The Substack Playbook: Inside The $650M Platform Rewriting Media, Trust, and Creator Economics | Chris Best & Hamish McKenzie (Co-Founders)
The Substack Playbook: Inside The $650M Platform Rewriting Media, Trust, and Creator Economics | Chris Best & Hamish McKenzie (Co-Founders)  
Podcast: The Generalist
Published On: Tue May 06 2025
Description: 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 moreThank you to the partners who make this possibleVanta: Automate compliance and simplify security.Brex: The banking solution for startups.WorkOS: The modern identity platform for B2B SaaS.Explore the episodeTimestamps(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 meditationsFollow Chris BestX: https://x.com/cjgbestLinkedIn:https://www.linkedin.com/in/cjgbest/Follow Hamish McKenzieX: https://x.com/hamishmckenzieLinkedIn: https://www.linkedin.com/in/hamishmckenzie/Resources and episode mentionsBooks* The Anxious Generation: How the Great Rewiring of Childhood Is Causing an Epidemic of Mental Illness: https://www.amazon.com/Anxious-Generation-Rewiring-Childhood-Epidemic/dp/0593655036* The Canterbury Tales: https://www.amazon.com/Canterbury-Tales-Geoffrey-Chaucer/dp/0140424385People* Jairaj Sethi on LinkedIn: https://www.linkedin.com/in/jairaj-sethi/* Andrew Chen on LinkedIn: https://www.linkedin.com/in/andrewchen/* Mike Kerns on LinkedIn: https://www.linkedin.com/in/mike-kerns-63219/* Patrick Collison on LinkedIn: https://www.linkedin.com/in/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/publishing-industry-truth* 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/sections/14408747121940-Notes* Substack: Empire of Narratives: https://thegeneralist.substack.com/p/substack* Carla Lalli Music on Substack: https://carlalallimusic.substack.com/* The Parnas Perspective: https://aaronparnas.substack.com/* Baumol effect: https://en.wikipedia.org/wiki/Baumol_effect* Live video on Substack: https://support.substack.com/hc/en-us/articles/30316077882516-Getting-started-with-Live-Video-on-Substack* The Jim Acosta Show: * The Atlantic: https://www.theatlantic.com/* The Economist: https://www.economist.com/* The New Yorker: https://www.newyorker.com/* The Ankler: https://theankler.com/* The Bulwark: https://www.thebulwark.com/* The Free Press: https://substack.com/@thefreepressSubscribe to the showI’d love it if you’d subscribe and share the show. 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