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 #113: The Infinite Slop Cannon in the Sky: How Elon's Building His Empire
In this episode of the Stewart Squared podcast, host Stewart Alsop and his son Stewart Alsop II explore the convergence of autonomous robotics, corporate…
Stewart SquaredEpisode #112: From the PC to the Robot Dog: How Do Normal People Get Through the Next Shift?
In this episode of the Stewart Squared podcast, Stewart Alsop III sits down with his father, Stewart Alsop II, to unpack the intersection of AI agents and…
Stewart SquaredEpisode #111: Anthropic's IPO Comes With an Existential Risk Warning
In this episode of the Stewart Squared podcast, host Stewart Alsop sits down with his father, Stewart Alsop II, to dig into Anthropic's IPO filing, whose…
Stewart SquaredEpisode #110: Trust, Debt, and Foundation Models: The New Global Competition
In this episode of the Stewart Squared podcast, host Stewart Alsop sits down with his father Stewart Alsop II to explore the rapidly evolving landscape of AI…
Stewart SquaredEpisode #109: Are We Building the Dark Fiber of AI?
In this episode of the Stewart Squared podcast, host Stewart Alsop sits down with his son, Stewart Alsop II, to unpack Anthropic's anticipated IPO and the…
Stewart SquaredEpisode #108: Cybersecurity vs. Existential Risk: What Anthropic Won't Tell You in Their IPO
In this episode of the Stewart Squared podcast, host Stewart Alsop and his father Stewart Alsop II tackle the pressing issue of cybersecurity in AI…
Stewart SquaredEpisode #107: $2 Trillion, No Debt: Anthropic's Answer to SpaceX's Risk Factors
In this episode of the Stewart Squared podcast, host Stewart Alsop and guest Stewart Alsop II dig into Anthropic's upcoming IPO and the rapidly shifting…
Stewart SquaredEpisode #106: The $30 Trillion Question: Inside Anthropic's Audacious IPO Play
In this episode of the Stewart Squared podcast, host Stewart Alsop and guest Stewart Alsop II tackle Anthropic's upcoming IPO and what it means for the broader…
Stewart SquaredEpisode #105: Beating OpenAI at Their Own Game: Our Case, and the Filing That Settles It
In this episode of the Stewart Squared podcast, host Stewart Alsop III and his father Stewart Alsop II dig into the unprecedented AI infrastructure buildout…
Stewart SquaredEpisode #104: 36,000 Companies, One Metric: What DPI Did to Private Equity
In this episode of the Stewart Squared podcast, host Stewart Alsop sits down with his father Stewart Alsop II to unpack how private equity, venture capital…
Stewart SquaredEpisode #103: Scarce to Itself: NVIDIA, Apple, a Driverless Zoox, and the Real Fight Over the Future of Cars
In this episode of Stewart Squared, Stewart Alsop III and Stewart Alsop II dig into the fast-moving world of self-driving cars — from Cruise's rocky history…
Stewart SquaredEpisode #102: AI Is Eating the World’s Memory
In this episode of Stewart Squared, Stewart Alsop III and Stewart Alsop II sit into the shifting ground beneath the AI boom, starting with the strange saga of…
Stewart SquaredEpisode #101: Apple's AI Is Finally Here. Why Does It Still Feel Broken?
In this episode of the Stewart Squared podcast, hosts Stewart Alsop and Stewart Alsop II dig into Apple's rocky iOS 27 rollout and the Apple Intelligence…
Stewart SquaredEpisode #100: From Apple's iOS 27 to Anduril's Defense Tech: Where AI's Advantage Really Lies
In this episode of Stewart Squared, Stewart Alsop III sits down with his father and co-host Stewart Alsop II for a wide-ranging conversation that jumps from…
Stewart SquaredEpisode #99: Can Money Buy Meta a Comeback in AI?
In this episode of the Stewart Squared podcast, host Stewart Alsop and guest Stewart Alsop II dive into Meta's latest AI model releases and their broader…
Stewart SquaredEpisode #98: What Apple Gets That the Rest of Tech Doesn't: Trust Scales
In this episode of the Stewart Squared podcast, host Stewart Alsop sits down with his father, guest Stewart Alsop II, to tackle a wide range of tech topics…
Stewart SquaredEpisode #97: How AI Is Rewriting the Rules of Computing
Stewart Alsop sits down with his father, Stewart Alsop II, to unpack what chip design even means anymore, starting with OpenAI's Jalapeno chip and the wild…
Stewart SquaredEpisode #96: From Steve Jobs to AI: The Stories That Never Became Data
In this episode of Stewart Squared, Stewart Alsop III sits down with his father, Stewart Alsop II, for a wide-ranging conversation that moves from a heartfelt…
Stewart SquaredEpisode #95: Schrodinger's Bubble: Nobody's Keeping Up, And That's Okay
In this episode of the Stewart Squared podcast, host Stewart Alsop sits down with his father, guest Stewart Alsop II, to tackle corrections from last week's…
Stewart SquaredEpisode #94: ARM Wrestling: NVIDIA's Quiet Coup Against Intel
In this episode of the Stewart Squared podcast, host Stewart Alsop speaks with his father Stewart Alsop II, who joins from Tokyo while Stewart broadcasts from…
Stewart SquaredEpisode #93: Too Big to Question: SpaceX, Wall Street, and the End of Accountability
In this episode of the Stewart Squared podcast, host Stewart Alsop and guest Stewart Alsop II tackle the explosive SpaceX IPO, conflict of interest in politics…
Stewart SquaredEpisode #92: The $1.75 Trillion Bet: What WeWork Taught Us About the SpaceX IPO
On this episode of the Stewart Squared podcast, host Stewart Alsop speaks with his father Stewart Alsop II about the SpaceX IPO and whether such a massive…
Stewart SquaredEpisode #91: The $1.5 Trillion Question: Why SpaceX's IPO Math Doesn't Add Up
In this episode of the Stewart Squared podcast, host Stewart Alsop and his father Stewart Alsop II dig into the major AI and tech IPOs hitting the market, with…
Stewart SquaredEpisode #90: Nobody Knows What Software Is Worth Anymore
In this episode of the Stewart Squared podcast, host Stewart Alsop II connects from Tangier, Morocco while his son Stewart Alsop III digs deep into the…
Stewart SquaredEpisode #89: Vibe Engineer Meets Venture Capitalist: A Father-Son Dispute About the Future
In this episode of Stewart Squared, host Stewart Alsop sits down with his father, Stewart Alsop II, for a wide-ranging conversation that moves from the…
Stewart SquaredEpisode #88: Conspiracy Factist vs. Practical Capitalist: The Alsop Debate
In this episode of the Stewart Squared podcast, host Stewart Alsop III and his father Stewart Alsop II tackle the state of Silicon Valley, questioning whether…
Stewart SquaredEpisode #87: Tighter Than Microsoft, Smarter Than Apple: Anthropic's Blueprint to Own the AI Stack
In this episode of the Stewart Squared podcast, host Stewart Alsop is joined by his father, Stewart Alsop II, to talk through a wide range of topics stemming…
Stewart SquaredEpisode #86: The Orchestration Layer: One Indie Builder's War Against Platform Lock-In
In this episode of Stewart Squared, host Stewart Alsop sits down with his father, Stewart Alsop II, for a wide-ranging conversation that kicks off with…
Stewart SquaredEpisode #85: The Conspiracy Theory That Isn't: When Silicon Valley Quietly Changes the Deal
In this episode of Stewart Squared, host Stewart Alsop is joined by his father Stewart Alsop II to cover a wide range of topics sparked by a growing…
Stewart SquaredEpisode #84: From World Models to Robot Orchestras: Inside the New Stack of Real-Time Intelligence
This week on Stewart Squared, Stewart Alsop sits down with his father Stewart Alsop II — veteran tech journalist, former editor of InfoWorld, and longtime…
Stewart SquaredEpisode #83: The Focus Layer: Why Anthropic, NVIDIA, and Cloudflare Are Winning the Same War
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 a sharp…
Stewart SquaredEpisode #82: What Happens When You Stop Trusting Platforms and Start Building Your Own
Stewart Alsop is joined by his guest, Stewart Alsop II, for a wide-ranging conversation about the technology behind modern podcasting and streaming, starting…
Stewart SquaredEpisode #81: Indoor, Outdoor, In Between: The Real Future of Human Experience
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 Stewart's…
Stewart SquaredEpisode #80: The Unreal Engine of Everything: Betting on the Next Shift in Entertainment
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 sparked by…
Stewart SquaredEpisode #79: Inside the Collision: Where AI, Hollywood, and the US Government Are All Breaking at Once
In this episode of Stewart Squared, host Stewart Alsop III sits down with his father Stewart Alsop II — veteran tech journalist turned venture capitalist…
Stewart SquaredEpisode #78: The Vibe Coding Takeover: How Bot Swarms Are Turning SaaS Into an Endangered Species
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 Alsop II, who…
Stewart SquaredEpisode #77: The Napster Effect: Why the Old Guard Always Loses
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 media and…
Stewart SquaredEpisode #76: Dear Hollywood, Give Up: Lessons from Napster, Netflix, and the Inevitable
In this episode of the Stewart Squared podcast, host Stewart Alsop III speaks with his father Stewart Alsop II about the ongoing battle between Hollywood and…
Stewart SquaredEpisode #75: The Real-Time Problem: Why LLMs Hit a Wall and World Models Won't
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 world models…
Stewart SquaredEpisode #74: From Cold War to AI War: Navigating Power, Surveillance, and the Future of Democracy
In this episode of the Stewart Squared podcast, host Stewart Alsop sits down for a wide-ranging conversation that starts with insurance concepts but quickly…
Stewart SquaredEpisode #73: The Network Effect: How We Went from Manual Data Transfer to Global Information Warfare
In this wide-ranging episode of Stewart Squared, host Stewart Alsop sits down with his guest Stewart Alsop II to explore everything from the surprisingly…
Stewart SquaredEpisode #72: From Yahoo's Directory to Apple's Neural Chips: The Evolution of Structured Knowledge
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…
Stewart SquaredEpisode #71: The AI Momentum Trap: When Venture Models Replace Business Models
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…
Stewart SquaredEpisode #70: From Twitter to Threads: Escaping the Training Data Mines of Late Capitalism
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…
Stewart SquaredEpisode #69: From Floppy Disks to Claude Code: Riding the AI Dragon
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…
Stewart SquaredEpisode #68: Hot Tubs, Suits, and Silicon Souls: When Counterculture Built Computers
In this episode of Stewart Squared, hosts Stewart Alsop and Stewart Alsop II explore the fascinating connections between 1960s counterculture and the birth of…
Stewart SquaredEpisode #67: The Early Indicators: Will Google or OpenAI Dominate the Next Decade of AI?
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…
Stewart SquaredEpisode #66: The Randomness Engine: Why Silicon Valley Can't Be Cloned (And Why That Matters for AI)
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…
Stewart SquaredEpisode #65: From Strawberries to Silicon Valley: The Origin Story of Atari’s Mindset
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…
Stewart SquaredEpisode #64: The Last Mile of Intelligence: Real-Time Systems and Hardware Leap
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…
Stewart SquaredEpisode #63: From Mosaic to Gemini: The Evolution of How We Connect
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…
Stewart SquaredEpisode #62: From Cloudflare to Chaos: Mapping the Fault Lines of the AI Economy
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…
Stewart SquaredEpisode #61: Powering the Machine: Altman, Milei, and the Energy Behind AI’s Future
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…
Stewart SquaredEpisode #60: Manufacturing Intelligence: A Conversation on Apple, TSMC, and China’s Playbook
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…
Stewart SquaredEpisode #59: When Information Became the New Empire
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…
Stewart SquaredEpisode #58: Inventing Wonder: A Conversation with the Bushnells
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…
Stewart SquaredEpisode #57: Silicon, Sovereignty, and Speculation: The Stakes of AI’s Next Phase
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…
Stewart SquaredEpisode #56: The Internet’s Business Model Is Cracking..What Comes Next?
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…
Stewart SquaredEpisode #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…
Stewart SquaredEpisode #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…