Stewart Squared

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they navigate a sprawling conversation that begins with the unruly complexity of the modern browser and spirals into deeper territory—from Google’s jealous leap into the browser wars with Chrome, to the philosophical implications of Neuralink and the idea of owning one’s own data and mind. Stewart Alsop interviews his...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore the OpenAI–Microsoft partnership through the lens of historic “stupid agreements” in tech, starting with Software Arts and VisiCorp’s flawed VisiCalc deal. The conversation traces the evolution of tech bubbles from the early software industry to today’s AI hype, questioning whether artificial general inte...

Welcome to Stewart Squared podcast with the two Stewart Alsops, where they explore the evolution of software from 1.0’s “magical incantations” to 3.0’s natural language interfaces, discuss operating systems and their hardware roots, and unpack the significance of vertical integration exemplified by Apple’s silicon and software unification. This episode touches on large language models as cognitive...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore why consultants often fail in the tech world, how leadership skills are (or aren’t) taught in business schools, and the historical tension between technical and non-technical CEOs. They trace the evolution of Silicon Valley’s culture, from the idealistic hackers of the PC revolution to Amazon’s strategic...

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 early days of Internet telephony via Netscape and InSoft, but quickly spiral into the present, grappling with the geopolitical consequences of space-based surveillance, the moral bankruptcy of Trump’s crypto antics, and the disturbing creep of domes...

Welcome to Stewart Squared podcast with the two Stewart Alsops. This episode navigates the arc of the Internet’s transformation from the promise of an open network to the reign of closed platforms, tracing roots from AOL to mobile Facebook. The Stewarts debate algorithmic influence on user agency, reflect on early computing culture through anecdotes about VisiCalc and orthogonality, and critique t...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, father and son trace the tectonic shifts that shaped Silicon Valley—from the amateur hardware tinkerers at the Homebrew Computer Club to the institutional rise of venture capital and its entanglement with military-industrial imperatives. They explore how Boston, Texas, and even Johannesburg played pivotal but ultimate...

Welcome to Stewart Squared podcast with the two Stewart Alsops, where this episode takes you on a ride through vibe coding experiments, AI-powered doom loops, and the fading utility of language learning apps like Duolingo in a world of real-time translation glasses. Stewart Alsop shares how he replaced Descript with Claude-generated code, while Stewart II unpacks the uncanny valley between needing...

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, and whether it can be rebuilt. We go from the 1990s paranoia about driver’s licenses to today’s AI-powered pendants that record everything, from the erosion of open internet ideals to the rise of app store monopolies. We compare Apple’s branding collap...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they track the transformation of business from the IBM-dominated 1980s to today's AI-driven landscape, exploring how personal computing, the rise of the internet, and eventually search and social media changed the way companies operate. The conversation moves from early account control tactics to the disruptive power...

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. We journeyed through Gilman's incredible career, from pioneering video games in the 80s with severe hardware limitations and the whirlwind of the Pokemon card craze, to his instrumental work founding In-Q-Tel for the CIA and the eventual creation of...

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 struggling personal computer company to the launch of the iPhone, marking a deeper convergence of mobile technology and cloud infrastructure. The Stewarts explore how the so-called "Web 2.0" years—deceptively quiet between the dot-com crash and the s...

Welcome to Stewart Squared podcast with the two Stewart Alsops. Today’s episode moves beyond technology to explore a deeply personal and historical reflection on the Great Society under Lyndon B. Johnson, sparked by a late-night email about the political and cultural shifts of the 1960s. The conversation weaves together vivid childhood memories of JFK’s inauguration and assassination, the dramatic...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this wide-ranging conversation, they’re joined by legendary entrepreneur and Idealab founder Bill Gross to trace the arcs of personal computing, the early Internet, and today's AI boom. The episode explores Bill’s early work with products like Lotus Magellan and GoTo.com, reflects on how foundational technologies transformed from n...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation starts with a personal quest into vector databases and linked data, but opens into a sweeping narrative of how the Internet—built on protocols like TCP/IP and scaffolding like URIs—evolved from Cold War military infrastructure into the backbone of our digital civilization. The Stewarts revisit the int...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation weaves through the evolution of media, venture capital’s long shadow over technology, and how editorial instincts have (or haven’t) adapted to the pace of software. Stewart Alsop II brings firsthand insight into the early days of digital publishing and the structural mismatches that still shape newsro...

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 Microsoft’s culture, capital strategy, and role in the AI boom. The conversation traces the company’s shift from a Windows-obsessed, top-down org to a more open, developer-friendly platform player—how Nadella’s quiet power differs from the bombast o...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation winds through a rich mix of personal history, editorial philosophy, and the evolution of tech—from getting fired (twice) to putting Steve Jobs on the cover of Inc. in 1981, from the impact of VisiCalc on Apple II adoption to the deeper meaning of what it means to be an editor. Alongside reflections on...

Welcome to Stewart Squared podcast with the two Stewart Alsops, featuring special guest Jim Ward. In this episode, Jim shares insights on the "third convergence" and the "reality disturbance," exploring how emerging technologies like AI, XR, and immersive media are reshaping our world. He and Stewart Alsop II discuss the evolution of personal computing, the internet, and mobile technology, drawing...

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, internet, and mobile phone to the current state of AI, cutting through the hype with firsthand insights from decades of industry experience. They discuss concepts like "reality disturbance," introduced by Jim Ward, and the "third convergence," which tie...

Welcome to the Stewart Squared podcast with the two Stewart Alsops. In this episode, we explore the concept of "convergences" in technology, focusing on the rise of personal computing, the internet, and smartphones. We revisit Nicholas Negroponte’s insights on digital publishing, the second convergence's shift to networked computing, and the emerging "reality disturbance"—where digital and real-wo...

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 this episode, we cover his journey from early internet days to building AOL, the role of venture capital beyond traditional tech hubs, and how policy shapes innovation. Steve also shares insights on the evolution of AI, the challenges of partnerships, and...

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 to 2045 where the digital and physical worlds become indistinguishable, creating what Stewart Alsop Jr. calls the "reality disturbance field". Building on the First Convergence (the rise of personal computing and digital media) and the Second Converge...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, we explore the evolution of networking—from the early days of isolated personal computers to the transformative rise of local and wide area networks, and the eventual dominance of the internet. The discussion covers key milestones like Bob Metcalf’s invention of Ethernet, the emergence of TCP/IP protocols, and the piv...

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 the shifting political landscape, the role of populism, and whether America is undergoing a fundamental realignment. We explore Trump’s influence, the rise of figures like Javier Milei and RFK Jr., and the ongoing battle between entrenched bureaucra...