Dialectic

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

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.

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, and Resisting Summary

(1:35:35) Literary Inspirations, Favorite Essays, Writing vs. Thinking, and Getting Better

(1:51:09) Writing to Publish, Authenticity, and Art

(2:00:38) Grab Bag: China, Silicon Valley's Virtues and Problems, AI Transition, The Relational Economy, Parties, Debates, Self Belief, and More

(2:35:16) Thanks Again to Notion

Select Articles From Jasmine


Silicon Valley is Bracing for a Permanent Underclass (NYT)


‘Chinese Peptides’ Are the Latest Biohacking Trend in the Tech World (NYT)


Claude code psychosis (Substack)


Notes on AI, labor, and China (Substack)


America against china against america (Substack)


The Human Skill That Eludes AI (The Atlantic)

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 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, Startups, and Crypto

23:39 - Why Digital Privacy Matters: Self-Determination, Security, and Identity

41:52 - Embedded Wallets, the Pivot, and Privy's Core Bet

55:18 - Reinventing Around Stablecoins Without Abandoning Crypto-Natives

1:06:42 - Joining Stripe, Privy Today, and What Stripe Is Becoming

1:22:54 - Crypto's Future, Power Laws, Optimism and Pessimism

1:38:14 - Closing: Asta, Stripe's Leaders, Being French, and Never Compromising

1:52:48 - Thanks Again to Notion