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

This Week In Startups is made possible by: PayPal: https://paypal.com/business The Conservation Fund: https://www.conservationfund.org/ Hostinger: https://hostinger.com/twist Plaud: https://plaud.ai/twist 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% off! 24:32 The Who Has the Most Subscribers Challenge 28:08 Is Apple waiting out the AI race on purpose 30:22 Hostinger: The all-in-one platform for domains, websites, email, and marketing. Go to https://hostinger.com/twist and use the code TWIST for an additional 10% off Black Friday and Cyber Monday 34:19 Is Canva an AI company? 39:08 True Believers who still want to make money 48:21 The $72.4B convertible-note charge, explained 51:03 How long does AI compute stay useful? 58:19 Jason’s monthly “Bitcoin is Dead” post 1:04:41 Alicorns are unicorns with pegasus wings 1:09:58 Subscribe to the TWiST Newsletter! Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Thank you to our partners: PayPal is built for all businesses. Get started at https://paypal.com/business The Conservation Fund: Thanks to our partner, The Conservation Fund! Learn more at https://www.conservationfund.org/ Hostinger: The all-in-one platform for domains, websites, email, and marketing. Go to https://hostinger.com/twist and use the code TWIST for an additional 10% off Black Friday and Cyber Monday 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% off! Check out all our partner offers: https://partners.launch.co/ Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Subscribe to our Substack Newsletters! 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