In this week’s episode of The Generalist podcast, I’m joined by Substack founders Chris Best and Hamish McKenzie. 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, @cjgbest and @hamishmckenzie are taking a radically different approach with @SubstackInc. 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. Listen now: • YouTube: • @spotifypodcasts: • Apple: A big thank you to the incredible sponsors that make the podcast possible: ✨ Vanta — Automate compliance and simplify security: ✨ Brex — The banking solution for startups: ✨ WorkOS — The modern identity platform for B2B SaaS: 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 … And much more!