Stewart Squared

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 claim that it was designed in nine months using their own LLM. They trace the CPU from its personal computer origins through GPUs, FPGAs, and the strange new world where anyone might vibe code a chip, then swing into digital projection and show...

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 tribute to the late Brent Schlender — legendary tech journalist and author of Becoming Steve Jobs — through the history and philosophy of journalism, the concept of the fourth estate, and what it meant to cover Silicon Valley's biggest names...

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 show before diving into the rapid pace of AI development and whether anyone can truly keep up. They explore Brian Chesky's new AI lab venture, Anthropic's controversial Fable release and subsequent restrictions by the US government, and Stewar...

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 Buenos Aires at 5 AM his time. The conversation covers NVIDIA's new Spark chip announcement and its partnership with Microsoft to bring ARM-based processors to Windows PCs, finally allowing Windows to compete with Apple's performance gains f...

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 toward economic collapse or the singularity. The conversation kicks off with them acknowledging they had to restart recording after getting into a heated argument about whether Trump's stock trading an...

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 Alsop II published his analysis just fifteen minutes before recording at sallsop.substack.com, questioning the logic behind the $1.75 trillion valuation and $75 billion raise, especially given that th...

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 controversial $1.5 trillion valuation despite just $20 billion in revenue. They break down how SpaceX's massive S-1 filing (so big it crashed Claude's context window) reveals a company now bundling together St...

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 conferencing software, specifically tackling the notorious lip sync problem that's consumed his last two months. The conversation moves from mutation testing and DevOps to exploring the future of software cons...

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. The two kick things off with Stewart's self-proclaimed evolution from "vibe coder" to "vibe engineer," as he tackles the tricky challenge of audio and visual sync in his own custom podcast recording sof...

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 interests and discussing how they can maintain an independent voice in technology commentary. Stewart presents a manifesto for building the show in public while avoiding the pitfalls of podcasts like All In an...

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 technology. The conversation kicks off with Stewart's frustrations around recent changes to Claude that have disrupted his morning workflow of building his own coding and planning agents, leading into a...

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 shifting subscription and API access policies for Claude, including the jump to a $200/month plan and what he sees as a quiet degradation in service quality. From there, the two cover the competitive landsc...

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 their subscription model, which leads into a broader conversation about trust in Silicon Valley and the historical patterns of companies like Microsoft, Meta, and OpenAI either earning or burning customer...

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 wide-ranging conversation that moves from the origins of the CPU and operating systems all the way to the geopolitical chip war playing out between ARM, Intel, RISC-V, and China's SMIC. Along the way the...

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 focus under Sam Altman and how that compares to Anthropic's disciplined, consistent approach — including Anthropic's explosive ARR growth from $14 billion to $19 billion in just three months. From there,...

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 and expanding into WebRTC, live streaming challenges, content delivery networks, and the evolution from Akamai to today’s cloud infrastructure. They discuss how Twitch scaled with custom servers and p...

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 wedding, which sparked observations about how malls and social culture in Argentina and Brazil still resemble the American experience of the 1990s. From there, the two dig into the broader thesis of the...

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 del Fuego, Argentina, including a brief tangent on Starlink satellite coverage in the Southern Hemisphere. The conversation moves into the evolving world of immersive entertainment, touching on Meow Wo...

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 early investor in both Twitch and Meow Wolf — to cover a wide-ranging set of topics including the future of immersive entertainment and whether the mall concept is due for a creative reinvention à la Meow...

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 wide-ranging conversation about the state of AI and software development. The elder Alsop leads the charge through topics including the rise of vibe coding, the threat AI agents pose to the SaaS industry, the...

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 the publishing industry. Stewart Alsop II recounts his early experiences with hot type printing at Groton in the 1960s, working at the Pasadena Guardian after graduating college in 1975, and witnessin...

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 Brothers Discovery saga involving potential buyers Netflix and Paramount (backed by tech investor David Ellison). Stewart Alsop II argues that Hollywood needs to stop "clutching their pearls" and accept...

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 language models as the future of AI development. Stewart II shares insights from his newsletter "What Matters? (to me)" available at salsop.substack.com , where he argues that the industry has already ma...

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 geopolitical systems, AI development, and patent law. The conversation covers the breakdown of the post-Reagan world order, the rise of surveillance technology through organizations like ICE, citizen intelligence...

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 complex world of 1980s data transfer—when moving files from a Commodore to a Mac required physical cables and serious technical know-how—to how AI is revolutionizing venture capital deal-making and legal negotiations. The conversation weaves thro...