Welcome to Stewart Squared podcast with the two Stewart Alsops. In this episode, the conversation ranges across the years that saw Apple shift from a struggling personal computer company to the launch of the iPhone, marking a deeper convergence of mobile technology and cloud infrastructure. The Stewarts explore how the so-called "Web 2.0" years—deceptively quiet between the dot-com crash and the smartphone boom—were in fact the foundation for the modern Internet, with fiber laid during the crash powering today's broadband-dependent innovations. From Apple's cautious approach to third-party apps to the implications of subscription economics born partly out of mobile gaming and cloud SaaS, the discussion weaves technical detail with personal anecdotes—like a missed investment opportunity in Elon Musk's x.com, or the early struggles and eventual transformation of Justin.tv into Twitch. For listeners curious about Apple's trajectory post-Steve Jobs, Stewart Alsop II references a relevant article, “Dear Tim Cook, Maybe You Should Consider Retiring”.

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Timestamps

00:00 Apple’s transition from personal computers to the iPhone, Web 2.0’s rise, and early broadband limitations.
05:00 The iPhone as a pocket computer, initial app limitations, and the creation of the App Store pushed by Scott Forstall.
10:00 Investing dynamics of the early 2000s, the dot-com crash aftermath, and a missed opportunity with Elon Musk’s x.com.
15:00 AI comparisons to past tech waves, cloud computing’s economics, and the rise of the subscription model.
20:00 Claude as a developer’s tool, DIY infrastructure, and the economics of replacing SaaS like Descript.
25:00 The emergence of the cloud via AWS, SaaS adoption, and enterprise migration toward 40% cloud usage.
30:00 Infrastructure’s silent buildup during the bust years, fiber-optic backbones, and Tim O'Reilly’s Web 2.0 framing.
35:00 Investment in Justin.tv, the origin of Twitch, and early challenges in monetizing live streaming.
40:00 Legal issues with content rights, programming for dollars, and the pivot to gaming as Twitch.
45:00 Differentiating investor influence vs. founder-driven execution, social media’s emergence, and missed deals like Twitter.
50:00 Regrets around early venture decisions, rationality vs. intuition, and the limits of journalistic thinking in VC.
55:00 Reflections on truth, timing, and the impact of historical perspective in investment thinking.

Key Insights

1. The iPhone was not just a product—it was a platform shift. Initially perceived as a compact personal computer, the iPhone’s release in 2007 marked a pivotal transition in computing. Its eventual reliance on connectivity, cloud infrastructure, and a curated App Store created an entirely new ecosystem that transcended Apple’s roots in standalone devices. This revealed that the smartphone's power lay not just in hardware but in its entanglement with the growing capabilities of cloud computing.
2. Web 2.0 emerged from an in-between era where ‘nothing’ and ‘everything’ happened. Between the collapse of the dot-com bubble and the arrival of smartphones, the early 2000s seemed quiet on the surface but were actually fertile with infrastructure development. Fiber was laid, foundational software tools evolved, and key internet services like Google began forming. This paradox—an uneventful time that seeded today’s tech landscape—challenges how we measure technological progress.
3. Apple’s walled garden approach to apps reflected a deep-seated tension. While the introduction of the App Store was a game-changer, it clashed with Apple’s control-oriented DNA. Stewart Alsop II observed that despite apps fueling the iPhone’s success, Apple maintained a wary stance toward third-party developers. This tension continues to shape how innovation on the platform is regulated and monetized.
4. Cloud infrastructure reshaped the economic model of software. SaaS and cloud computing, catalyzed by AWS and others, introduced a shift from transactional to subscription-based revenue. The conversation draws a line from magazine subscriptions to software licensing and the rise of mobile app monetization, revealing how financial predictability became central to Internet business models.
5. Missed opportunities often stem from rational overthinking. The anecdote about passing on Elon Musk’s x.com underscores a broader pattern: being “right” doesn’t always lead to good investment outcomes. The rational investor might miss out on transformational bets simply because the risk doesn’t fit the prevailing model—a cautionary tale about the limits of logic in venture capital.
6. Twitch’s success grew from improvisation, not strategy. The journey from Justin.tv to Twitch is a testament to flexibility. Originally a quirky lifecasting experiment, the founders adapted to platform and market realities by focusing on video game streaming. The move wasn’t obvious or universally supported, but it reflected an intuitive grasp of emerging digital behavior—something investors initially overlooked.
7. The shift to real-time infrastructure reshaped identity and interaction. As the conversation touches on Anthropic, Claude, and the “Evernet,” a vision surfaces: one where real-time connectivity isn’t just technical but experiential. From managing servers to engaging with AI that directs our actions, humans are increasingly enmeshed in systems that blur autonomy, guidance, and even the boundary between tool and user.