Stewart Squared

Welcome to the Stewart Squared podcast with the two Stewart Alsops! Today’s conversation intertwines the evolution of technology—from the rise of the PC and the internet to AI and space exploration—with the transformative power of psychedelics and their impact on media and creativity. From personal experiences with LSD to the cultural resonance of Meow Wolf and Burning Man, this episode unpacks ho...

Welcome to Stewart Squared podcast with the two Stewart Alsops! Today, we’re cruising along the Pacific Coast Highway with the ocean on one side and mountains on the other, diving into transformative moments in technology and society. From the electrification of homes in the late 19th century to the rise of AI and its parallels with those early revolutions, we explore how history shapes our unders...

Welcome to Stewart Squared podcast with the two Stewart Alsops! In this special episode, recorded on a scenic drive up the 101 from Los Angeles to Santa Barbara, the conversation explores a broad range of topics, from the evolution of Apple's iPhone as a "super tool" due to its unique hardware-software integration to Google's challenges in fostering innovation despite its moonshot projects. The St...

Welcome to the Stewart Squared podcast with the two Stewart Alsops! In this special episode, recorded while driving up the 101 from Los Angeles to Santa Barbara, the conversation flows from asteroid mining and manufacturing to a fascinating exploration of Apple's hardware-software integration, Google's competitive challenges, and the nuances of publishing in both traditional and modern contexts. T...

Welcome to Stewart Squared Podcast with the two Stewart Alsops! In this episode, the conversation spans decades of technological evolution, starting with the sci-fi-like introduction of personal computing, the transformative experience of using VisiCalc on an Apple II, and how tools like laser printers and browsers reshaped industries. Along the way, the Stewarts reflect on the revolutionary chang...

Welcome to Stewart Squared podcast with the two Stewart Alsops! This episode explores the fascinating concept of residency hacking, blending digital nomadism with innovative approaches to establishing legal residency in multiple jurisdictions. Stewart Alsop II discusses his transition from California to Buenos Aires, strategies for obtaining Argentinian residency and citizenship, and the unique ap...

Welcome to Stewart Squared podcast with the two Stewart Alsops. This episode takes listeners on a tour through television’s evolution, touching on the birth of broadcast TV and the monumental first “TV presidency” with JFK, which highlighted TV's influence on public perception. The Stewarts explore how the limited early broadcasts grew into cable’s 24/7 offerings, led by pioneers like CNN, and dis...

Welcome to the Stewart Squared podcast with the two Stewart Alsops! In today’s episode, the Stewarts dive into the rapid evolution of tech, from Apple's hearing aid integration in AirPods to Gen Z's unique relationship with social media and online authenticity. They discuss generational divides, especially how younger generations interpret world issues like the Israel-Palestine conflict differentl...

Welcome to Stewart Squared podcast with the two Stewart Alsops! This week’s episode takes you through decades of technological evolution, from Stewart Alsop II’s early experiences with personal computing and the internet boom to today’s era of AI and space exploration. They dive into how technology adoption has shaped our lives, discuss the cultural impacts of tools like VisiCalc and Mosaic, and e...

Welcome to Stewart Squared podcast with the two Stewart Alsops! In this episode, we tackle the evolution and current state of artificial intelligence, with Stewart Alsop II critiquing the hype surrounding generative AI and questioning its tangible benefits to individuals, while Stewart Alsop III discusses how AI is becoming an effective tool for tasks like coding and research. Together, they refle...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they dive into a fascinating discussion on the intersection of personal computing, federal agencies, and the transformative role of technology, both historically and in today's AI landscape. They explore the antitrust case of the 1990s, when Microsoft was accused of monopolistic practices, and connect it to modern par...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, Stewart Alsop III and his father, Stewart Alsop II, take a deep dive into the early days of the internet, technology trends, and the nature of predictions with "skin in the game." Stewart Alsop II, who was at the forefront of tech journalism and venture capital, discusses pivotal moments like the rise of personal comp...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore the trajectory of technology from the early days of personal computing to the current AI revolution. Topics include reflections on "The Last One" program from the 1980s, which promised to be the last program you'd ever need, and comparisons to today’s advancements with LLMs and platforms like Claude. The...

Welcome to the Stewart Squared podcast with the two Stewart Alsops, featuring special guest Joe Alsop. This episode covers the evolution of technology from the rise of personal computing to the current advancements in artificial intelligence. The discussion touches on the challenges of early programming, the progression of software development, and the revolutionary shift toward natural language p...

Welcome to Stewart Squared Podcast with the two Stewart Alsops. In this episode, they explore the early personal computing revolution, beginning with the rise of Lotus Notes and spreadsheets like VisiCalc, which transformed business forecasting and led to the dominance of software giants such as Microsoft. They discuss the ongoing influence of defense technologies, the development of artificial in...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, they explore pivotal moments in technology, starting with the personal computing revolution, the evolution of smartphones, and how AI is shaping our future. Stewart Alsop II reflects on abandoning his "constellation of devices" theory after realizing, during a fishing trip in Iceland, that using multiple gadgets only...

Welcome to Stewart Squared podcast with the two Stewart Alsops! In this episode, they dive into the history of personal computing, the evolution of the internet, and the development of mobile phone technology, all within the context of AI and the Evernet theory. They discuss the intriguing advancements in satellite technologies, like Starlink's portable internet solutions, and Apple's integration...

Welcome to the Stewart Squared podcast with the two Stewart Alsops. In this episode, the discussion takes a deep dive into the intriguing history and current ventures of Oracle, particularly focusing on its founder, Larry Ellison, and his relationship with tech giants like Steve Jobs. The conversation also touches on Oracle's involvement in AI, its cloud computing endeavors, and the larger context...

Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, we continue our exploration of fiduciary responsibility within the realms of venture capital and business management. The discussion touches on the inherent conflicts of interest that arise when balancing responsibilities to investors, companies, and stakeholders. We also reflect on how trust, integrity, and effective...

Welcome to the Stewart Squared podcast with the two Stewart Alsops! In this episode, Stewart Alsop II and Stewart Alsop III discuss the complexities of San Francisco’s tech scene, the future of AI, and the evolution of tech infrastructure. They explore how San Francisco’s self-perception contrasts with a broader sense of national decline, draw parallels between historical empires and modern societ...

Welcome to the Stewart Squared podcast with the two Stewart Alsops interviewing Joe Alsop who started Progress Software and took it all the way to IPO. In this episode, we explore the fascinating history of the early personal computing industry, sharing insights and anecdotes from Joe's extensive career, including his time at MIT and the founding of Progress Software. We discuss the evolution from...

In this episode of Crazy Wisdom's special series, Stewart Squared, Stewart Alsop III and his father Stewart Alsop II delve into various topics. They discuss the fragmented theme of AI, AI wearables, and technology conferences, including anecdotes and the purpose behind such events. They explore the evolution of tech products, mentioning companies like Apple and Google and their approaches to produ...