Episode #55: From Justin.tv to Claude Hacks: Lessons in Tech, Money, and Security
In this episode of Stewart Squared, Stewart Alsop III sits down with Stewart Alsop II to explore the financial and technical foundations shaping today’s AI and cloud economy, from the staggering scale...
18 Sep 202557min
Episode #54: Preference Stacks, Power Games, and the Future of War
In this episode of Stewart Squared, Stewart Alsop III and Stewart Alsop II explore the mechanics of the preference stack in venture investing, the difference between economic and voting rights, why De...
11 Sep 202544min
Episode #53: Cycles of Scaling: How AI and Politics Break Systems
In this episode of Crazy Wisdom, I, Stewart Alsop III, talk with my father, Stewart Alsop II, about the surprising reception of ChatGPT, the role of AI as a modern chaos agent, and the ways disruptive...
4 Sep 202554min
Episode #52: The Illusion of Choice in Big Tech
In this episode of Stewart Squared, Stewart Alsop sits down with his father, Stewart Alsop II, for a wide-ranging conversation on the frustrations of modern UI/UX, Microsoft’s struggles with spam and ...
28 Aug 202552min
Episode #51: Ray-Bans, Apple Stock, and the Long Game of Power and Timing
In this episode of Stewart Squared, both Stewarts have a wide-ranging conversation that jumps from Claude and Anthropic’s aggressive move against OpenAI employees to the deep history of corporations s...
21 Aug 202556min
Episode #50: Star Hubs, Server Farms, and the Strange New Geography of AI
In this episode, Stewart Alsop III talks with Stewart Alsop II about Cloudflare’s role in modern internet infrastructure, from its origins with Project Honeypot to its massive global network powering ...
14 Aug 202557min
Episode #49: The Next Internet Is Immersive Experience
In this episode of Stewart Squared, host Stewart Alsop talks with Vince Kadlubek, founder and Chief Vision Officer of Meow Wolf, about the evolution of immersive art, post-capitalist creativity, and t...
7 Aug 202557min
Episode #48: The Slow Death of Social Media (And What Comes Next)
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation orbits around the mechanics and ethics of digital walled gardens, from YouTube’s curated algorithms to...
31 Jul 202535min
