Stewart Squared

Stewart Squared

Stewart Alsop II, Stewart Alsop III

Episodes 93
Avg. Duration 52m
Activity Highly Active
Since Jul 2024
Latest Episode Jun 2026

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Schedule
Weekly
Format
Episodic
Consistency
100%
Hosting
feeds.transistor.fm

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About This Podcast

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 internet and computing - How AI ties the personal computer, the smartphone and the internet together

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Recent Episodes

Episode #93: Too Big to Question: SpaceX, Wall Street, and the End of Accountability

Jun 11, 2026 53m

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 and finance, and whether we're heading…

Episode #92: The $1.75 Trillion Bet: What WeWork Taught Us About the SpaceX IPO

Jun 04, 2026 24m

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 public offering could actually fail. Stewart…

Episode #91: The $1.5 Trillion Question: Why SpaceX's IPO Math Doesn't Add Up

May 28, 2026 46m

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 SpaceX leading the charge at a…

Episode #90: Nobody Knows What Software Is Worth Anymore

May 21, 2026 52m

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 technical challenges of building video…

Episode #89: Vibe Engineer Meets Venture Capitalist: A Father-Son Dispute About the Future

May 14, 2026 1h 7m

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 technical to the historical to the financial.…

Episode #88: Conspiracy Factist vs. Practical Capitalist: The Alsop Debate

May 07, 2026 54m

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 it's been captured by corporate…

Episode #87: Tighter Than Microsoft, Smarter Than Apple: Anthropic's Blueprint to Own the AI Stack

Apr 30, 2026 1h

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 from their shared obsession with AI and…

Episode #86: The Orchestration Layer: One Indie Builder's War Against Platform Lock-In

Apr 23, 2026 55m

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's frustrations around Anthropic's…

Episode #85: The Conspiracy Theory That Isn't: When Silicon Valley Quietly Changes the Deal

Apr 16, 2026 54m

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 frustration with Anthropic's recent changes to…

Episode #84: From World Models to Robot Orchestras: Inside the New Stack of Real-Time Intelligence

Apr 09, 2026 50m

This week on Stewart Squared, Stewart Alsop sits down with his father Stewart Alsop II — veteran tech journalist, former editor of InfoWorld, and longtime Silicon Valley venture capitalist — for a…

Episode #83: The Focus Layer: Why Anthropic, NVIDIA, and Cloudflare Are Winning the Same War

Apr 02, 2026 51m

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 critique of OpenAI's lack of strategic…

Episode #82: What Happens When You Stop Trusting Platforms and Start Building Your Own

Mar 26, 2026 59m

Stewart Alsop is joined by his guest, Stewart Alsop II, for a wide-ranging conversation about the technology behind modern podcasting and streaming, starting with Riverside’s local recording approach…

Episode #81: Indoor, Outdoor, In Between: The Real Future of Human Experience

Mar 19, 2026 51m

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 recent trip to Tucuman, Argentina for a…

Episode #80: The Unreal Engine of Everything: Betting on the Next Shift in Entertainment

Mar 12, 2026 58m

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's recent fishing trip to Tierra…

Episode #79: Inside the Collision: Where AI, Hollywood, and the US Government Are All Breaking at Once

Mar 05, 2026 50m

In this episode of Stewart Squared, host Stewart Alsop III sits down with his father Stewart Alsop II — veteran tech journalist turned venture capitalist, co-founder of Alsop Louie Partners, and…

Episode #78: The Vibe Coding Takeover: How Bot Swarms Are Turning SaaS Into an Endangered Species

Feb 26, 2026 54m

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 puts him in the hot seat for a…

Episode #77: The Napster Effect: Why the Old Guard Always Loses

Feb 19, 2026 57m

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 how technology has continuously disrupted…

Episode #76: Dear Hollywood, Give Up: Lessons from Napster, Netflix, and the Inevitable

Feb 12, 2026 1h 5m

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 Silicon Valley, focusing on the Warner…

Episode #75: The Real-Time Problem: Why LLMs Hit a Wall and World Models Won't

Feb 05, 2026 54m

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 and their potential to eclipse large…

Episode #74: From Cold War to AI War: Navigating Power, Surveillance, and the Future of Democracy

Jan 29, 2026 1h 8m

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 expands into discussions about…

Frequently Asked Questions

How many episodes does Stewart Squared have?

Stewart Squared has published 93 episodes since July 2024, covering topics in Business, Entrepreneurship.

Is Stewart Squared still active?

Stewart Squared is currently highly active with new episodes weekly. Average episode length is 52m.

How do I contact Stewart Squared for sponsorship or guest appearances?

Sign up on Grep.FM to access contact details for Stewart Squared, including email and social media links.

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