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

Stewart Squared

In this episode of Stewart Squared, Stewart Alsop III sits down with Stewart Alsop II to explore the financial and technical foundations shaping today’s AI and cloud economy, from the staggering scale of CapEx and depreciation schedules to the sustainability of investments by Microsoft, Meta, OpenAI, and Anthropic. The conversation traces historical precedents like the fiber boom, Google’s rise, and the pivot from Justin.tv to Twitch, leading into a discussion of venture capital shifts, IPO trends, and the enduring importance of the “rule of 40.” They also examine Cloudflare’s emerging role in the open internet economy, the rise of agents and Amazon’s use of reinforcement learning gems, and pressing security challenges around AI scraping, ITAR data, and national infrastructure.

Check out this GPT we trained on the conversation

Timestamps

00:05 Stewart Alsop introduces the theme of CapEx and depreciation, setting the stage with numbers on massive 2025 infrastructure spending.
00:10 Stewart Alsop II explains depreciation schedules, cash vs GAAP accounting, and how fast AI infrastructure like Nvidia chips and server farms lose value.
00:15 The discussion shifts to Microsoft’s Azure strategy, OpenAI’s spending, and comparisons to the 1999 fiber boom where dark fiber overbuilds reshaped the internet.
00:20 Meta’s dual front in VR/AR and AI is questioned for sustainability, as acquisitions and billion-dollar hiring sprees raise risks.
00:25 Historical precedents emerge: Google’s speed in search, Facebook’s real-time newsfeed infrastructure, and the rise of Twitch from Justin TV through Emmett Shear’s pivot.
00:30 Venture capital lessons are highlighted, from early struggles to explosive growth, with reflections on Series A–C shifts, ZIRP, growth equity vs private equity, and the rule of 40.
00:35 Tesla vs Rivian valuations anchor a risk discussion, then focus moves to Cloudflare, intermediaries, AI web crawling, and pay-by-crawl monetization.
00:40 The episode closes with agents, RLGems, universal verifiers, Amazon and Apple’s data advantages, security concerns with ITAR breaches, and the future of an open internet.

Key Insights

1. Depreciation shapes the economics of AI infrastructure.
Stewart Alsop II explains how massive CapEx spending—such as $392 billion in 2025—must be matched against depreciation schedules, which spread the cost of assets like Nvidia chips and server farms over years. The challenge is that AI hardware becomes obsolete much faster than traditional assets, making the schedule a judgment call that influences sustainability.

2. Microsoft’s position differs from AI-first labs.
Unlike OpenAI or Anthropic, Microsoft already had Azure and enterprise infrastructure in place, so their incremental AI spending built on existing investments. This makes their approach more sustainable and less risky than startups burning cash to compete.

3. Meta faces a “two-front war.”
Meta’s massive CapEx is split between VR/AR hardware bets and AI infrastructure, stretching resources and raising questions about whether its cash flows from social media can continue to fund both without weakening the core business.

4. Historical precedents highlight today’s risks.
The fiber boom of the late 1990s, Google’s breakthrough with fast search, and the pivot from Justin.tv to Twitch show how infrastructure-heavy investments can collapse or succeed depending on timing, user demand, and business model clarity.

5. Venture capital dynamics have shifted.
Seed rounds remain risky and contrarian, but later rounds resemble private equity with safer bets and higher valuations. The “rule of 40” has become a standard measure for balancing growth and profitability when evaluating public companies.

6. Cloudflare positions itself as a gatekeeper.
With 80% of AI companies crawling the web through its network, Cloudflare’s pay-by-crawl model could redefine how publishers monetize access to their content, creating a new intermediary in the AI-driven internet economy.

7. Agents and security are the next frontier.
Amazon’s RLGems and universal verifiers illustrate the push to give AI agents personalization and autonomy, but this shift also heightens security risks. Breaches like ITAR data leaks underscore that the AI-driven world may be even more insecure than today’s internet.