Stewart Squared

In this episode of Stewart Squared, host Stewart Alsop explores the critical role of ontologies in computing with his father, guest Stewart Alsop II. The conversation covers how early internet pioneers like Yahoo and Amazon used ontologies to organize information, making it machine-readable, and examines whether companies like Apple might be leveraging ontological approaches for knowledge manageme...

In this episode of the Stewart Squared Podcast, host Stewart Alsop sits down with his father Stewart Alsop II for another fascinating father-son discussion about the tech industry. They dive into the Osborne effect - a business phenomenon from the early computer days where premature product announcements can destroy current sales - and explore how this dynamic is playing out in today's AI landscap...

In this episode of the podcast, host Stewart Alsop III engages in a wide-ranging conversation with Stewart Alsop II about data training, social media competition between X and Threads, and the broader technological landscape from semiconductors to AI. The discussion covers everything from Taiwan's dominance in chip manufacturing through TSMC, the evolution of supercomputers from Seymour Cray's inn...

In this episode of Stewart Squared, host Stewart Alsop III talks with his father, Stewart Alsop II, covering a wide range of technology topics from their unique generational perspective where the father often introduces cutting-edge tech to his millennial son rather than the reverse. The conversation spans from their experiences with Meta's Threads platform and its competition with X (formerly Twi...

In this episode of Stewart Squared, hosts Stewart Alsop and Stewart Alsop II explore the fascinating connections between 1960s counterculture and the birth of the PC industry, examining how figures like Nolan Bushnell bridged the gap between the Summer of Love and Silicon Valley innovation. The discussion traces the evolution from dedicated gaming computers like Atari's early machines to general-p...

In this episode, Stewart Alsop III sits down with Stewart Alsop II to unpack Google’s sudden return to the front of the AI race—touching on Gemini 3, Google’s Anti-Gravity IDE, the shifting outlook for OpenAI, Nvidia’s wobble, the strategic importance of TPUs, and the broader geopolitical currents shaping U.S.–China competition. Along the way, Stewart II reflects on leadership inside Google, the e...

In this episode of the Stewart Squared podcast, hosts Stewart Alsop II and Stewart Alsop III explore the evolution of Silicon Valley's regional dominance from the 1980s and 90s to today's AI-driven landscape. The conversation examines whether entrepreneurs still need to relocate to Silicon Valley to succeed, especially given that major AI companies like OpenAI, Anthropic, and Perplexity are all he...

In this episode, Stewart Alsop II and Stewart Alsop III sit down with Nolan Bushnell and Brent Bushnell for a wide-ranging conversation that moves from Atari’s countercultural roots to the realities of entrepreneurship, tinkering with hardware and AI, the rise of gamified education, and the creative traditions passed through families. Together they explore how curiosity, culture, and hands-on maki...

In this episode, Stewart Alsop III sits down with Stewart Alsop II to explore a wide sweep of themes—from getting an ESP32 and Arduino IDE up and running, to the future of physical AI, real-time computing, Starlink’s mesh network ambitions, and how edge devices like Apple’s upcoming M-series gear could shift the balance between local and cloud intelligence. Along the way, the two compare today’s r...

In this episode of Stewart Squared , Stewart Alsop sits down with his father, Stewart Alsop II, for a wide-ranging conversation that connects the dots between streaming, AI, and the deeper history of how computers came to shape our world. Together they trace the path from the early days of Mosaic and Netscape to today’s agentic browsers like Atlas, Comet, and Gemini, exploring how Google, Apple, a...

In this episode of Stewart Squared , hosts Stewart Alsop II and his son Stewart Alsop III, sits down with journalist and author Fred Vogelstein , known for his book Crazy Stupid Tech , to explore how technology, finance, and media are colliding in the age of AI. The conversation moves from Cloudflare’s emerging influence on AI web infrastructure and Google’s shifting search economy to the echoes o...

In this episode of Stewart Squared , Stewart Alsop III talks with his father, Stewart Alsop II , about Sam Altman’s $25 billion plan to build OpenAI data centers in Patagonia and how it connects to a broader U.S.–Argentina currency swap and the shifting landscape of AI geopolitics . Together, they unpack what this means for energy demand, chip supply, and U.S. influence abroad , drawing parallels...

In this episode of Stewart Squared , Stewart Alsop III sits down with his father, Stewart Alsop II , for a rich, cross-generational conversation about China’s technological ambitions and the shifting balance of global power in semiconductors, AI, and manufacturing. Together, they unpack how China achieved seven-nanometer chips without EUV, the dominance of TSMC and its partnership with Apple , the...

In this episode, Stewart Alsop III speaks with his father, Stewart Alsop II , about Hong Kong’s transformation since the 1997 handover and what it reveals about power, identity, and control in the information age. Together, they trace the shifting relationship between surveillance and sovereignty, explore how technology and data have become new instruments of hard power, and question what autonomy...

In this episode, Stewart Alsop II , Stewart Alsop III , Brent Bushnell , and a brief appearance by Nolan Bushnell come together for a thoughtful exchange about the evolution of immersive entertainment, mixed reality, and playful learning. The conversation touches on creativity through technology, the merging of physical and digital worlds, and the Bushnell family’s legacy of innovation across art,...

In this episode of Stewart Squared , Stewart Alsop sits down with his father, Stewart Alsop II, for a wide-ranging conversation that moves from OpenAI’s massive semiconductor and Oracle deals, to the nature of money and the gold standard, to shifting dynamics in U.S.–China relations and modern warfare technologies like drones and cyber tools. They also trace the history of networking and video gam...

In this episode of Stewart Squared , Stewart Alsop III sits down with Stewart Alsop II to talk about Cloudflare, its role as the “network administrator” of the internet, and how its business model connects to the larger shifts happening with AI, content, and regulation. The conversation moves through Cloudflare’s core services—CDN, DDoS protection, DNS, zero trust security, and more—before branchi...

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 of CapEx and depreciation schedules to the sustainability of investments by Microsoft, Meta, OpenAI, and Anthropic. The conversation traces historical precedents like the fiber boom, Google’s rise,...

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 Delaware dominates incorporation, and how governance plays out through independent directors and board structures. The conversation ranges from startup financing and information asymmetry to the U.S. g...

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 forces echo both in technology and politics. Our conversation weaves through corporate rivalries, the scaling challenges that shape giants of industry, and the geopolitical pressures facing nations l...

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 AI adoption, Google’s approach to knowledge management, and the broader lessons of technological hype cycles from fiber optics to GPT-5. Together they explore how big companies evolve from serving pr...

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 stretching back to Rome and the East India Company, the mechanics of preferred versus common shares in venture capital, and the recent Figma IPO. Along the way, they contrast speculation and perception...

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 HTTPS, reverse proxies, DNS integration, and zero-trust systems. The conversation weaves through the evolution of enterprise networking since the Cisco-dominated 1990s, the growth of server farms and...

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 the future of human imagination. They explore how Meow Wolf emerged from a decentralized art collective using recycled materials into a boundary-pushing, experience-driven company with hundreds of crea...

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 Meta’s domination of social platforms like Threads and Instagram. The Stewarts reflect on relevance in tech, the decline of platforms like Quora, the ascent of Substack, and the meaning of audience o...