In this episode of Stewart Squared, hosts Stewart Alsop II and his son Stewart Alsop III, sits down with journalist and author Fred Vogelstein, known for his book Crazy Stupid Tech, to explore how technology, finance, and media are colliding in the age of AI. The conversation moves from Cloudflare’s emerging influence on AI web infrastructure and Google’s shifting search economy to the echoes of the 1999 tech bubble and the leverage risks in today’s crypto and private credit markets. Fred connects these financial dynamics to broader issues like middle-class decline, automation, and America’s uneasy economic balance with China. For more on Fred’s work, check out his book Crazy Stupid Tech and his reporting on Cloudflare and AI, and more subscribing to his innovation newsletter with Om Malik at CrazyStupidTech.com.

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Timestamps

00:00 Stewart Alsop and Stewart Alsop II welcome Fred Vogelstein to discuss Crazy Stupid Tech, Cloudflare, AI crawling, and Google’s dominance in search.
05:00 Vogelstein explains how Cloudflare’s control of 20% of web traffic gives publishers leverage against AI firms and Google’s search-to-AI transition.
10:00 The group compares today’s AI surge to the 1999 dot-com bubble, with parallels in hype, investment, and balance-sheet-driven spending.
15:00 They revisit the dual Internet and broadband bubbles and recall the 2000–2001 collapse that reshaped Silicon Valley.
20:00 Vogelstein questions assumptions about endless data-center growth and Transformer model efficiency, hinting at over-investment.
25:00 Discussion shifts to private credit, crypto leverage, and echoes of 1929’s systemic risk.
30:00 The hosts explore “too big to fail” thinking, national security, and global power shifts between the U.S. and China.
35:00 Debate over the dollar’s reserve status and potential yuan challenge connects to deflation and economic uncertainty.
40:00 Vogelstein argues AI could rebuild the American middle class by turning coding into a new industrial skill.
45:00 They reflect on generational divides, immigration, and historical memory shaping political polarization.
50:00 Conversation turns to Argentina’s scarcity economy and how chaos breeds innovation and resilience.
55:00 The trio concludes with optimism about AI as a personal tutor, onshoring, additive manufacturing, and the promise of renewed American industry.

Key Insights

1. Cloudflare’s strategic role in the AI ecosystem: Fred Vogelstein highlights how Cloudflare, led by Matthew Prince, occupies a pivotal position in managing AI web traffic, controlling around 20% of internet flows. This gives it unique leverage to force AI companies and publishers into negotiations over content usage and compensation—something Google has long resisted. Vogelstein sees this as a potential rebalancing of power between tech platforms and media creators.
2. Google’s existential search dilemma: The conversation underscores Google’s dependence on search revenue, which still represents over 60% of its business. As users shift toward AI-driven interfaces like Gemini, even a partial decline in search use could threaten Google’s financial foundation—an “extinction-level event,” as Vogelstein puts it.
3. Echoes of past bubbles: Drawing on his decades covering tech and finance, Vogelstein compares today’s AI boom to the 1999 Internet bubble, with enormous valuations and speculative enthusiasm. However, this time the money is coming from corporations with massive balance sheets rather than pure startups, creating a slower but potentially deeper form of risk.
4. Hidden leverage in the financial system: The group explores how private credit and crypto markets—largely unregulated and opaque—mirror the risky leverage dynamics of 1929. Vogelstein warns that while tech companies appear stable, the real vulnerability may lie in the unseen parts of the financial system funding them.
5. The geopolitics of AI and national security: The discussion broadens to how AI infrastructure investment has become a geopolitical contest between the U.S. and China. Data centers, chips, and compute capacity are now viewed as strategic assets, turning the tech race into a matter of state power and economic survival.
6. AI’s potential to restore middle-class opportunity: Despite his caution about financial bubbles, Vogelstein remains hopeful that generative AI could democratize innovation—allowing ordinary workers to “code” and automate without elite training, perhaps rebuilding the middle class hollowed out by globalization.
7. Cycles of disruption, renewal, and resilience: The episode closes on a philosophical note: every technological revolution disrupts before it rebuilds. From the offshoring of U.S. manufacturing to the rise of automation and scarcity economies like Argentina’s, the trio argues that chaos can spark renewal, and AI’s true promise may lie in that creative tension between collapse and reinvention.