Stewart Squared cover art

All Episodes

Stewart Squared — 99 episodes

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Title
1

Episode #99: Can Money Buy Meta a Comeback in AI?

2

Episode #98: What Apple Gets That the Rest of Tech Doesn't: Trust Scales

3

Episode #97: How AI Is Rewriting the Rules of Computing

4

Episode #96: From Steve Jobs to AI: The Stories That Never Became Data

5

Episode #95: Schrodinger's Bubble: Nobody's Keeping Up, And That's Okay

6

Episode #94: ARM Wrestling: NVIDIA's Quiet Coup Against Intel

7

Episode #93: Too Big to Question: SpaceX, Wall Street, and the End of Accountability

8

Episode #92: The $1.75 Trillion Bet: What WeWork Taught Us About the SpaceX IPO

9

Episode #91: The $1.5 Trillion Question: Why SpaceX's IPO Math Doesn't Add Up

10

Episode #90: Nobody Knows What Software Is Worth Anymore

11

Episode #89: Vibe Engineer Meets Venture Capitalist: A Father-Son Dispute About the Future

12

Episode #88: Conspiracy Factist vs. Practical Capitalist: The Alsop Debate

13

Episode #87: Tighter Than Microsoft, Smarter Than Apple: Anthropic's Blueprint to Own the AI Stack

14

Episode #86: The Orchestration Layer: One Indie Builder's War Against Platform Lock-In

15

Episode #85: The Conspiracy Theory That Isn't: When Silicon Valley Quietly Changes the Deal

16

Episode #84: From World Models to Robot Orchestras: Inside the New Stack of Real-Time Intelligence

17

Episode #83: The Focus Layer: Why Anthropic, NVIDIA, and Cloudflare Are Winning the Same War

18

Episode #82: What Happens When You Stop Trusting Platforms and Start Building Your Own

19

Episode #81: Indoor, Outdoor, In Between: The Real Future of Human Experience

20

Episode #80: The Unreal Engine of Everything: Betting on the Next Shift in Entertainment

21

Episode #79: Inside the Collision: Where AI, Hollywood, and the US Government Are All Breaking at Once

22

Episode #78: The Vibe Coding Takeover: How Bot Swarms Are Turning SaaS Into an Endangered Species

23

Episode #77: The Napster Effect: Why the Old Guard Always Loses

24

Episode #76: Dear Hollywood, Give Up: Lessons from Napster, Netflix, and the Inevitable

25

Episode #75: The Real-Time Problem: Why LLMs Hit a Wall and World Models Won't

26

Episode #74: From Cold War to AI War: Navigating Power, Surveillance, and the Future of Democracy

27

Episode #73: The Network Effect: How We Went from Manual Data Transfer to Global Information Warfare

28

Episode #72: From Yahoo's Directory to Apple's Neural Chips: The Evolution of Structured Knowledge

29

Episode #71: The AI Momentum Trap: When Venture Models Replace Business Models

30

Episode #70: From Twitter to Threads: Escaping the Training Data Mines of Late Capitalism

31

Episode #69: From Floppy Disks to Claude Code: Riding the AI Dragon

32

Episode #68: Hot Tubs, Suits, and Silicon Souls: When Counterculture Built Computers

33

Episode #67: The Early Indicators: Will Google or OpenAI Dominate the Next Decade of AI?

34

Episode #66: The Randomness Engine: Why Silicon Valley Can't Be Cloned (And Why That Matters for AI)

35

Episode #65: From Strawberries to Silicon Valley: The Origin Story of Atari’s Mindset

36

Episode #64: The Last Mile of Intelligence: Real-Time Systems and Hardware Leap

37

Episode #63: From Mosaic to Gemini: The Evolution of How We Connect

38

Episode #62: From Cloudflare to Chaos: Mapping the Fault Lines of the AI Economy

39

Episode #61: Powering the Machine: Altman, Milei, and the Energy Behind AI’s Future

40

Episode #60: Manufacturing Intelligence: A Conversation on Apple, TSMC, and China’s Playbook

41

Episode #59: When Information Became the New Empire

42

Episode #58: Inventing Wonder: A Conversation with the Bushnells

43

Episode #57: Silicon, Sovereignty, and Speculation: The Stakes of AI’s Next Phase

44

Episode #56: The Internet’s Business Model Is Cracking..What Comes Next?

45

Episode #55: From Justin.tv to Claude Hacks: Lessons in Tech, Money, and Security

46

Episode #54: Preference Stacks, Power Games, and the Future of War

47

Episode #53: Cycles of Scaling: How AI and Politics Break Systems

48

Episode #52: The Illusion of Choice in Big Tech

49

Episode #51: Ray-Bans, Apple Stock, and the Long Game of Power and Timing

50

Episode #50: Star Hubs, Server Farms, and the Strange New Geography of AI

51

Episode #49: The Next Internet Is Immersive Experience

52

Episode #48: The Slow Death of Social Media (And What Comes Next)

53

Episode #47: The Cost of Knowing Everything

54

Episode #46: Bubble Logic: Why AGI and Drones Feel Inevitable

55

Episode #45: Natural Language as the New Operating System

56

Episode #44: Consultants Preach, AI Learns, and CEOs Fall Behind

57

Episode #43: Meme Coins and Moon Mines: Surveillance in the Age of Trump and Musk

58

Episode #42: The Myth of Openness in a Dualistic Valley

59

Episode #41: Homebrew Aftershocks: Echoes from the Pre-Platform Era

60

Episode #40: Probabilistic Machines: Living with the Illusion of Control

61

Episode #39: Trust Issues: From Meme Coins to Mainframes

62

Episode #38: From IBM to AI: How Business Lost Its Mind and Found the Algorithm

63

Episode #37: Elegance vs. Exquisite: Rethinking Systems Old and New

64

Episode #36: Tiny Computers, Massive Shifts: The iPhone’s Quiet Coup

65

Episode #35: From the Great Society to the Great Fragmentation

66

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

67

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

68

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

69

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

70

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

71

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

72

Episode #28: How to do world building?

73

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

74

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

75

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

76

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

77

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

78

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

79

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

80

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

81

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

82

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

83

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

84

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

85

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

86

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

87

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

88

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

89

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

90

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

91

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

92

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

93

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

94

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

95

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

96

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

97

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

98

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

99

Conferences: Why do people start them?