Why the most expensive Seed deals are the cheapest | E2299 episode artwork

EPISODE · Jun 10, 2026 · 1H 8M

Why the most expensive Seed deals are the cheapest | E2299

from This Week in Startups · host Jason Calacanis

This Week In Startups is made possible by:NetSuite - Netsuite.com/TWiSTDeel - Deel.com/TWiSTSquarespace - Squarespace.com/TWiSTTwo days before SpaceX launches the largest IPO in history at a flat $135/share, our VC roundtable drops a scorcher: The top 1% of seed deals might actually be underpriced. Plus: the "Sequoia scam" dual-tranche controversy, tokens-for-equity deals, and whether Claude Fable 5 is a true step function.Tomasz Tunguz (Theory Ventures), Michael Downing (Castalia Capital), and Paige Doherty (Behind Genius Ventures) join Alex to go deep on Seed investing, startup economics, AI spend, and the impact of smarter AI on the founder journey.Guest Links:Tomasz Tunguz: https://x.com/ttunguzTheory Ventures: https://theoryvc.com/Michael Downing: https://www.linkedin.com/in/michaeldowning/Castalia Capital: https://castalia.capital/Paige Doherty: https://x.com/paigefinnnBehind Genius Ventures: https://www.behindgeniusventures.comShow Links:Anthropic’s IPO announcement: https://www.anthropic.com/news/confidential-draft-s1-secOpenAI’s IPO announcement: https://openai.com/index/openai-submits-confidential-s-1/Bending Spoons F-1 filing: https://www.sec.gov/Archives/edgar/data/2004711/000110465926071170/tm2613674-7_f1.htmSpaceX IPO filing: https://www.sec.gov/Archives/edgar/data/1181412/000162828026040364/spaceexplorationtechnologib.htmBrendan Foody’s post on Sequoia: https://x.com/BrendanFoody/status/2063470286515683759Claude Fable 5: https://www.anthropic.com/news/claude-fable-5-mythos-5OpenRouter data on Chinese models: https://openrouter.ai/rankings?view=daySaronic: https://www.saronic.com/MotherDuck: https://motherduck.com/Nox Metals: https://noxmetals.co/Timestamps:0:00 Tomasz Tunguz, Michael Downing & Paige Doherty join2:07 The SpaceX IPO and the IPO window4:22 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!6:30 The new bar: 10x growth (not 3x) to raise a great Series A8:46 Net-new AI budgets9:46 Squarespace: Turn your idea into a beautiful website! Go to https://www.squarespace.com/twist for a free trial. When you're ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain.11:09 How some founders are outgrowing venture capital11:44 The power pendulum swings back to founders12:46 SpaceX vs. OpenAI vs. Anthropic: Which IPO is most enticing?19:53 Deel - Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, get visas handled fast, and get back to building. Visit https://deel.com/twist to learn more.26:07 Tokens-for-equity, GPU-hours-for-equity & the financialization of compute28:35 Founders airing VC dirty laundry (napping VCs included)29:56 Netsuite - The business landscape is very chaotic right now. That's why you need NetSuite, by Oracle. Get the free business guide Demystifying AI at https://Netsuite.com/TWiST36:38 Claude Fable 5 first impressions: pricing, benchmarks & orchestration45:42 Where value accrues: application layer vs. models vs. private data1:00:06 Nationalization of AI labs: Bernie Sanders, Sam Altman & Trump agree?!1:01:25 Portfolio spotlights: Saronic, MotherDuck, and Nox MetalsSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpFollow Lon:X: https://x.com/lonsFollow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisGreat TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarlandCheck out Jason’s suite of newsletters: https://substack.com/@calacanis

This Week In Startups is made possible by:NetSuite - Netsuite.com/TWiSTDeel - Deel.com/TWiSTSquarespace - Squarespace.com/TWiSTTwo days before SpaceX launches the largest IPO in history at a flat $135/share, our VC roundtable drops a scorcher: The top 1% of seed deals might actually be underpriced. Plus: the "Sequoia scam" dual-tranche controversy, tokens-for-equity deals, and whether Claude Fable 5 is a true step function.Tomasz Tunguz (Theory Ventures), Michael Downing (Castalia Capital), and Paige Doherty (Behind Genius Ventures) join Alex to go deep on Seed investing, startup economics, AI spend, and the impact of smarter AI on the founder journey.Guest Links:Tomasz Tunguz: https://x.com/ttunguzTheory Ventures: https://theoryvc.com/Michael Downing: https://www.linkedin.com/in/michaeldowning/Castalia Capital: https://castalia.capital/Paige Doherty: https://x.com/paigefinnnBehind Genius Ventures: https://www.behindgeniusventures.comShow Links:Anthropic’s IPO announcement: https://www.anthropic.com/news/confidential-draft-s1-secOpenAI’s IPO announcement: https://openai.com/index/openai-submits-confidential-s-1/Bending Spoons F-1 filing: https://www.sec.gov/Archives/edgar/data/2004711/000110465926071170/tm2613674-7_f1.htmSpaceX IPO filing: https://www.sec.gov/Archives/edgar/data/1181412/000162828026040364/spaceexplorationtechnologib.htmBrendan Foody’s post on Sequoia: https://x.com/BrendanFoody/status/2063470286515683759Claude Fable 5: https://www.anthropic.com/news/claude-fable-5-mythos-5OpenRouter data on Chinese models: https://openrouter.ai/rankings?view=daySaronic: https://www.saronic.com/MotherDuck: https://motherduck.com/Nox Metals: https://noxmetals.co/Timestamps:0:00 Tomasz Tunguz, Michael Downing & Paige Doherty join2:07 The SpaceX IPO and the IPO window4:22 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!6:30 The new bar: 10x growth (not 3x) to raise a great Series A8:46 Net-new AI budgets9:46 Squarespace: Turn your idea into a beautiful website! Go to https://www.squarespace.com/twist for a free trial. When you're ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain.11:09 How some founders are outgrowing venture capital11:44 The power pendulum swings back to founders12:46 SpaceX vs. OpenAI vs. Anthropic: Which IPO is most enticing?19:53 Deel - Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, get visas handled fast, and get back to building. Visit https://deel.com/twist to learn more.26:07 Tokens-for-equity, GPU-hours-for-equity & the financialization of compute28:35 Founders airing VC dirty laundry (napping VCs included)29:56 Netsuite - The business landscape is very chaotic right now. That's why you need NetSuite, by Oracle. Get the free business guide Demystifying AI at https://Netsuite.com/TWiST36:38 Claude Fable 5 first impressions: pricing, benchmarks & orchestration45:42 Where value accrues: application layer vs. models vs. private data1:00:06 Nationalization of AI labs: Bernie Sanders, Sam Altman & Trump agree?!1:01:25 Portfolio spotlights: Saronic, MotherDuck, and Nox MetalsSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpFollow Lon:X: https://x.com/lonsFollow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisGreat TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarlandCheck out Jason’s suite of newsletters: https://substack.com/@calacanis

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Why the most expensive Seed deals are the cheapest | E2299

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This Week In Startups is made possible by:NetSuite - Netsuite.com/TWiSTDeel - Deel.com/TWiSTSquarespace - Squarespace.com/TWiSTTwo days before SpaceX launches the largest IPO in history at a flat $135/share, our VC roundtable drops a scorcher: The...

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