Is AI the new cigarettes? Our VC panel digs into Anthropic’s S-1 | E2356

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Today’s show:
Anthropic’s S-1 is here, and finally, we can start to develop a real understanding for the AI economy and whether the numbers add up. Anthropic shows an operating profit, a mostly non-cash $80.7 billion loss, and customers spending a shocking 9x what they were spending on intelligence just one year ago.
Is this the greatest business in history? Is AI now as addictive to enterprises as cigarettes once were to impressionable teens?
On this week’s VC Roundtable, Jason Calacanis is joined by D.A. Wallach (Time BioVentures), Dave McClure (Practical Venture Capital), and Ben Black (Akkadian Ventures / Powerlaw Corp.) to seek some answers.
They dig into the numbers, including that wild 900% net revenue retention, and consider how retail investors will consider the convertible-note charge behind their $80B loss. Plus they’ll debate whether Anthropic’s founders are really true believers driven by religious fervor, and if so, whether they’re destined to be out-competed by “rabid capitalists.”
Guests
D.A. Wallach on X: https://x.com/dawallach
Time BioVentures: https://www.timebioventures.com/
Dave McClure on X: https://x.com/davemcclure
Practical Venture Capital: https://practicalvc.com/
Trading Places podcast: https://www.youtube.com/@PracticalVentureCapital
Ben Black on LinkedIn: https://linkedin.com/in/benblack
Akkadian Ventures: https://akkadian.vc/
Powerlaw Corp: https://pwrl.com
Relevant Links
Anthropic’s S-1, by the numbers (Fortune): https://fortune.com/2026/10/27/anthropic-s1-ipo-filing-financials-profits/
900% NRR and an $80.7B loss that mostly ins’t (HackerNoon): https://hackernoon.com/anthropics-s-1-shows-163b-in-half-year-revenue-a-900percent-nrr-and-an-807b-loss-that-mostly-isnt
Tickertrends: https://tickertrends.io/
Replit makes OpenAI its default (TechCrunch): https://techcrunch.com/2026/10/17/replit-is-no-longer-working-with-anthropic-ceo-says/
Dario Amodei warns that rivals’ spending could risk bankruptcy (Fortune): https://fortune.com/2026/02/14/anthropic-ceo-dario-amodei-spending-capex-risk-ai-revenue-forecasts-bankruptcy
Machines of Loving Grace (Dario Amodei): https://www.darioamodei.com/essay/machines-of-loving-grace
Palantir CTO Shyam Sankar says AI researchers are taking up smoking (Fortune): https://fortune.com/2026/10/13/palantir-cto-shyam-sankar-ai-researchers-smoking-cigarettes-cure-cancer-artificial-general-intelligence-silicon-valley-mass-psychosis-effective-altruism/
Microsoft offers its first-ever voluntary buyouts (TechSpot): https://www.techspot.com/news/112174-microsoft-offers-voluntary-buyouts-thousands-us-workers-ai.html
Canva ranks among the top consumer AI apps (SmartCompany): https://www.smartcompany.com.au/artificial-intelligence/canva-new-ai-consumer-web-app-ranking-andreesen-horowitz/
SpaceX Q3: Musk says it could rent out its AI compute several times over (Constellation Research): https://www.constellationr.com/insights/news/spacexs-q3-musk-says-it-could-rent-out-its-ai-compute-several-times-over
Jason’s 2026 “Bitcoin is Dead” post: https://x.com/Jason/status/2114956980674605075
Jason to Michael Saylor: "there are better places to invest your money”: https://x.com/Jason/status/2115274438979756346
Timestamps:
0:00 Anthropic files its public S-1
4:58 Anthropic vs. OpenAI revenue run rates
9:20 PayPal is built for all businesses. Get started at https://paypal.com/business
10:02 “The greatest business in the history of capitalism”
11:58 Is intelligence the new tobacco?
18:08 The “meat sack constraint”
20:36 Thanks to our partner, The Conservation Fund! Learn more at https://www.conservationfund.org/
22:13 Plaud: If your work depends on conversations - interviews, meetings, calls - you need a Plaud NotePin S. You can check it out at https://plaud.ai/twist and use code TWIST for 10...