Best Stewart Alsop III Podcasts (2025)

1
Episode #34: From Magellan to the Machine: Bill Gross on the Search for Meaning 1:01:49

2d ago1:01:49

1:01:49

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 o…

1
Episode #33: From Mainframes to Minds: Rethinking the Architecture of Intelligence 1:02:24

5d ago1:02:24

1:02:24

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 …

1
Episode #32: Startups, Deadlines, and Drift: The Venture Logic Behind Modern Newsrooms 52:31

14d ago52:31

52:31

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…

1
Episode #31: Satya’s Quiet Coup: How Microsoft Got Its Groove Back 51:12

21d ago51:12

51:12

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—ho…

1
Episode #30: From InfoWorld to x.com: The Patterns That Repeat 53:15

28d ago53:15

53:15

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 …

1
Episode #29: Bridging the Physical and Digital: Investing in the Next Big Shift 1:00:37

1M ago1:00:37

1:00:37

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 compu…

1
Episode #28: How to do world building? 57:26

1M ago57:26

57:26

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 b…

1
Episode #27: From Napster to OpenAI: The Relentless Disruption of Everything 40:11

2M ago40:11

40:11

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 emergi…

1
Episode #26: Steve Case on the Internet’s Wild Ride and What’s Next 57:24

2M ago57:24

57:24

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 ev…

1
Episode #25: The Third Convergence: When Reality and Digital Collide 53:41

2M ago53:41

53:41

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 co…

1
Episode #24: From Ethernet to AGI: Tracing the Threads of Connection 1:02:16

3M ago1:02:16

1:02:16

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 Ethern…

1
Episode #23: Big Tech, Big Government, and the Coming War Over Power 53:44

3M ago53:44

53:44

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., a…

1
Episode #22: Seeing the World Differently: Psychedelics, Media, and Modern Humanism 49:59

3M ago49:59

49:59

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 …

1
Episode #21: History on Repeat: Lessons from Electricity to AI 40:46

3M ago40:46

40:46

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 rev…

1
Episode #20: Old Giants vs. New Titans: SpaceX, Legacy Contractors, and the Cost of Progress 53:57

4M ago53:57

53:57

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 fosterin…

1
Episode #19: The DNA of Insight: Generational Lessons in Innovation and Communication 53:52

5M ago53:52

53:52

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 pub…

1
Episode #18: Why Innovation Needs Leadership: Stories from Silicon Valley and Beyond 48:37

5M ago48:37

48:37

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 wa…

1
Episode #17: From California to Buenos Aires: Gaming Bureaucracies in the Digital Age 47:50

5M ago47:50

47:50

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 Argent…

1
Episode #16: From TiVo to TikTok: TV Tech That Changed How We See the World 37:52

5M ago37:52

37:52

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…

1
Episode #15: Why Gen Z Thinks Differently: Growing Up in a World That Never Logs Off 38:16

6M ago38:16

38:16

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 is…

1
Episode #14: How We Got Here: A Journey Through Tech’s Defining Waves 38:31

6M ago38:31

38:31

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 cultura…

1
Episode #13: AI Hype vs. Reality: Cutting Through the Noise 48:47

6M ago48:47

48:47

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 ta…

1
Episode #12: The New Rules of Tech: From 90s Antitrust to Today’s AI Dilemma 1:01:07

6M ago1:01:07

1:01:07

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 mo…

1
Episode #11: The Internet’s Genesis: How the 1990s Opened the Floodgates of Innovation 38:52

7M ago38:52

38:52

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, discus…

1
Episode #10: Forty Years Later: Are We Finally There with AI? 43:10

7M ago43:10

43:10

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 adva…

1
Episode #9: The AI Whisperer: A New Era of Prompt-Based Programming 1:07:29

7M ago1:07:29

1:07:29

By Stewart Alsop II, Stewart Alsop III

1
Episode #8: The Rise of Personal Computing and the Fall of Trust 50:45

7M ago50:45

50:45

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 defe…

1
Episode #7: Satellites, Warfare, and the End of Terrestrial Tech 43:43

8M ago43:43

43:43

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 …

1
Episode #6: Evernet Dreams: The Intersection of Satellite Tech, Battery Innovation, and Constant Connectivity 45:29

8M ago45:29

45:29

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 por…

1
Episode #5: Silicon Valley's Dark Horse: Oracle’s Past, Present, and Future 43:10

8M ago43:10

43:10

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…

1
Episode #4: Building Giants and Guarding Integrity: Lessons from the Tech Trenches 48:32

8M ago48:32

48:32

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 a…

1
Episode #3: San Francisco: The Empire at Its Peak or on the Brink? 41:02

8M ago41:02

41:02

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 para…

1
Episode #2: The Evolution of Computing: a Generational Conversation 1:01:01

9M ago1:01:01

1:01:01

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 o…

1
Conferences: Why do people start them? 44:15

10M ago44:15

44:15

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 l…

1
Do the Hard Thing - How to Deal with Complexity, and Jerry Parker’s ETF 12:57

11M ago12:57

12:57

This episode NOTHING SAID ON THIS PODCAST IS INVESTMENT ADVICE.

1
Scripture, Philosophy, and Embracing Ambiguity with Zohar Atkins 37:26

1y ago37:26

37:26

Scripture, Philosophy, and Embracing Ambiguity with Zohar AtkinsSummary: In this episode of Courage Over Convention, we dive into a fascinating conversation with Zohar Atkins, a renowned scholar and founder of Etz Hasadeh. Join us in exploring how Judaism illuminates guiding truths even in this age of disruption. We discuss the impact of technology…

1
Juul Pods Ubiquitous While Psilocybin and Ketamine Therapy Are Broadly Illegal 33:56

1y ago33:56

33:56

One Juul pod contains as much nic as 20 cigs. “So yea you can sell em in a four pack right next to the gummy worms.”Psilocybin and ketamine therapy are the best treatment options for complex PTSD - predominantly suffered by victims of sexual assault. But bc these non-addictive substances can’t be effectively monetized, they are impossible for peopl…

1
Free Will: Worth Contemplating 1:15:48

1y ago1:15:48

1:15:48

A fun though perhaps controversial collaboration with Stewart Alsop III (host of the Crazy Wisdom Podcast). Subscribe to his podcast (Crazy Wisdom) - you’ll be glad you did. You can find him on Twitter @StewartalsopIIIYou can find me on Twitter @WoodyWiegmann(1) Woody's general perspective on free will, determinism, and the views of thought leaders…

1
Complex is Complicated, but Complicated ain’t Complex 15:39

1+ y ago15:39

15:39

Examining the oft-overlooked features of complexity that lead us to mistakenly approach intractable problems with immense hubris.

1
The Death of Nuance and Productive Iteration with Stewart Alsop III 26:38

1+ y ago26:38

26:38

In revisiting a past episode with Stewart, I realized I did not do justice to his excellent prompts. This is an edited episode, meant to offer more direct thoughts on the topics Stewart brought to the table. I did not edit Stewart’s contributions (they needed no adjustments) - only my own. Thus, this episode is not a representation of Stewart’s opi…

1
Secular Faith Structures: Part I 15:43

3y ago15:43

15:43

What do you do in a high-stakes game when the future is, by definition, entirely unpredictable?Shoutouts in this episode: Dr. Ben Hunt, Dunn Capital, Chesapeake Capital (Jerry Parker), Corey Hoffstein, Meb Faber, Rob Arnott, and Jess Bost!

1
Eliminating Large Portfolio Losses: Lessons from an Ancient Sage 17:32

3y ago17:32

17:32

Sun Tzu's teachings apply broadly - and they certainly apply to portfolio construction.

1
The Fed and Their Transi-Story 29:26

3y ago29:26

29:26

I promise not to try not to fuck with your mindPromise not to mind if you go your way and I go minePromise not to lie if I'm looking you straight in the eyePromise not to try not to let you down

1
A Crash is Coming - Will it be Merely Economic or Social (and then Economic)? 13:58

3y ago13:58

13:58

This is the first episode of a three or four-part series discussing the futility of seeking a balance between two powerful yet diametrically opposed American ideals. Without a miracle (which I discuss in the third episode), the strain on our societal fabric will continue to increase exponentially, until things are no longer tenable.…

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