Dialectic

Full transcript and all links and references: ⁠dialectic.fm/ian-rogers⁠.

Ian and I made a playlist with albums/songs mentioned here (Apple, Spotify).

Ian Rogers (X, LinkedIn) is Chief Human Agency Officer of Ledger, the Paris-based security company whose hardware wallets secure much of the world's crypto. He now focuses on how Ledger can enable us to work with AI agents while maintaining our secrets and value.

His career has spanned music, culture, brand, and "the technolog(ies) people are going to hate next." He built and ran the Beastie Boys web presence in the 90s before working on music on the internet for over a decade: file sharing Nullsoft (Gnutella and WinAmp), early streaming at Yahoo!, direct-to-fan commerce at Topspin, Beats Music, and finally Apple, as an abbreviated list. He then joined LVMH as its first Chief Digital Officer, working with Bernard Arnault and its many Maisons to bring them into the internet era. More recently, he joined Ledger to improve its product experience, including collaborating with Tony Fadell to create Ledger's flagship form factor, Ledger Stax.

Ian's roots are skateboarding and music, which formed alongside a punk rock ideology while growing up in Indiana in the 1980s. I am glad to have captured a long conversation that covers the many flavors of Ian, and the threads that have persisted through his many lives. That includes: individuality; being a participant, not a spectator; what makes a scene; building brands; trying to help Kanye; and why new culture is always being made—it's just that you have to find the 1% that's awesome. Also: ushering forward and translating frontier technologies; being pushed by Jimmy Iovine; why security matters in the AI era; why AIs aren't people; what he wants to automate; learning to fail; advice on relationships across work, parenting, and love; and a whole lot of love for music—from his 2026 pick Twisted Teens to his desert island albums to tea with Paul McCartney.

I hope you're inspired to participate in the world and make great things. Thanks to our friends at Ledger for hosting me.

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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

(1:37) Intro to Ian & Thanks to Notion

(5:22) Start: Tattoos, Individuality, and Punk Rock: Spectator vs Participant

(16:44) What Makes a Scene?

(25:24) New Culture, 99% of Everything is Garbage, Finding the 1%

(40:09) Niche, Quality, and The Blockbuster vs. The Snowball

(53:35) Brand, Selling Culture Before Product, and The Age of the Individual

(1:08:12) Aggression, Patience, and Being Pushed

(1:16:52) Translating New Technologies, Empowerment, and Agency

(1:25:19) Interfaces, Ledger, Security, and Ideology

(1:39:56) Ian's New Role: Chief Human Agency Officer

(2:06:03) Seeing What is Real, Comfort Being Wrong, Chasing What's Fun and Cool

(2:13:45) Lessons from Skateboarding and Favorite Albums

(2:22:56) Working with Your Friends, Parenting, Love, and Remembering to Stay a Participant

(2:35:47) Thanks Again to Notion

Zhengdong Wang (Website, X, LinkedIn) is an AI researcher based in London.

He writes annual letters (inspired by Dan Wang), mainly about AI progress, and his 2025 letter blew me away and inspired me to meet him. In it, he describes his ‘compute theory of everything,’ and makes the case that it would be stranger if AI progress slowed down than if it continued. Put a different way, reading his letter helped me get closer to truly feeling the wave of AI progress.

It took Zhengdong a long time to become “AGI-pilled,” despite years of feeling like he was late to AI and working as a research engineer for the last five. I talked to him about what it will take for the rest of us to see what he sees, and feel what he feels. We also discuss why AGI may be a hazier target than simply seeing AI progress as “the model does the eval,” and why recursive self-improvement may be both happening and less fantastical than it may seem. ZD makes the case that based on the rate of progress and scaling, skeptics will simply be proven right or wrong soon. We talk a bit through what narrative and political challenges the AI industry faces ahead of this transition.

Then there are the implications of all of this—namely how AI progress accelerates the question of what we each value, how we will spend our time, and where we will find or create meaning. ZD takes a stab at some of those impossible questions and shares some other favorite miscellanea that is reflective of the range of his letters.

I hope this conversation helps you feel the wave a bit yourself, and that you remember that, regardless of how much change lies ahead, we still get to make our meaning. We get to choose.

Full transcript and all links: dialectic.fm/zhengdong

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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 to Notion

(4:33) Start: Why Research: "I Just Want to Know"

(12:25) The Model Does the Eval: AGI as a Moving Target, RSI, and Laser Beams

(33:17) The Compute Theory of Everything and Feeling the Wave

(53:17) The Myths AI Needs, Competition vs. Power Concentration, and Whether Progress Is Inevitable

(1:13:42) "Who Could Possibly Compete?": Post-AGI Meaning, Work, and Questing

(1:29:28) Are You Having Fun? Vacations, Mattering, and How to Live

(1:47:13) Annual Letters, Economist Obituaries, London, and Burke

(2:06:33) Closing & Thanks to Notion

Full transcript and all links: ⁠dialectic.fm/jack-conte⁠

Jack Conte (Patreon, YouTube, YouTube Pt2, X, LinkedIn) is the co-founder and CEO of Patreon. He is also a lifelong artist and musician, who at his peak released 100 music videos per year between his bands Pomplamoose (a duo with wife Nataly Dawn) and Scary Pockets (a funk collective), and was a longtime YouTuber.

Jack is not a tech CEO who happens to like music. He is an obsessive, prolific artist whose first conventional job is running Patreon. This has shaped him as a founder and executive, and his mission at Patreon is to build an enduring and truly creator-first company that empowers creators to earn a living from their work.

We began with how he manages to do it all, where his energy comes from, and what it’s like to be “post-chaos.” Then, we talked about art, content, and commerce, Patreon’s model (that isn’t actually pure patronage), and why Silicon Valley undervalues art, brand, and narrative — and Patreon. Jack shared the benefits of a business model that is fully aligned with creators, why he hates the word influencer, and why he’s still the right man for the job after 13 years of leading Patreon. We also covered what great leadership looks like, building fans and community, filmmaking, authenticity (from Charlie Kaufman to Prince), and remembering to take risks until the very end.

I hope you’re inspired to make things you are proud of and to draw the next page even when you have no business doing so.

While I have you: I’d strongly recommend Jack’s recent SXSW talk on AI, creativity, and change.

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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 Becoming Post-Chaos

(22:04) Combining Creativity and Business and Art vs. Content

(33:21) Advertising vs. Membership & Patronage vs. Patreon

(44:06) Jack's First and Only Job, and Silicon Valley's Undervaluing of Creativity, Brand, and Storytelling (and Patreon)

(55:17) Building for Creators First, Incentive Alignment, Trust, 100 Years of Patreon, and Why Jack is the Right CEO for Now

(1:04:49) Leadership: Types of Ambition, Obsession, Self Reflection, Bias to Action, Learning from Others

(1:12:59) Talent vs. Enthusiasm, Being Proud of What You Make, Making Fans and Being True, Managing Parasociality, and Community

(1:28:30) Filmmaking, Labels and Collectives vs Individuals, Breaking Patterns, Creative Intimacy, Music, Patreon's Origin, Persistence, Lucid Dreaming, and Taking Risks

(1:49:26) Thanks Again to Notion

Nan Ransohoff (X, Substack, Website) is Head of Public Goods and former Head of Climate at Stripe. This includes Frontier (which she co-founded): an advance market commitment that accelerates carbon removal by guaranteeing demand for it before it exists. They also recently launched Intercept Fund, a new effort to end respiratory infections, led by Nan and Charlie Petty.

Nan has written extensively about Stripe’s efforts and philanthropy broadly, including her call for general managers for the world’s pressing problems, and on what she calls the third wave of American philanthropy.

We talk about what a "Nan" is and why we need GM’s: ambitious founder-like people who obsess over an outcome and work backwards from it, wearing whatever hat the problem requires. We discuss taste in big problems, slicing them up and making them tractable, and why vision is in short supply. We also discuss the coming wave of new philanthropic dollars (est. ~$40B/year), primarily driven by The OpenAI Foundation, Anthropic Founders, and Anthropic employee matching, and how the ecosystem will need to mature to effectively deploy this much capital. Nan also reflects on her unlikely turn toward philanthropy and what it felt like to get off the ladder of a specific kind of ambition. We wrap up with a range of miscellanea and some fun debates. I hope you are inspired to notice problems you can’t ignore, be optimistic and specific about the world you hope for, and choose an (unlikely) path that you are proud of.

Transcript and all links: https://dialectic.fm/nan

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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, and Working Backwards from Outcomes

(18:55) Good Taste in Problems, Vision, and Good Finish Lines

(35:43) Advance Market Commitments Tactically Solving Carbon Removal

(41:35) Focus and Sketching Out or Slicing Up Messy Problems

(49:39) Legibility, Public Rallying, and Ambition in Philanthropy

(54:38) Third Wave Philanthropy and Hard to Quantify Problems

(1:06:50) Risk Tolerance in Philanthropy and Scarcity of Funders and Allocators

(1:15:22) The $40B Tidal Wave of New AI-Money and Why Start Now

(1:19:53) Amount of Capital, Government Philanthropy, and Making Philanthropic Founders Rich

(1:31:44) Nan's Mid-Career Inflection Point and Getting Off the Obvious Path

(1:39:47) Grab-bag: Why Stripe Funds Public Goods, Making Things with Friends, Creative Partnership, Iceland Drone, and Scone Heads

(1:49:39) Syllabi for the Squishy Topics & Study vs. Experience

(1:57:01) Inputs & Outputs and GLPs for Attention

(2:04:38) Closing: Interviewing Parents and Imagining an Obituary

(2:09:58) Thanks Again to Notion

Tyler Cowen (Website, X, Marginal Revolution, Conversations with Tyler) is an economist at George Mason University, leads the Mercatus Center, and is the author of many books including The Great Stagnation and Average Is Over. He has blogged nearly daily at Marginal Revolution for over 20 years, has interviewed hundreds of world-experts on Conversations with Tyler, and runs Emergent Ventures, a prolific grants program that has funded multiple Dialectic guests.

Nabeel S. Qureshi (Website, X, Substack) is an entrepreneur, writer, and researcher. He runs a stealth startup. Previously, he was a Visiting Scholar at Mercatus and spent nearly eight years at Palantir. He writes some of my favorite essays, including "What Makes Art Great" and "Rented Virtue", and was previously a guest on Dialectic for episode 13: "The Will to Care."

Tyler and Nabeel are good friends, and given how prolific Tyler is, I decided to use Nabeel as an entry point and interview them together. We discuss sacred commitments, AI acceleration, mentorship, friendship, and more, but I focused the majority of the conversation on art and aesthetics. Tyler and Nabeel are unlikely aesthetes given their day jobs, but in fact take art deeply seriously. They have a shared love for and similar tastes in art, music, and film, in particular. We discuss strange and beautiful art, aesthetic stagnation, and a wide range of favorites: The Beatles, Mozart, Mondrian, Springsteen, Lana Del Rey, Kanye West, Cassavetes, The Sopranos, Apichatpong Weerasethakul, and more.

Please enjoy, and thank you for supporting, listening, and watching through fifty episodes of Dialectic. I can't wait for the next fifty!

Transcript and all links: dialectic.fm/tyler-nabeel

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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:

(0:00) Opening Highlights

(1:18) Intro to Tyler & Nabeel

(3:02) Thanks to Notion

(4:38) Start: Sacred Commitments, AI, Markets, and Acceleration

(20:23) How Art Moves Us

(27:08) "Beauty," Strangeness, Great Art, Music, and The Beatles

(44:09) Film, Critics, Learning to Appreciate Depth, More Music, "Lowbrow" Art

(1:02:25) New Aesthetics, Sources of Inspiration, Optimism & Pessimism

(1:11:22) The Internet & Twitter's Virtue, Group Chats, and Cities

(1:21:35) Mentors, (Possibly Quitting) Writing Books, Friendship

(1:34:54) Interviewing, Identifying Talent, and Agency

(1:47:21) Closing Questions

(1:53:38) Thanks Again to Notion