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

Vanta: Automate compliance and simplify security.
Brex: The banking solution for startups.
WorkOS: The modern identity platform for B2B SaaS.

—

For a full transcript of the episode, please visit: https://thegeneralist.substack.com/p/the-substack-playbook

—

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/

...Resources continued at: https://thegeneralist.substack.com/p/the-substack-playbook

—

Production and marketing by penname.co. For inquiries about sponsoring the podcast, email jordan@penname.co.