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This Week in Startups follows the arguments, decisions and personalities shaping technology businesses. Numbered discussions sit beside shorter clips about fundraising, hiring and investment, with AI…
This Week in Startups follows the arguments, decisions and personalities shaping technology businesses. Numbered discussions sit beside shorter clips about fundraising, hiring and investment, with AI forming a substantial part of the episode selection. The channel brings practical founder concerns into the same conversation as company strategy and industry news. Speculation is also visible in the topics, including proposed acquisitions and predictions about how AI could affect legal responsibility.
A conversation involving Justin Kan and Brian Chesky looks at rejection in the stories of Twitch and Airbnb. That founder-oriented perspective appears elsewhere in advice about raising money and the difficulties around team interviews. These subjects deal with moments when a young company depends on persuading other people: securing support, finding colleagues or continuing after an unwelcome response.
The AI discussions take the conversation towards open-source development, agents and the consequences of autonomous systems. An appearance by a Hugging Face co-founder connects those themes to the wider technology ecosystem. Other episodes debate what Apple might buy or which kinds of AI businesses venture investors would back, making room for contrasting views about company direction.
Founders and viewers who follow technology investment can use the channel to hear how those questions are framed and contested. Longer conversations provide room for a company story or an industry argument, while shorter segments isolate a particular piece of advice or prediction. The appeal is the overlap between running a startup and interpreting the environment around it: how a founder's immediate choices relate to the products, funding decisions and competitive bets being discussed elsewhere in the industry.
Latest episode
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…
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!
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