Stewart Squared
Episodes
Episode #83: The Focus Layer: Why Anthropic, NVIDIA, and Cloudflare Are Winning the Same War
02 Apr 2026
Contributed by Lukas
In this episode of Stewart Squared, host Stewart Alsop III and his father Stewart Alsop II cover a wide range of interconnected topics, starting with ...
Episode #82: What Happens When You Stop Trusting Platforms and Start Building Your Own
26 Mar 2026
Contributed by Lukas
Stewart Alsop is joined by his guest, Stewart Alsop II, for a wide-ranging conversation about the technology behind modern podcasting and streaming, s...
Episode #81: Indoor, Outdoor, In Between: The Real Future of Human Experience
19 Mar 2026
Contributed by Lukas
In this episode of Stewart Squared, host Stewart Alsop III is joined by his co-host Stewart Alsop II to cover a wide range of topics stemming from Ste...
Episode #80: The Unreal Engine of Everything: Betting on the Next Shift in Entertainment
12 Mar 2026
Contributed by Lukas
In this episode of Stewart Squared, host Stewart Alsop is joined by his longtime co-host and guest Stewart Alsop II to cover a wide range of topics sp...
Episode #79: Inside the Collision: Where AI, Hollywood, and the US Government Are All Breaking at Once
05 Mar 2026
Contributed by Lukas
In this episode of Stewart Squared, host Stewart Alsop III sits down with his father Stewart Alsop II — veteran tech journalist turned venture capit...
Episode #78: The Vibe Coding Takeover: How Bot Swarms Are Turning SaaS Into an Endangered Species
26 Feb 2026
Contributed by Lukas
In this episode of the Stewart Squared podcast, Stewart Alsop turns the tables on his usual role as host, handing the reins to his father Stewart Also...
Episode #77: The Napster Effect: Why the Old Guard Always Loses
19 Feb 2026
Contributed by Lukas
In this episode of the Stewart Squared podcast, host Stewart Alsop III sits down with his father Stewart Alsop II to explore the evolution of print me...
Episode #76: Dear Hollywood, Give Up: Lessons from Napster, Netflix, and the Inevitable
12 Feb 2026
Contributed by Lukas
In this episode of the Stewart Squared podcast, host Stewart Alsop III speaks with his father Stewart Alsop II about the ongoing battle between Hollyw...
Episode #75: The Real-Time Problem: Why LLMs Hit a Wall and World Models Won't
05 Feb 2026
Contributed by Lukas
In this episode of the Stewart Squared podcast, host Stewart Alsop III sits down with his father Stewart Alsop II to explore the emerging field of wor...
Episode #74: From Cold War to AI War: Navigating Power, Surveillance, and the Future of Democracy
29 Jan 2026
Contributed by Lukas
In this episode of the Stewart Squared podcast, host Stewart Alsop sits down for a wide-ranging conversation that starts with insurance concepts but q...
Episode #73: The Network Effect: How We Went from Manual Data Transfer to Global Information Warfare
22 Jan 2026
Contributed by Lukas
In this wide-ranging episode of Stewart Squared, host Stewart Alsop sits down with his guest Stewart Alsop II to explore everything from the surprisin...
Episode #72: From Yahoo's Directory to Apple's Neural Chips: The Evolution of Structured Knowledge
15 Jan 2026
Contributed by Lukas
In this episode of Stewart Squared, host Stewart Alsop explores the critical role of ontologies in computing with his father, guest Stewart Alsop II. ...
Episode #71: The AI Momentum Trap: When Venture Models Replace Business Models
08 Jan 2026
Contributed by Lukas
In this episode of the Stewart Squared Podcast, host Stewart Alsop sits down with his father Stewart Alsop II for another fascinating father-son discu...
Episode #70: From Twitter to Threads: Escaping the Training Data Mines of Late Capitalism
01 Jan 2026
Contributed by Lukas
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 ...
Episode #69: From Floppy Disks to Claude Code: Riding the AI Dragon
25 Dec 2025
Contributed by Lukas
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 th...
Episode #68: Hot Tubs, Suits, and Silicon Souls: When Counterculture Built Computers
18 Dec 2025
Contributed by Lukas
In this episode of Stewart Squared, hosts Stewart Alsop and Stewart Alsop II explore the fascinating connections between 1960s counterculture and the ...
Episode #67: The Early Indicators: Will Google or OpenAI Dominate the Next Decade of AI?
11 Dec 2025
Contributed by Lukas
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...
Episode #66: The Randomness Engine: Why Silicon Valley Can't Be Cloned (And Why That Matters for AI)
04 Dec 2025
Contributed by Lukas
In this episode of the Stewart Squared podcast, hosts Stewart Alsop II and Stewart Alsop III explore the evolution of Silicon Valley's regional domina...
Episode #65: From Strawberries to Silicon Valley: The Origin Story of Atari’s Mindset
27 Nov 2025
Contributed by Lukas
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 fro...
Episode #64: The Last Mile of Intelligence: Real-Time Systems and Hardware Leap
20 Nov 2025
Contributed by Lukas
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 ru...
Episode #63: From Mosaic to Gemini: The Evolution of How We Connect
13 Nov 2025
Contributed by Lukas
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 ...
Episode #62: From Cloudflare to Chaos: Mapping the Fault Lines of the AI Economy
06 Nov 2025
Contributed by Lukas
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 ...
Episode #61: Powering the Machine: Altman, Milei, and the Energy Behind AI’s Future
30 Oct 2025
Contributed by Lukas
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 d...
Episode #60: Manufacturing Intelligence: A Conversation on Apple, TSMC, and China’s Playbook
23 Oct 2025
Contributed by Lukas
In this episode of Stewart Squared, Stewart Alsop III sits down with his father, Stewart Alsop II, for a rich, cross-generational conversation about C...
Episode #59: When Information Became the New Empire
16 Oct 2025
Contributed by Lukas
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 re...
Episode #58: Inventing Wonder: A Conversation with the Bushnells
09 Oct 2025
Contributed by Lukas
In this episode, Stewart Alsop II, Stewart Alsop III, Brent Bushnell, and a brief appearance by Nolan Bushnell come together for a thoughtful exchange...
Episode #57: Silicon, Sovereignty, and Speculation: The Stakes of AI’s Next Phase
02 Oct 2025
Contributed by Lukas
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’...
Episode #56: The Internet’s Business Model Is Cracking..What Comes Next?
25 Sep 2025
Contributed by Lukas
In this episode of Stewart Squared, Stewart Alsop III sits down with Stewart Alsop II to talk about Cloudflare, its role as the “network administrat...
Episode #55: From Justin.tv to Claude Hacks: Lessons in Tech, Money, and Security
18 Sep 2025
Contributed by Lukas
In this episode of Stewart Squared, Stewart Alsop III sits down with Stewart Alsop II to explore the financial and technical foundations shaping today...
Episode #54: Preference Stacks, Power Games, and the Future of War
11 Sep 2025
Contributed by Lukas
In this episode of Stewart Squared, Stewart Alsop III and Stewart Alsop II explore the mechanics of the preference stack in venture investing, the dif...
Episode #53: Cycles of Scaling: How AI and Politics Break Systems
04 Sep 2025
Contributed by Lukas
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 A...
Episode #52: The Illusion of Choice in Big Tech
28 Aug 2025
Contributed by Lukas
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 ...
Episode #51: Ray-Bans, Apple Stock, and the Long Game of Power and Timing
21 Aug 2025
Contributed by Lukas
In this episode of Stewart Squared, both Stewarts have a wide-ranging conversation that jumps from Claude and Anthropic’s aggressive move against Op...
Episode #50: Star Hubs, Server Farms, and the Strange New Geography of AI
14 Aug 2025
Contributed by Lukas
In this episode, Stewart Alsop III talks with Stewart Alsop II about Cloudflare’s role in modern internet infrastructure, from its origins with Proj...
Episode #49: The Next Internet Is Immersive Experience
07 Aug 2025
Contributed by Lukas
In this episode of Stewart Squared, host Stewart Alsop talks with Vince Kadlubek, founder and Chief Vision Officer of Meow Wolf, about the evolution o...
Episode #48: The Slow Death of Social Media (And What Comes Next)
31 Jul 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation orbits around the mechanics and ethics of digital wa...
Episode #47: The Cost of Knowing Everything
24 Jul 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they navigate a sprawling conversation that begins with the unruly co...
Episode #46: Bubble Logic: Why AGI and Drones Feel Inevitable
17 Jul 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore the OpenAI–Microsoft partnership through the lens of h...
Episode #45: Natural Language as the New Operating System
10 Jul 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops, where they explore the evolution of software from 1.0’s “magical incantations” t...
Episode #44: Consultants Preach, AI Learns, and CEOs Fall Behind
03 Jul 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore why consultants often fail in the tech world, how leader...
Episode #43: Meme Coins and Moon Mines: Surveillance in the Age of Trump and Musk
26 Jun 2025
Contributed by Lukas
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...
Episode #42: The Myth of Openness in a Dualistic Valley
19 Jun 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. This episode navigates the arc of the Internet’s transformation from the promise of ...
Episode #41: Homebrew Aftershocks: Echoes from the Pre-Platform Era
12 Jun 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, father and son trace the tectonic shifts that shaped Silicon Valley—...
Episode #40: Probabilistic Machines: Living with the Illusion of Control
05 Jun 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops, where this episode takes you on a ride through vibe coding experiments, AI-powered doo...
Episode #39: Trust Issues: From Meme Coins to Mainframes
29 May 2025
Contributed by Lukas
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...
Episode #38: From IBM to AI: How Business Lost Its Mind and Found the Algorithm
22 May 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they track the transformation of business from the IBM-dominated 1980...
Episode #37: Elegance vs. Exquisite: Rethinking Systems Old and New
15 May 2025
Contributed by Lukas
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....
Episode #36: Tiny Computers, Massive Shifts: The iPhone’s Quiet Coup
08 May 2025
Contributed by Lukas
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 ...
Episode #35: From the Great Society to the Great Fragmentation
01 May 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. Today’s episode moves beyond technology to explore a deeply personal and historical ...
Episode #34: From Magellan to the Machine: Bill Gross on the Search for Meaning
24 Apr 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this wide-ranging conversation, they’re joined by legendary entrepreneur and Idea...
Episode #33: From Mainframes to Minds: Rethinking the Architecture of Intelligence
18 Apr 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation starts with a personal quest into vector databases a...
Episode #32: Startups, Deadlines, and Drift: The Venture Logic Behind Modern Newsrooms
10 Apr 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation weaves through the evolution of media, venture capit...
Episode #31: Satya’s Quiet Coup: How Microsoft Got Its Groove Back
03 Apr 2025
Contributed by Lukas
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...
Episode #30: From InfoWorld to x.com: The Patterns That Repeat
27 Mar 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation winds through a rich mix of personal history, editor...
Episode #29: Bridging the Physical and Digital: Investing in the Next Big Shift
20 Mar 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops, featuring special guest Jim Ward. In this episode, Jim shares insights on the "third c...
Episode #28: How to do world building?
13 Mar 2025
Contributed by Lukas
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, int...
Episode #27: From Napster to OpenAI: The Relentless Disruption of Everything
07 Mar 2025
Contributed by Lukas
Welcome to the Stewart Squared podcast with the two Stewart Alsops. In this episode, we explore the concept of "convergences" in technology, focusing ...
Episode #26: Steve Case on the Internet’s Wild Ride and What’s Next
27 Feb 2025
Contributed by Lukas
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 thi...
Episode #25: The Third Convergence: When Reality and Digital Collide
13 Feb 2025
Contributed by Lukas
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 t...
Episode #24: From Ethernet to AGI: Tracing the Threads of Connection
06 Feb 2025
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, we explore the evolution of networking—from the early days of isola...
Episode #23: Big Tech, Big Government, and the Coming War Over Power
31 Jan 2025
Contributed by Lukas
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...
Episode #22: Seeing the World Differently: Psychedelics, Media, and Modern Humanism
23 Jan 2025
Contributed by Lukas
Welcome to the Stewart Squared podcast with the two Stewart Alsops! Today’s conversation intertwines the evolution of technology—from the rise of ...
Episode #21: History on Repeat: Lessons from Electricity to AI
16 Jan 2025
Contributed by Lukas
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...
Episode #20: Old Giants vs. New Titans: SpaceX, Legacy Contractors, and the Cost of Progress
09 Jan 2025
Contributed by Lukas
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 San...
Episode #19: The DNA of Insight: Generational Lessons in Innovation and Communication
05 Dec 2024
Contributed by Lukas
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 San...
Episode #18: Why Innovation Needs Leadership: Stories from Silicon Valley and Beyond
28 Nov 2024
Contributed by Lukas
Welcome to Stewart Squared Podcast with the two Stewart Alsops! In this episode, the conversation spans decades of technological evolution, starting w...
Episode #17: From California to Buenos Aires: Gaming Bureaucracies in the Digital Age
25 Nov 2024
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops! This episode explores the fascinating concept of residency hacking, blending digital n...
Episode #16: From TiVo to TikTok: TV Tech That Changed How We See the World
14 Nov 2024
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. This episode takes listeners on a tour through television’s evolution, touching on t...
Episode #15: Why Gen Z Thinks Differently: Growing Up in a World That Never Logs Off
07 Nov 2024
Contributed by Lukas
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 App...
Episode #14: How We Got Here: A Journey Through Tech’s Defining Waves
31 Oct 2024
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops! This week’s episode takes you through decades of technological evolution, from Stewa...
Episode #13: AI Hype vs. Reality: Cutting Through the Noise
24 Oct 2024
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops! In this episode, we tackle the evolution and current state of artificial intelligence,...
Episode #12: The New Rules of Tech: From 90s Antitrust to Today’s AI Dilemma
17 Oct 2024
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they dive into a fascinating discussion on the intersection of person...
Episode #11: The Internet’s Genesis: How the 1990s Opened the Floodgates of Innovation
10 Oct 2024
Contributed by Lukas
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 ...
Episode #10: Forty Years Later: Are We Finally There with AI?
03 Oct 2024
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore the trajectory of technology from the early days of pers...
Episode #9: The AI Whisperer: A New Era of Prompt-Based Programming
26 Sep 2024
Contributed by Lukas
Welcome to the Stewart Squared podcast with the two Stewart Alsops, featuring special guest Joe Alsop. This episode covers the evolution of technology...
Episode #8: The Rise of Personal Computing and the Fall of Trust
19 Sep 2024
Contributed by Lukas
Welcome to Stewart Squared Podcast with the two Stewart Alsops. In this episode, they explore the early personal computing revolution, beginning with ...
Episode #7: Satellites, Warfare, and the End of Terrestrial Tech
12 Sep 2024
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore pivotal moments in technology, starting with the persona...
Episode #6: Evernet Dreams: The Intersection of Satellite Tech, Battery Innovation, and Constant Connectivity
05 Sep 2024
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops! In this episode, they dive into the history of personal computing, the evolution of th...
Episode #5: Silicon Valley's Dark Horse: Oracle’s Past, Present, and Future
29 Aug 2024
Contributed by Lukas
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 ...
Episode #4: Building Giants and Guarding Integrity: Lessons from the Tech Trenches
22 Aug 2024
Contributed by Lukas
Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, we continue our exploration of fiduciary responsibility within the re...
Episode #3: San Francisco: The Empire at Its Peak or on the Brink?
15 Aug 2024
Contributed by Lukas
Welcome to the Stewart Squared podcast with the two Stewart Alsops! In this episode, Stewart Alsop II and Stewart Alsop III discuss the complexities o...
Episode #2: The Evolution of Computing: a Generational Conversation
08 Aug 2024
Contributed by Lukas
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...
Conferences: Why do people start them?
13 Jul 2024
Contributed by Lukas
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 d...