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 the rise of AI devices like the Limitless pendant—linking it to Sam Altman's tangled investment trail and speculative visions of screenless tech. Their dialogue touches on Silicon Valley's philosophical shift—from engineering pragmatism to fantastical thinking—and asks whether companies like Google and Apple have the institutional structures to evolve meaningfully in the AI era.

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Timestamps

00:00 – Discussion opens on the walled garden concept, contrasting early open Internet ideals with Facebook and AOL's closed models.
05:00 – Shift to Facebook mobile and how the app's design deepened platform control, suppressing outbound links via algorithmic downgrading.
10:00 – Exploration of what algorithms are, including foundational insights from VisiCalc and orthogonal programming logic.
15:00 – Critique of fantastical thinking in Silicon Valley: effective altruism, Singularity, and AI determinism vs. randomness.
20:00 – Deep dive into AI devices, focusing on the Limitless Pendant, its usability issues, and Sam Altman's conflicted role as early investor.
25:00 – Speculation on hardware innovation, Raspberry Pi and Arduino, and ethical concerns around investing in competitors.
30:00 – Analysis of Google’s product culture, its failure in product management, and DeepMind's limited integration.
35:00 – Reflection on monopolistic behavior, moonshot divisions, and overfunding as a source of magical thinking.
40:00 – Final thoughts on institutional IT, comparing Apple, Netflix, and Chinese firms like Huawei in real-time software integration.

Key Insights

1. The Internet's Evolution into Walled Gardens: The Stewarts reflect on the shift from an open, user-driven Internet to a closed ecosystem dominated by platforms like Facebook and Twitter. While early services like AOL were walled gardens, there was a middle era of openness with the rise of the web. The arrival of mobile apps—especially Facebook's mobile transition—cemented a new kind of user lock-in, where links out are suppressed and attention is algorithmically contained.
2. Mobile as the Turning Point: The transition of Facebook to mobile marked a pivotal shift. Initially resistant to app development because of its open web ethos, Facebook eventually embraced mobile, realizing it granted total control over the user experience. This catalyzed the modern model of platform dominance, where linking out is discouraged and algorithmic prioritization curates user attention.
3. Algorithm Awareness and Cultural Impact: The rise of social media brought public awareness of algorithms as tools that influence behavior and visibility. What was once a backend concept known only to programmers became part of everyday language. The Stewarts trace this shift to platforms like Instagram and Facebook, which made algorithmic curation central to user experience and discourse.
4. AI Devices and the Limitless Pendant: Stewart II reviews the Limitless pendant, a wearable AI device that records conversations and summarizes them, calling it a “peek into the future” with usability flaws. The device’s origins as Rewind AI and its investment from Sam Altman raise ethical questions, especially now that Altman is backing potentially competing ventures like Jony Ive’s AI projects.
5. Magical Thinking in Silicon Valley: The episode critiques Silicon Valley’s drift from engineering rigor to speculative idealism—highlighting effective altruism, singularity thinking, and techno-utopian visions. They note how once-practical cultures are now marked by dualisms: doomer vs. accelerationist, utopian vs. dystopian, with little room for nuanced middle grounds.
6. China’s Role in Tech Innovation: Huawei’s expansion into cars prompts a reflection on whether Chinese firms’ multi-domain innovation reflects cultural differences. The Stewarts ponder whether China’s success is driven by collective orientation or state direction, and what it implies for U.S. competitiveness in hardware and manufacturing.
7. Institutional Knowledge and IT Competence: The episode closes on the importance of institutional IT knowledge, citing Apple and Netflix as companies that deeply understand their operational infrastructure. This understanding, they argue, enables better product development and company coherence—unlike firms that spray money across moonshots without disciplined management.