Shows / Stewart Squared
Stewart Squared
Stewart Alsop III reviews a broad range of topics with his father Stewart Alsop II, who started his career in the personal computer industry and is still actively involved in investing in startup technology companies. Stewart Alsop III is fascinated by what his father was doing as SAIII was growing up in the Golden Age of Silicon Valley. Topics include: - How the personal computing revolution led to the internet, which led to the mobile revolution - Now we are covering the future of the…
Episodes
Stewart SquaredEpisode #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…
Stewart SquaredEpisode #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…
Stewart SquaredEpisode #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…
Stewart SquaredEpisode #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…
Stewart SquaredEpisode #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…
Stewart SquaredEpisode #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…
Stewart SquaredEpisode #47: The Cost of Knowing Everything
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they navigate a sprawling conversation that begins with the unruly complexity…
Stewart SquaredEpisode #46: Bubble Logic: Why AGI and Drones Feel Inevitable
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore the OpenAI–Microsoft partnership through the lens of historic…
Stewart SquaredEpisode #45: Natural Language as the New Operating System
Welcome to Stewart Squared podcast with the two Stewart Alsops, where they explore the evolution of software from 1.0’s “magical incantations” to 3.0’s natural…
Stewart SquaredEpisode #44: Consultants Preach, AI Learns, and CEOs Fall Behind
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore why consultants often fail in the tech world, how leadership…
Stewart SquaredEpisode #43: Meme Coins and Moon Mines: Surveillance in the Age of Trump and Musk
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this wide-ranging conversation, the Stewarts kick off with a personal dive into the early…
Stewart SquaredEpisode #42: The Myth of Openness in a Dualistic Valley
Welcome to Stewart Squared podcast with the two Stewart Alsops. This episode navigates the arc of the Internet’s transformation from the promise of an open…
Stewart SquaredEpisode #41: Homebrew Aftershocks: Echoes from the Pre-Platform Era
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, father and son trace the tectonic shifts that shaped Silicon Valley—from the…
Stewart SquaredEpisode #40: Probabilistic Machines: Living with the Illusion of Control
Welcome to Stewart Squared podcast with the two Stewart Alsops, where this episode takes you on a ride through vibe coding experiments, AI-powered doom loops…
Stewart SquaredEpisode #39: Trust Issues: From Meme Coins to Mainframes
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, we talk about what happened to trust—why it’s gone, where it went, and whether…
Stewart SquaredEpisode #38: From IBM to AI: How Business Lost Its Mind and Found the Algorithm
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they track the transformation of business from the IBM-dominated 1980s to…
Stewart SquaredEpisode #37: Elegance vs. Exquisite: Rethinking Systems Old and New
I, Stewart Alsop, was absolutely thrilled to have my dad, Stewart Alsop II, and our very special guest, Gilman Louie, on this episode of Crazy Wisdom. We…
Stewart SquaredEpisode #36: Tiny Computers, Massive Shifts: The iPhone’s Quiet Coup
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation ranges across the years that saw Apple shift from a…
Stewart SquaredEpisode #35: From the Great Society to the Great Fragmentation
Welcome to Stewart Squared podcast with the two Stewart Alsops. Today’s episode moves beyond technology to explore a deeply personal and historical reflection…
Stewart SquaredEpisode #34: From Magellan to the Machine: Bill Gross on the Search for Meaning
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this wide-ranging conversation, they’re joined by legendary entrepreneur and Idealab founder…
Stewart SquaredEpisode #33: From Mainframes to Minds: Rethinking the Architecture of Intelligence
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation starts with a personal quest into vector databases and linked…
Stewart SquaredEpisode #32: Startups, Deadlines, and Drift: The Venture Logic Behind Modern Newsrooms
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation weaves through the evolution of media, venture capital’s long…
Stewart SquaredEpisode #31: Satya’s Quiet Coup: How Microsoft Got Its Groove Back
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they unpack the rise of Satya Nadella and how his leadership reshaped…
Stewart SquaredEpisode #30: From InfoWorld to x.com: The Patterns That Repeat
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation winds through a rich mix of personal history, editorial…
Stewart SquaredEpisode #29: Bridging the Physical and Digital: Investing in the Next Big Shift
Welcome to Stewart Squared podcast with the two Stewart Alsops, featuring special guest Jim Ward. In this episode, Jim shares insights on the "third…
Stewart SquaredEpisode #28: How to do world building?
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore the evolution of technology from the rise of the PC, internet…
Stewart SquaredEpisode #27: From Napster to OpenAI: The Relentless Disruption of Everything
Welcome to the Stewart Squared podcast with the two Stewart Alsops. In this episode, we explore the concept of "convergences" in technology, focusing on the…
Stewart SquaredEpisode #26: Steve Case on the Internet’s Wild Ride and What’s Next
Welcome to Stewart Squared podcast with the two Stewart Alsops. Today’s guest is Steve Case, former CEO of AOL and the founder of Revolution. In this episode…
Stewart SquaredEpisode #25: The Third Convergence: When Reality and Digital Collide
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, we explore the concept of the Third Convergence, a period from 2025 to 2045…
Stewart SquaredEpisode #24: From Ethernet to AGI: Tracing the Threads of Connection
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, we explore the evolution of networking—from the early days of isolated…
Stewart SquaredEpisode #23: Big Tech, Big Government, and the Coming War Over Power
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, we break from our usual focus on technology and innovation to discuss the…
Stewart SquaredEpisode #22: Seeing the World Differently: Psychedelics, Media, and Modern Humanism
Welcome to the Stewart Squared podcast with the two Stewart Alsops! Today’s conversation intertwines the evolution of technology—from the rise of the PC and…
Stewart SquaredEpisode #21: History on Repeat: Lessons from Electricity to AI
Welcome to Stewart Squared podcast with the two Stewart Alsops! Today, we’re cruising along the Pacific Coast Highway with the ocean on one side and mountains…
Stewart SquaredEpisode #20: Old Giants vs. New Titans: SpaceX, Legacy Contractors, and the Cost of Progress
Welcome to Stewart Squared podcast with the two Stewart Alsops! In this special episode, recorded on a scenic drive up the 101 from Los Angeles to Santa…
Stewart SquaredEpisode #19: The DNA of Insight: Generational Lessons in Innovation and Communication
Welcome to the Stewart Squared podcast with the two Stewart Alsops! In this special episode, recorded while driving up the 101 from Los Angeles to Santa…
Stewart SquaredEpisode #18: Why Innovation Needs Leadership: Stories from Silicon Valley and Beyond
Welcome to Stewart Squared Podcast with the two Stewart Alsops! In this episode, the conversation spans decades of technological evolution, starting with the…
Stewart SquaredEpisode #17: From California to Buenos Aires: Gaming Bureaucracies in the Digital Age
Welcome to Stewart Squared podcast with the two Stewart Alsops! This episode explores the fascinating concept of residency hacking, blending digital nomadism…
Stewart SquaredEpisode #16: From TiVo to TikTok: TV Tech That Changed How We See the World
Welcome to Stewart Squared podcast with the two Stewart Alsops. This episode takes listeners on a tour through television’s evolution, touching on the birth of…
Stewart SquaredEpisode #15: Why Gen Z Thinks Differently: Growing Up in a World That Never Logs Off
Welcome to the Stewart Squared podcast with the two Stewart Alsops! In today’s episode, the Stewarts dive into the rapid evolution of tech, from Apple's…
Stewart SquaredEpisode #14: How We Got Here: A Journey Through Tech’s Defining Waves
Welcome to Stewart Squared podcast with the two Stewart Alsops! This week’s episode takes you through decades of technological evolution, from Stewart Alsop…
Stewart SquaredEpisode #13: AI Hype vs. Reality: Cutting Through the Noise
Welcome to Stewart Squared podcast with the two Stewart Alsops! In this episode, we tackle the evolution and current state of artificial intelligence, with…
Stewart SquaredEpisode #12: The New Rules of Tech: From 90s Antitrust to Today’s AI Dilemma
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they dive into a fascinating discussion on the intersection of personal…
Stewart SquaredEpisode #11: The Internet’s Genesis: How the 1990s Opened the Floodgates of Innovation
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, Stewart Alsop III and his father, Stewart Alsop II, take a deep dive into the…
Stewart SquaredEpisode #10: Forty Years Later: Are We Finally There with AI?
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore the trajectory of technology from the early days of personal…
Stewart SquaredEpisode #9: The AI Whisperer: A New Era of Prompt-Based Programming
Welcome to the Stewart Squared podcast with the two Stewart Alsops, featuring special guest Joe Alsop. This episode covers the evolution of technology from the…
Stewart SquaredEpisode #8: The Rise of Personal Computing and the Fall of Trust
Welcome to Stewart Squared Podcast with the two Stewart Alsops. In this episode, they explore the early personal computing revolution, beginning with the rise…
Stewart SquaredEpisode #7: Satellites, Warfare, and the End of Terrestrial Tech
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore pivotal moments in technology, starting with the personal…
Stewart SquaredEpisode #6: Evernet Dreams: The Intersection of Satellite Tech, Battery Innovation, and Constant Connectivity
Welcome to Stewart Squared podcast with the two Stewart Alsops! In this episode, they dive into the history of personal computing, the evolution of the…
Stewart SquaredEpisode #5: Silicon Valley's Dark Horse: Oracle’s Past, Present, and Future
Welcome to the Stewart Squared podcast with the two Stewart Alsops. In this episode, the discussion takes a deep dive into the intriguing history and current…
Stewart SquaredEpisode #4: Building Giants and Guarding Integrity: Lessons from the Tech Trenches
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, we continue our exploration of fiduciary responsibility within the realms of…
Stewart SquaredEpisode #3: San Francisco: The Empire at Its Peak or on the Brink?
Welcome to the Stewart Squared podcast with the two Stewart Alsops! In this episode, Stewart Alsop II and Stewart Alsop III discuss the complexities of San…
Stewart SquaredEpisode #2: The Evolution of Computing: a Generational Conversation
Welcome to the Stewart Squared podcast with the two Stewart Alsops interviewing Joe Alsop who started Progress Software and took it all the way to IPO. In this…
Stewart SquaredConferences: Why do people start them?
In this episode of Crazy Wisdom's special series, Stewart Squared, Stewart Alsop III and his father Stewart Alsop II delve into various topics. They discuss…