Inside Substack’s $650M Playbook for the Future of Media

In a world where attention is fragmented and algorithms rule the content landscape, Chris Best and Hamish McKenzie are taking a radically different approach with Substack. Rather than chasing clicks, Substack focuses on a simple yet powerful idea: creators should own their work and make money directly from their audience through paid subscriptions. With over 5 million paid subscriptions and tens of millions of active readers, Substack has turned this model into a transformative force in media. In this episode, Chris and Hamish unpack how they’re reshaping creator economics, navigating AI’s role in creativity, and enabling a new era for writers, from serialized fiction to short-form video. Their bet? That if content adds real value—whether it educates, entertains, or helps people earn—audiences will pay for it. In our conversation, we explore: • How Substack grew from a simple newsletter tool to a multi-format media platform with 5 million+ paid subscriptions • Why the "soul connection" between creators and audiences is becoming more valuable in an AI-dominated world • The inside story of Substack's clash with Elon Musk and how it ultimately strengthened their platform • Why the ceiling for great writing and culture might be much higher than we're currently imagining • How Substack's subscription model creates dramatically better economics for creators than ad-supported platforms • Chris's "grand unified theory" for how AI will influence content creation and consumption • Why their short-form content isn't just a "sticky trick" but a pathway to deeper engagement and discovery • The future of traditional prestige media brands • Much more Thank you to the partners who make this possible Vanta: Automate compliance and simplify security: https://www.vanta.com/mario Brex: The banking solution for startups: https://www.brex.com/mario WorkOS: The modern identity platform for B2B SaaS: https://workos.com For a full transcript of the episode, please visit: https://thegeneralist.substack.com/p/... Timestamps (00:00) Intro (05:27) An overview of Substack and its current scale (06:53) The origin story of Substack (19:20) Finding the first believers (24:17) Successful fiction on Substack, and why there’s potential for much more (29:09) The different mediums available on Substack (32:27) How Substack’s feed differs from social media (37:33) The clash with Elon Musk and Twitter/X (47:23) How Substack’s network helps creators succeed (52:07) TikTok creators moving to Substack after the ban (56:20) The future of paid media consumption (58:24) Chris's grand unified theory of AI and media (1:07:07) Substack’s AI tools (1:10:54) Why it’s hard to predict where AI is taking us next (1:13:42) Advice for traditional media institutions (1:16:48) Final meditations Follow Chris Best X: https://x.com/cjgbest LinkedIn:  / cjgbest   Follow Hamish McKenzie X: https://x.com/hamishmckenzie LinkedIn:   / hamishmckenzie   Resources and episode mentions —Books— • The Anxious Generation: How the Great Rewiring of Childhood Is Causing an Epidemic of Mental Illness: https://www.amazon.com/Anxious-Genera... • The Canterbury Tales: https://www.amazon.com/Canterbury-Tal... —People— • Jairaj Sethi on LinkedIn:   / jairaj-sethi   • Andrew Chen on LinkedIn:   / andrewchen   • Mike Kerns on LinkedIn:   / mike-kerns-63219   • Patrick Collison on LinkedIn:   / patrickcollison   —Other resources— • Substack: https://substack.com/ • Kik: https://kik.com/ • Listicle: https://en.wikipedia.org/wiki/Listicle • The dress: https://en.wikipedia.org/wiki/The_dress • Craigslist: https://www.craigslist.org/ • Stratechery: https://stratechery.com/ • The Weekly Dish: https://andrewsullivan.substack.com/ • Sinocism (Bill Bishop’s newsletter): https://sinocism.com/ • The Chatner (Daniel Lavery’s newsletter): https://www.thechatner.com/ • No one will ever read your book: https://www.elysian.press/p/publishin... • After Babel (Jonathan Haidt’s newsletter): https://www.afterbabel.com/ • Story Club with George Saunders: https://georgesaunders.substack.com/ • Substack Notes: https://support.substack.com/hc/en-us... • Substack: Empire of Narratives: https://thegeneralist.substack.com/p/... • Carla Lalli Music on Substack: https://carlalallimusic.substack.com/ • The Parnas Perspective: https://aaronparnas.substack.com/ • Baumol effect: https://en.wikipedia.org/wiki/Baumol_... ...Episode resources continued at: https://thegeneralist.substack.com/p/... Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].