This Week in Startups · October 29, 2026 · 1h 12m

Is AI the new cigarettes? Our VC panel digs into Anthropic’s S-1

This Week in Startups convenes a VC roundtable to analyze Anthropic's S-1 filing, which shows an operating profit, a mostly non-cash $80.7 billion loss, and a 900% net revenue retention rate. Jason Calacanis hosts D.A. Wallach, Dave McClure, and Ben Black as they debate whether AI has become as addictive to enterprises as cigarettes, how the convertible-note charge distorts appearances, and whether Anthropic's mission-driven founders can compete with purely profit-focused rivals. The panel also touches on Apple's AI strategy, Canva's positioning, and the useful life of AI compute.

This summary was generated from show notes and public descriptions, not from a full transcript review. Details may contain inaccuracies.

Preview

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Anthropic's S-1 shows 900% net revenue retention0:00

Anthropic's S-1 filing reveals an operating profit and a net revenue retention rate of 900%, with customers spending dramatically more on intelligence than a year ago.

Claude ChatGPT Gemini

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The $80.7B loss is mostly a non-cash convertible-note charge48:21

Anthropic's $80.7 billion loss is largely non-cash, driven by a $72.4 billion convertible-note charge that does not represent cash leaving the business.

Claude ChatGPT Gemini

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