agency as Art, in which he expl
35: Brie Wolfson - Loving Attention & Ease in Craft
Full transcript and all links: https://dialectic.fm/brie-wolfson
Brie Wolfson (X) is a marketer, writer, storyteller, and curator. She’s Chief Marketing Officer of Positive Sum & Colossus, where she works closely with CEO Patrick O’Shaughnessy across investing and media and spearheaded Colossus Review, their new print publication known for superb long form profiles.
Brie also recently joined AI-
34: Ryo Lu - It's All the Same Thing
All links and transcript at dialectic.fm/ryo-lu
Ryo Lu (Website, X) is the head of Design at Cursor. Prior, he was a designer at Notion, Stripe, and Asana, working on some of the most influential software tools of the last decade. He is now focused on building the next generation of tools for making software.
Our conversation is an extensive exploration of Ryo's design philosophy, which is anchore
33: TBPN (John Coogan & Jordi Hays) - Inside Tech's Water Cooler
John Coogan & Jordi Hays are the hosts of TBPN (X, YouTube, Spotify, Substack), a daily live show covering the technology business. TBPN was launched only about a year ago, but has become a mainstay in tech culture and a center of gravity forterminally online technologists.
John was previously an EIR at Founders Fund and tech YouTuber. He co-founded Lucy Nicotine and Soylent. Jordi has co-founded
32: Chris Sacca - Drifting Back to Real
Chris Sacca is an investor and founder of Lowercarbon Capital and Lowercase Capital.
Prior to becoming an investor, Chris grew up in Buffalo, NY; studied around the world by way of the Georgetown School of Foreign Service; turned his student loans in $12M in the tech bubble of 2000 before losing it all and then some; and broke into Silicon Valley before eventually landing at Google, where he won
31: Gabe Whaley - Playing the Crowd & Outlasting the Hype
Gabe Whaley is co-founder and CEO of MSCHF (Instagram, Wikipedia), the art collective, fashion and footwear brand, startup, and fill-in-the-blank, famous for its viral products and cultural interventions.
A few notable works include Jesus Shoes (Nike Air Max filled with holy water), Severed Spots (a "decentralized" Damien Hirst print), Museum of Forgeries (One original Warhol and 999 perfect forg
30: David Senra - The Clarity of Commitment
David Senra (Website, X) is a podcaster and loves that title more than anyone. He hosts Founders, where he teaches the lessons of history's greatest entrepreneurs by way of the biographies he reads of them. This week, he launched a second show, David Senra, where he talks to the greatest living entrepreneurs (often about the lessons from Founders). The first episode with Spotify Founder & CEO Dani
29: Billy Oppenheimer - Attuned to Clues
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
28: Maxwell Meyer - Starships & Road Trips
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 a
27: Mackenzie Burnett - Accounting for the American Dream
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 cha
26: Cyan Banister - A Fool’s Dérive
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.
Cyan is as original as they come: she grew up on a Navajo reservation and was homeless by 15,
25: Reggie James - Our Infinite Mirrors (Live at FWB Fest)
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 te
24: Linus Lee - Engineering for Aliveness
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 bu
23: Tamara Winter - Tacit Trust & Caring Curiosity
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 know
22: Nadia Asparouhova - Ideas that Infect
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 y
21: Geoffrey Litt: Software You Can Shape
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 pro
20: Yancey Strickler - Constellations of Creativity
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
19: Henrik Karlsson - Cultivating a Life that Fits
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 o
18: Tom Morgan - Wisdom in the Woo
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
17: Alex Danco - Innovation Begins with Gifts
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. Sin
16: Anjan Katta - A Sunrise Over Computing
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 mi
15: D.A. Wallach - Serendipity & Systems
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 fi
14: Alex Zhang - Curating Cultural Playgrounds
Alex Zhang (Website, X, Instagram) is a cultural curator, community builder, and creative director. Currently, he's Chief Creative Officer of Powder Mountain, a where he's working with Reed Hastings to create a globally unique ski experience that combines art, architecture, and lots of fresh tracks.
Alex loves people and curating spaces and experiences for them: whether that means parties, music f
13: Nabeel S. Qureshi - The Will to Care
Nabeel S. Qureshi (Website, X, Substack) is a writer, entrepreneur, and former Palantir product lead known for his writing on technology, AI, Palantir, culture, and learning. After a brief hiatus writing and researching and spending nearly a decade at Palantir working across government, healthcare, and intelligence, he's now founding a new company.
The first half of the conversation focuses on two
12: Che-Wei Wang & Taylor Levy (CW&T) - Iterating Together with Time
Che-Wei Wang and Taylor Levy are the founders of CW&T (Website, Instagram, X, TikTok), a Brooklyn-based studio creating products that exist somewhere between art, design, and engineering.
The husband-and-wife team met at NYU ITP and shares a background across industrial design, architecture, computer science, film, including time at Pratt Institute and MIT. They won the 2022 Cooper Hewitt National
11: Eugene Wei - Amusing Each Other to Death
Eugene Wei (Website, X) is a writer, product thinker, and cultural observer best known for his essays on technology, media, and social networks, including Status as a Service, Invisible asymptotes, and TikTok and the Sorting Hat.
Eugene spent seven years at Amazon in its early days before following a brief detour to pursue filmmaking at UCLA. He then led product, design, editorial, and marketing t
10: Josh Wolfe - Illuminating Tomorrow
Josh Wolfe (Website, X) is co-founder and Managing Partner of Lux Capital, a venture firm focused on emerging science and technology at the outermost edges of what is possible.
Josh is a masterful storyteller who moves seamlessly between science, culture, and markets. As an investor, he seeks the counter-narrative—what others aren't talking about—and has backed countless breakthrough companies in
9: Jacob Horne - Markets for What Matters
Jacob Horne (Website, Zora, X, Farcaster), is co-founder and CEO of Zora, a platform that allows the tokenization of media.
Jacob started his career at Coinbase where he was a product lead and helped create USDC. Five years ago, he left to wade deeper into the waters of internet and crypto-native coordination and creativity and co-founded Zora.
His central interest is how people coordinate togethe
8: Steph Ango - Tools for Amplifying Our Light
Steph Ango aka Kepano (Website, X) is a designer, writer, entrepreneur,and toolmaker, best known as the CEO of Obsidian, a powerful and flexible writing and thinking tool.
Steph's education is in biology and industrial design, but he is true multi-hyphenate creative, working across mediums including software, hardware, supply chain and packaging, words, wood, furniture, ink, color schemes, open-s
7: Toby Shorin - The Shapes of Culture
Toby Shorin (Website, Blog, X) is a researcher, writer, consultant, and cultural anthropologist for the internet era.
His interests and work include culture, identity, organizational design, psychology, cryptocurrency and blockchains, brands, health and care, spirituality, and social forms and institutions. Today, Toby works on Care Culture, a community and research platform focused on mental hea
6: Chris Paik - Intentionally in Search of the New
Chris Paik is a General Partner and Co-founder of Pace Capital, a Venture Capital firm in New York City.
He invests in technology and internet businesses at Pace, and previously did the same at Thrive Capital, which he joined in the earliest days. At Thrive, Chris invested in Twitch, Unity, Patreon, among others. Chris is a profoundly deep thinker who relies on behavioral economics to build robu
5: Tina He - Internet Citizen and Philosopher in Action
Tina He (Site, X, Newsletter) is a product designer, entrepreneur, writer, and amateur philosopher. She is a product lead at Coinbase, where she works on developer tools for its network Base. She joined Coinbase through the acquisition of her company, Station Labs.
Tina grew up in China before moving the U.S. at age 14. As an adult, Tina has been a dual-citizen of New York City and the internet.
4: Ava - Alive in Writing and in Love
Ava (X) is one of my favorite writers. She writes full-time for her Substack, Bookbear Express, and focuses on love, friendship, emotions, culture, and psychology.
I'm not sure there's anyone I've more consistently recommended to friends and loved ones in recent years, and it seems like the world agrees: Ava now has over 30,000 subscribers. One of my favorite parts of this episode was reading ex
3: Dan Romero - Why Information Should Flow on Protocols
Dan Romero (Farcaster, X, Website) is the CEO and co-founder of Farcaster, an open Twitter/X-like social network protocol built on blockchain rails.
Before co-founding Farcaster in 2020, Dan previously worked at Coinbase as a Vice President, among many other roles. He joined the company as the 20th employee in 2014 and left in 2019. He's thought about and used Twitter-like networks for nearly two
2: Michael Dempsey - The Craft of Investing in the Future
Michael Dempsey (Website, X) is an investor, writer, technologist, and Managing Partner of Compound, an early-stage, thesis-driven, research-centric investment firm.
Michael and Compound invest in seed and pre-seed science and technology companies in categories like healthcare and biotech, machine learning and AI, robotics, and crypto. He writes prolifically across a range of topics and I've alwa
1: Jason Liu - The Freedom in Being Nobody
Jason Liu (Website, X, Github, Newsletter) is a technologist, consultant, teacher, and friend.
He spent the first part of his career as a machine learning engineer, mostly at Stitchfix, only to run into a wall: a hand injury that prevented him from being able to write any software for over a year. Fortunately, he's not so one-dimensional, and spent time reclaiming somatic experience in learning
Recommended
#100MasterCoaches with Mel Leow, MCC
100% Mixtape Podcast
100 With The Hunter's
10-41: A UCSO Podcast
108.3 WGKSRADIO DEEP HOUSE PARTY
10 at a Time
10Fold Founders
10% Happier with Dan Harris
10-Minute Contrarian
10 Minutes Korean - Learn Korean & English Naturally
10 Minutes with Jesus
10 Minute Teacher Podcast with Cool Cat Teacher
