The Substack Playbook: Inside The $650M Platform Rewriting Media, Trust, and Creator Economics | Chris Best & Hamish McKenzie (Co-Founders)

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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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: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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