It’s Alex Danco’s landmark 10th appearance on Infinite Loops!

He joins the show to discuss his move from Shopify to a16z (where he'll be building out their editorial operations), the power dynamics between VCs and founders (the kings and priests of our era), communication theory and the power of speechwriting, Reagan's rhetorical genius, authentic weirdos, America's hypomanic DNA, the unexpected similarities between American and Chinese culture, and why listeners who haven't read any recommended books after 10 episodes are wasting their time.

I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.

Important Links:

• Website
• Twitter
• Newsletter

Show Notes:

• Alex’s New Gig
• A Civil War Between Elites
• The Citizen Kane Test for CEOs
• Communication is the Founder's Job
• VCs as Legitimacy Banks & Magic-Makers
• The Lost Art of Speechwriting
• Reagan's Genius & The American Dream
• The Hypomanic Edge
• Mystery, Respect, and Cultural Power
• Marketing Ideas to the Right Audience
• The New Internet Economy
• Maritime Laws for AI Agents
• The Goth Index and Authenticity
• Substack's Identity Crisis & The Role of Podcasts
• Alex as Emperor of the World (Again)

Books Mentioned:

• What Works on Wall Street; by Jim O'Shaughnessy
• How Music Works; by David Byrne
• Breakneck: China’s Quest to Engineer the Future; by Dan Wang
• The Hypomanic Edge: The Link Between (A Little) Craziness and (A Lot of) Success in America; John D. Gartner
• The Language of Magic; by Toby Chapel
• Underwriters of the United States: How Insurance Shaped the American Founding; by Hannah Farber

Sangeet Paul Choudary, bestselling author of Platform Revolution and Reshuffle, and senior fellow at UC Berkeley, joins the show to challenge the conventional wisdom about AI's impact on our economy. We explore why knowledge workers risk falling "below the algorithm," how curiosity and judgment become luxury goods in a world of cheap answers, and why our educational and career structures need complete reinvention rather than incremental reform.

I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.

Important Links:

• Reshuffle: Who Wins When AI Restacks the Knowledge Economy (Amazon)
• Website
• Twitter
• Substack
• LinkedIn

Show Notes:

• Sangeet’s Core Thesis
• Technology's Second Order Effects
• Coordination Without Consensus
• Resistance to Innovation
• The Bottlenecks of Changing Systems
• Staying Above The Algorithm
• An Impending Cognitive Chasm
• The Limitations of Reskilling
• Redesigning Hiring for the AI Era
• The Human Touch Fallacy
• The End of Linear Career Paths
• Collective Sense-making in Uncertainty
• Sangeet as Emperor of the Day

Books Mentioned:

• Platform Revolution; by Geoffrey G Parker, Marshall W Van Alstyne, Sangeet Paul Choudary
• Reshuffle; by Sangeet Paul Choudary
• The Hound of the Baskervilles; by Arthur Conan Doyle
• Why Greatness Cannot Be Planned; by Kenneth Stanley and Joel Lehman

Michael Dean — architect-turned-writer, O’Shaughnessy Fellow, and creator of Essay Architecture — joins the show to explore the hidden structures beneath nonfiction and why essays, like buildings, can be designed with patterns rather than left to inspiration.

We discuss the origins of Essay Architecture, Michael’s 27-pattern framework that maps essays across Idea, Form, and Voice, and how to make craft teachable and AI feedback useful without replacing the writer. Along the way, we dive into architecture school critiques, why publishable doesn’t mean perfect, how editing rewires thinking, and the cultural risks if we keep treating writing as vibes instead of patterns.

I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.

Important Links:

• Michael’s Website
• Substack
• X/Twitter Profile

Show Notes:

• The Architecture of Essays: from Design School to Writing Frameworks
• The Pattern Language: Idea, Form, and Voice
• Local Nuance vs Global Stylekits
• Fundamentals before Breaking Rules: Joyce, Picasso, the Beatles
• Quality Without a Name
• Leveling the College Playing Field
• The Two Sandboxes of Fundamentals and Amplification
• Gamification, Play and Motivation
• Beyond the Five-paragraph Essay: Emerson and AI in Education
• Scoring Great Essays: Why David Foster Wallace takes Three Top Spots
• How Writing Colonized the brain
• Editing as Belief-rewiring: Why Writers Avoid It and Why Math Helps
• The King of Biases: Confirmation Bias
• Michael as Emperor of the World

Books Mentioned:

• Works on Wall Street; Jim O’Shaughnessy
• Essay Architecture (in progress) ; by Michael Dean
• A Pattern Language; by Christopher Alexander
• The Best American Essays 2024 Anthology; by Wesley Morris and Kim Dana Kupperman
• Consider the Lobster; by David Foster Wallace
• The White Album; by Joan Didion
• Shooting an Elephant; by George Orwell
• Portrait of an Artist as a Young Man; by James Joyce
• Finnegan’s Wake; by James Joyce
• Towards a Golden Age; Paul Graham
• The Limits of Scientific Reasoning; by David Faust
• The WEIRDest People in the World; by Joseph Henrich