
Inside Substack’s $650M Playbook for the Future of Media (Chris Best & Hamish McKenzie, Co-Founders)
The GeneralistShow 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 — 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 [email protected].
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Pete Florence and I began by agreeing that his company has an excellent name. Generalist builds AI for robots, including models that can begin learning a new task from a single demonstration. We talked about dexterity, the strange business of gathering physical experience for a machine, and what we might build if robots could do much more of the work. — Every timestamp 00:00 Intro 02:24 GEN-1.5 and one-shot learning 08:55 What makes a task difficult 10:53 Dexterity in robotics 14:53 Matt Mason’s definition of a hand 17:34 Giving robots a sense of touch 20:30 Growing up in a family of technologists and scientists 22:46 What drew Pete into robotics 27:38 Generalist’s founding thesis and what sets it apart 32:17 Protecting simplicity 35:01 How Generalist’s data collection has evolved 35:30 Generalist’s scaling philosophy 39:53 Generalist’s build-versus-buy philosophy 42:15 Balancing general intelligence with commercial deployment 44:24 Why Pete is betting on dexterity 47:33 The durability of the robotics application layer 49:09 Open-weight robotics models and data flywheels 50:52 Geopolitics, safety, and alignment 52:42 The parallels between teaching humans and robots 1:00:05 The timeline for robotics progress and adoption 1:03:37 Book recommendations — Transcript: https://www.generalist.com/i/220756708/transcript — Pete’s complete reading list The Score Takes Care of Itself: My Philosophy of Leadership: https://www.amazon.com/Score-Takes-Care-Itself-Philosophy/dp/1591843472 Wooden on Leadership: How to Create a Winning Organization: https://www.amazon.com/Wooden-Leadership-Create-Winning-Organization/dp/0071453393 — Other resources Generalist: https://generalistai.com GEN-1.5: https://generalistai.com/blog/gen-1.5 Proprioception: https://en.wikipedia.org/wiki/Proprioception Cutaneous receptor: https://en.wikipedia.org/wiki/Cutaneous_receptor Fukushima nuclear accident: https://en.wikipedia.org/wiki/Fukushima_nuclear_accident The bitter lesson: https://www.cs.utexas.edu/~eunsol/courses/data/bitter_lesson.pdf GEN-1: https://generalistai.com/blog/gen-1 — Where to find Pete Florence LinkedIn: https://www.linkedin.com/in/peteflorence X: https://x.com/peteflorence Website: https://www.peteflorence.com — Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].
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