Stewart Squared

In this episode of Crazy Wisdom, I, Stewart Alsop III, talk with my father, Stewart Alsop II, about the surprising reception of ChatGPT, the role of AI as a modern chaos agent, and the ways disruptive forces echo both in technology and politics. Our conversation weaves through corporate rivalries, the scaling challenges that shape giants of industry, and the geopolitical pressures facing nations like Argentina and Brazil under the IMF. We also draw on history—from Rome and the Iroquois to the early internet and the Telecommunications Act—to explore cycles of rise and decline, before turning to the personal dimension of how we form emotional attachments to AI and the need for cognitive armor in adapting to new technology.

Check out this GPT we trained on the conversation

Timestamps

00:00 The Alsops begin with the underwhelming reception of ChatGPT, noting how expectations clashed with everyday use.
00:05 They frame AI as a chaos agent, comparing its disruptive role to Trump in politics and how systems respond to disruption.
00:10 Corporate rivalries take center stage, exploring scaling challenges and the fragility of tech giants.
00:15 Attention shifts to Argentina, Brazil, and Iceland as examples of nations wrestling with IMF pressure and global finance.
00:20 They draw historical parallels to Rome and the Iroquois, examining federalism, cooperation, and inevitable cycles of decline.
00:25 The internet of the 1990s comes up, with the Telecommunications Act and Section 230 shaping today’s digital landscape.
00:30 The conversation turns personal, discussing emotional attachment to AI, the idea of cognitive armor, and the need for resilience in technology adoption.

Key Insights
  1. Stewart Alsop begins by pointing out how the arrival of ChatGPT was both overwhelming and underwhelming at the same time. People expected a science fiction breakthrough, but the reality was a tool that seemed limited until you really worked with it. That mismatch between expectation and practice is central to understanding how humans adapt to new technologies.
  2. A strong metaphor runs through the conversation: AI as a chaos agent, much like Trump in politics. Both disrupt predictable systems and expose fragility in the structures we rely on. Stewart emphasizes that chaos is not always destructive—it can be generative, forcing reorganization and adaptation in unexpected ways.
  3. When discussing corporate rivalries, the guest and Stewart trace how scaling is both the dream and the downfall of big companies. Success creates its own inertia, and this mirrors how technology itself often outpaces the organizations that try to contain it. The conversation highlights that size brings vulnerability as much as it brings power.
  4. Geopolitics is explored through Argentina, Iceland, Brazil, China, and Russia in relation to the IMF. These cases serve as reminders that nations, like companies, exist in webs of dependency and negotiation. Financial institutions can both stabilize and destabilize, much like algorithms can both structure and unsettle our digital lives.
  5. Stewart draws historical parallels to Rome and the Iroquois, noting that both federal systems and empires rise through cooperation but eventually strain under the weight of their own success. The insight is that cycles of rise and decline are built into human organization, no matter how advanced the tools or governance.
  6. The internet of the 1990s surfaces as a key precedent, where the Telecommunications Act and Section 230 created the framework for today’s platforms. This legislative scaffolding made the early internet a chaotic but fertile ground, and Stewart suggests AI is at a similar moment of possibility and risk.
  7. The discussion closes on the deeply personal dimension of technology, with Stewart Alsop III and his father reflecting on the emotional pull of AI. They emphasize the idea of “cognitive armor” as a way to protect ourselves from over-identifying with machines, recognizing that while AI mirrors human thought, it does not replace human judgment. For them, the challenge of technology adoption lies not just in mastering the tool, but in learning how to remain grounded and human while living alongside it.

What is Stewart Squared?

Stewart Alsop III reviews a broad range of topics with his father Stewart Alsop II, who started his career in the personal computer industry and is still actively involved in investing in startup technology companies. Stewart Alsop III is fascinated by what his father was doing as SAIII was growing up in the Golden Age of Silicon Valley. Topics include:

- How the personal computing revolution led to the internet, which led to the mobile revolution
- Now we are covering the future of the internet and computing
- How AI ties the personal computer, the smartphone and the internet together