The Generalist

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

May 6, 2025

Chris Best and Hamish McKenzie, co-founders of Substack, discuss how their platform empowers independent writers through a subscription model that fosters a direct creator-audience connection. They explore the impact of AI on creativity and contrast their approach with traditional media, highlighting a pivotal clash with Elon Musk that ultimately strengthened their vision. The conversation covers the transformative potential of Substack for diverse content creators and addresses the changing economics of the media landscape.

01:25:36

Creator website

Episode guests

Hamish McKenzie

Chris Best

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Episode notes

Podcast summary created with Snipd AI

Quick takeaways

Substack empowers creators by allowing them to monetize their work directly through paid subscriptions, promoting ownership and sustainable revenue streams.

The platform fosters a 'soul connection' between creators and audiences, emphasizing meaningful engagement amid an increasingly automated media landscape.

As AI enhances creative workflows, the demand for high-quality, value-driven content is expected to grow, significantly shifting consumer spending dynamics.

Deep dives

The Impact of Technology on Costs

Allowing technology, particularly AI, to be applied effectively makes processes better and cheaper. As society grows wealthier and more transactions occur, goods that remain untouched by technology become increasingly expensive, consuming a larger share of the economy. This shift raises questions about the future of media in an AI-driven environment, where cheap, mass-produced entertainment can overshadow more meaningful content. Ultimately, the challenge lies in navigating this new terrain to ensure that human judgment and personal values guide our engagement with media.

Intro

2min

Revolutionizing Media: The Intersection of AI and Creator Economics

5min

The Birth of Substack: Rethinking Media

8min

Building Substack: A Niche Approach to Creator Empowerment

21min

Substack vs. Social Media: A New Paradigm

14min

Rethinking Monetization: The Shift from YouTube to Substack

3min

Navigating Platform Dependency

4min

Navigating the Future of Media and Consumer Behavior

20min

Literature and Cultural Reflection

9min

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.
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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