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
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Explore the episode
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
LinkedIn:https://www.linkedin.com/in/cjgbest/
Follow Hamish McKenzie
X: https://x.com/hamishmckenzie
LinkedIn: https://www.linkedin.com/in/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-Generation-Rewiring-Childhood-Epidemic/dp/0593655036
The Canterbury Tales: https://www.amazon.com/Canterbury-Tales-Geoffrey-Chaucer/dp/0140424385
People
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/@thefreepress
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