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
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For a full transcript of the episode, please visit: https://thegeneralist.substack.com/p/the-substack-playbook
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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
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Follow Chris Best
X: https://x.com/cjgbest
LinkedIn:https://www.linkedin.com/in/cjgbest/
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Follow Hamish McKenzie
X: https://x.com/hamishmckenzie
LinkedIn: https://www.linkedin.com/in/hamishmckenzie/
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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/
...Resources continued at: https://thegeneralist.substack.com/p/the-substack-playbook
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The Generalist 
