Stewart Squared

In this episode of the Stewart Squared podcast, host Stewart Alsop and his son Stewart Alsop II explore the convergence of autonomous robotics, corporate consolidation, and network infrastructure. The conversation kicks off with speculation about a potential Tesla-SpaceX merger, drawing parallels to Japanese keiretsus and examining how Elon Musk might be building what they dub "Musk X"—a unified empire spanning rockets, AI, autonomous vehicles, and satellite networks. From there, they venture into the world of dog bots and robotic operating systems, with Stewart II demonstrating real-time AI-generated web content and discussing his plans to build mesh networks for da...

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 robotics, kicking off with Stewart III's upcoming hands-on experience with a four-legged dog robot running open-source software. The conversation ranges from the fragile state of current AI autonomy—distinguishing between truly autonomous systems and what are essentially sophisticated loops—to the practical challenges of implementing agents like Muse, Hermes, and Claude in daily life. They explore why industrial robots remain automated rather than autonomous, the security implications of Chinese hardware in American robo...

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 S-1 prospectus reached Reuters before the public could read it. Stewart Alsop II explains how confidential SEC filings work and why the company can't talk about the offering, and the two unpack the risk factors Reuters quoted: roughly 80 of 261 pages, including warnings of catastrophic or existential risk from self-preservation behavior, evaluation awareness and late-emerging capabilities, which Stewart believes is a first for any IPO. Stewart Alsop II draws a parallel between Anthropic's constitution...

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 and foundation models, with a particular focus on Anthropic's anticipated IPO. The conversation spans from Stewart's latest adventures in self-hosting and creating sizzle reels with AI to the seismic shift brought by Anthropic's release of Claude Opus 5.5—a model that's both cheaper and more capable, fundamentally changing the economics of AI services. The discussion takes a historical turn as they compare today's AI competition to past tech IPO races, from the 1986 cluster of...

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 seismic shifts happening in AI right now. The two dive into whether Anthropic will actually go public despite the existential risk narrative Dario Amodei has been pushing, exploring the real reasons these companies need to IPO (hint: it's about the cash burn). They discuss California's new AI regulations under Gavin Newsom, the emerging threat of JEV—a new AI architecture from a company called Hyde that could upend the entire foundation model business—and why...

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 development, moving beyond what Stewart calls the "absurd doomer narrative" that dominated headlines this week instead of Anthropic's anticipated S-1 filing. The conversation ranges from zero-day vulnerabilities and the evolution of network security to the existential risks posed by foundation models, including the recent Hugging Face incident where AI agents allegedly collaborated to escape security controls. The Alsops debate whether Anthropic's coordinated messaging around AI safety represents a sophisticated regulatory capture strategy aligned with Democratic...

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 AI landscape following the recent releases of OpenAI's Astra and Anthropic's Opus 5. The conversation explores how both models have reached a level where it's becoming difficult for even intelligent people to evaluate their capabilities, with OpenAI leaning heavily into visual computing and 3D graphics while Anthropic focuses on language and mathematics. The hosts examine the competitive dynamics between the two AI leaders, discussing Sam Altman's more disciplined approach following executive turnover and Dario Amodei's...

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 tech landscape. They compare it to SpaceX's recent public offering, examining how Anthropic's projected $30 trillion in potential revenue stacks up against current performance and whether the company can sustain its growth amid mounting customer frustration with usage limits and pricing. The conversation ranges from the mechanics of SPACs versus traditional IPOs (including their portfolio company Ursa Major's SPAC announcement), to dual-class share structures that give founders like Dario Amodei control similar to Zuckerberg...

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 happening across big tech, with Google raising $85 billion in equity and floating bonds to fund data centers while questions mount about whether this mirrors the dark fiber overbuilding of 2001. They analyze the diverging paths of Anthropic and OpenAI, with Anthropic's revenue reportedly hitting a $65 billion run rate—now surpassing OpenAI—while maintaining a focused enterprise strategy versus OpenAI's scattershot approach and slowing growth. The conversation covers everything from token economics and the commodification of frontier mode...

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, and growth equity have evolved—and possibly converged—since the 2008 financial crisis. They explore how massive liquidity injections in 2020 fueled a PE buying spree, why the distinctions between investment categories are blurring as everyone gets measured by the same metrics (DPI—distributions per investment), and whether the whole system is starting to break down. The conversation touches on everything from SPACs making a comeback to Elon Musk's SpaceX IPO, the financialization of restaurants, and ho...

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 and Waymo's expansion to Zoox's driverless design and NVIDIA's growing role as the go-to OEM partner for automakers building software- and AI-defined vehicles — before the conversation branches into dual-use tech lessons from Ukraine, the US-China race in autonomy and semiconductors, the DRAM memory shortage squeezing Apple and the gaming industry, Slate's stripped-down electric truck, and a closing riff on performance-based, subscription-driven podcasting.

Timestamps

00:00 — Self-driving cars and the fallout from Cruise’s collap...

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 Leopold Aschenbrenner's hedge fund and the memory chip shortage that's rippling through everything from Apple's product line to the gaming industry, before moving into how OpenAI and Sam Altman's data center spending is reshaping global compute demand, the widening gap between American and international tech ecosystems, China's uneasy relationship with open source AI, and a look at Mira Murati's new venture Thinking Machines Lab and its fine-tuning tool Tinker, wrapping up...

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 features that still don't quite work, before spiraling into Apple's org chart and headcount, the lost art of building apps, chip design and the Apple 100, open source versus closed source (MLX, the Linux kernel, GitHub vs. GitLab), Claude Code and why Anthropic's terminal-first approach might be winning the AI race, the commoditization debate around Chinese open source models, Adobe's fall from grace and the Postscript-to-Flash saga with Steve Jobs, real-time publishing and the Ben...

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 Apple's iOS 27 preview beta and the long road to Apple Intelligence, to the trust gap between Anthropic and OpenAI and the rise of digital-twin apps like Sentience, before pivoting into venture capital territory with a candid look at Andoril, Palmer Luckey, and the defense-tech boom reshaping how the primes do business; from there the two work through the surveillance creep of modern police tech, China's near-peer standing against the U.S. and its...

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 issues with user addiction, touching on the European Commission's warnings about addictive features and massive fines totaling $1.4 trillion from US state attorney generals. The conversation ranges from Meta's Meta Super Intelligence Lab and their attempts to catch up to OpenAI and Anthropic, to the impossibility of governments controlling AI development as countries rush to build sovereign models. They discuss NVIDIA's open source robotics models, debate the future of humanoid versus non-humanoid robots, and...

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 from AI chip design to cybersecurity vulnerabilities. The conversation covers OpenAI's Jalapeno chip (trained by AI in just nine months), the emerging etched.com platform, and Cloudflare's recent power move against Google, while Stewart shares his experience building real-time games on video calls and experimenting with ESP32 hardware for robotic projects. The discussion also dives into Meta's controversial KYC (know your customer) requirements that got Stewart kicked off Facebook and Instagram...

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 showrunner systems at TeamLab and Meow Wolf, autonomous vehicles and the LiDAR fight between Tesla and Waymo, Gaussian splats and world models, a detour into 3D printing and a failed IRL...

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 up close. The two also dig into Cold War history, Russia's ambiguous relationship with the West, the Alsop family's own journalism legacy, and how AI is reshaping the way we think about memory, personal data, and...

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 Stewart's increasingly frustrating relationship with what he calls an "abusive superintelligence." The conversation shifts to immersive art experiences as Stewart Alsop II reports from Japan, comparing his visit to TeamLab's digital projection exhibits with his investment...

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 from five years ago when they switched to their own ARM-based M-series and A-series chips. They discuss the competitive dynamics between chip manufacturers, the token apocalypse affecting AI coding assistants like Claude and Codex, and how companies like...

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 and Nancy Pelosi's husband's trades fall into the same category of insider dealing—though neither technically qualifies as illegal insider trading. From there, they dig into the mechanics of the SpaceX IPO, questioning how Elon Musk convinced major ba...

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 the company loses nearly $5 billion annually. The conversation ranges from the mechanics of IPOs and the SEC approval process to the only recent failed IPO (WeWork), SPACs versus traditional public offerings, the iron triangle of regulators and business interests...

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 Starlink, rocket launches, X (Twitter), and the struggling xAI/Grok business—with key researchers having already jumped ship after getting their SpaceX stock. The conversation covers Anthropic's explosive revenue growth (projecting $10 billion in Q2 alone) an...

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 consulting, examining why Silicon Valley has long held a visceral distrust of consultants while contractors thrive, and what AI-powered development means for how software gets built and sold in the coming years. Stewart III shares his journey from "vibe...

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 software, positioning it as a direct competitor to platforms like Riverside.fm and Squadcast. From there, they get into a business breakdown of OpenAI and Anthropic, debating whether Claude's recent stumbles are a blip or...

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 and the Technology Brothers Podcast Network (which was recently acquired by OpenAI). The conversation explores the friction between Stewart's millennial conspiracy-factist perspective and Stewart II's boomer practical capitalist viewpoint, covering everything from journalistic integrity and the...

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 broader discussion about Anthropic's business strategy versus OpenAI's, the Apple-versus-Microsoft analogy for how AI companies are positioning themselves, and why Dario Amodei keeps making bold claims about AGI while struggling to serve existing customers...

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 landscape between Anthropic, OpenAI, and Google's Gemini, touching on the OpenClaw orchestration framework controversy that got developer Peter Steinberger temporarily locked out, Anthropic's strategic positioning with its Mythos model, and the broader geopolitics of AI. They also...

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 loyalty. The two also get into the competitive dynamics between Apple, Google, and Anthropic in the LLM space, LinkedIn's "Browsergate" controversy, the role of IT departments in an AI-driven world, the RISC-V open-source instruction set...

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 they get into NVIDIA's push into CPUs, the difference between LLMs and world models, Waymo's autonomous driving stack, and what it actually feels like to orchestrate a swarm of AI coding agents while building four apps at o...

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, the conversation moves into the slowdown in AI model progress and the role of training data scarcity, the rise of vibe coding and AI-assisted software development, the architectural differences between CPUs and GPUs (with a nod to Jensen Hu...

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 points of presence, the role of Amazon S3 and AWS in storing and distributing media, and the differences between live streaming and recorded workflows. The discussion then moves into broader themes including distributed systems, server farms, GPUs versus CPUs in AI data...

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 show around the shift from traditional shopping malls to experience-based entertainment venues like Meow Wolf and the Sphere, the struggles facing movie theaters amid studio consolidation and streaming dominance, the rise...

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 Wolf, Netflix's acquisition of Warner Brothers, the Sphere in Las Vegas, and the future of movie theaters as digital distribution has replaced physical film reels. Stewart Alsop II shares insights from TK Media's investment thesis around...

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 Wolf and AREA15; Disney's choice of Josh D'Amaro as its new CEO; the collapse of Netflix's bid for Warner Bros. Discovery and what Ted Sarandos's White House visit may have signaled; Anthropic's very public standoff with...

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 murky security risks of autonomous bots and prompt injection, and what frameworks like OpenClaw mean for professional programmers versus curious amateurs. The two also wander — as is apparently th...

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 witnessing the revolutionary shift from lead typesetting to digital systems like CompuGraphic and Atex. The conversation traces the technological transformations that reshaped media—from the introduction of the Macintosh and PageMaker in the mid-1980s to the in...

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 that technology always wins in media—pointing to how this same pattern played out with Napster and the music industry. The conversation explores how the media landscape has shifted from broadcast television to cable to streaming, why Netflix's ma...

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 maxed out the LLM approach and needs to shift focus toward world models—a position championed by Yann LeCun. The conversation covers everything from the strategic missteps of Meta and the dominance of Go...

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 networks like Protect 612 in Minneapolis, and the challenges of intellectual property protection in the age of LLMs. Stewart Alsop II shares insights from his venture capital experience at NEA regarding patent processes and discusses various AI researchers' perspectives, particularly expressing alignment with Yann...