Literature and Cultural Reflection

This chapter features a lively dialogue about the merits of prescribing books for others, exploring the tension between individual choice and cultural influence. The speakers delve into how literature reflects human truths and consider the impact of rituals and ancestral acknowledgment, especially through the lens of Māori traditions. Additionally, they speculate on how today's rapid technological changes may shape future historians' views of our current chaotic era.

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Episode notes

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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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.

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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