Why the most expensive Seed deals are the cheapest | E2299

Why the most expensive Seed deals are the cheapest | E2299

Author: Jason Calacanis June 11, 2026 Duration: 1:08:23
This Week In Startups is made possible by: NetSuite - Netsuite.com/TWiST Deel - Deel.com/TWiST Squarespace - Squarespace.com/TWiST Two 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/ttunguz Theory Ventures: https://theoryvc.com/ Michael Downing: https://www.linkedin.com/in/michaeldowning/ Castalia Capital: https://castalia.capital/ Paige Doherty: https://x.com/paigefinnn Behind Genius Ventures: https://www.behindgeniusventures.com Show Links: Anthropic's IPO announcement: https://www.anthropic.com/news/confidential-draft-s1-sec OpenAI'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.htm SpaceX IPO filing: https://www.sec.gov/Archives/edgar/data/1181412/000162828026040364/spaceexplorationtechnologib.htm Brendan Foody's post on Sequoia: https://x.com/BrendanFoody/status/2063470286515683759 Claude Fable 5: https://www.anthropic.com/news/claude-fable-5-mythos-5 OpenRouter data on Chinese models: https://openrouter.ai/rankings?view=day Saronic: https://www.saronic.com/ MotherDuck: https://motherduck.com/ Nox Metals: https://noxmetals.co/ Timestamps: 0:00 Tomasz Tunguz, Michael Downing & Paige Doherty join 2:07 The SpaceX IPO and the IPO window 4:22 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 A 8:46 Net-new AI budgets 9:46 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 capital 11:44 The power pendulum swings back to founders 12:46 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 compute 28:35 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/TWiST 36:38 Claude Fable 5 first impressions: pricing, benchmarks & orchestration 45:42 Where value accrues: application layer vs. models vs. private data 1:00:06 Nationalization of AI labs: Bernie Sanders, Sam Altman & Trump agree?! 1:01:25 Portfolio spotlights: Saronic, MotherDuck, and Nox Metals 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 Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason's suite of newsletters: https://substack.com/@calacanis

Every week, Jason Calacanis dives headfirst into the swirling vortex of Silicon Valley and global tech with This Week in Startups. It’s a direct line to the conversations shaping our digital future, moving far beyond surface-level news. You’ll hear Jason’s unfiltered analysis on everything from market shifts and media trends to the underlying mechanics of building a business, all delivered with a blend of enthusiasm and seasoned skepticism. The core of this podcast, however, lies in the guests. Jason sits down with the very people driving change-founders who have scaled impossible heights, operators managing daily chaos, and investors who spot trends before they become obvious. These conversations are less like formal interviews and more like insider debriefs, pulling back the curtain on real strategies, painful failures, and unexpected successes. For anyone curious about how technology is built, funded, and ultimately changes the world, this series offers a front-row seat. It’s the context behind the headlines, providing a deeper understanding of the forces at play in startups and technology. Tune in for a consistently engaging and insightful look at the ecosystem, straight from someone who lives and breathes it.
Author: Language: en-us Episodes: 50

This Week in Startups
Podcast Episodes
Why SpaceX Buying Cursor Changes Everything [not-audio_url] [/not-audio_url]

Duration: 1:41:05
This Week In Startups is made possible by: Deel - deel.com/twist LinkedIn - linkedIn.com/twist Northwest Registered Agent - northwestregisteredagent.com/twistPlaud - https://Plaud.ai/twist Today's show: Anthropic stabbed…
The Startup Building the First Hotel on the Moon… [not-audio_url] [/not-audio_url]

Duration: 1:40:54
This Week In Startups is made possible by: Every.io - visit every.io Sentry.io - sentry.io/twist Vanta - vanta.com/twist Today's show: The next SpaceX won't be building rockets; it'll build the first hotel on the Moon. T…
SpaceX IPO Day: What Wall St. and the media missed | E2300 [not-audio_url] [/not-audio_url]

Duration: 1:19:56
This Week In Startups is made possible by: Plaud https://Plaud.ai/twist Pilot https://pilot.com/twist Agree https://agree.com IM8 Health https://IM8health.com/twist After watching Elon build out his rocket (and AI) compa…
The AI Tutor That Makes Kids Actually Think | E2298 [not-audio_url] [/not-audio_url]

Duration: 1:00:19
The AI Tutor That Makes Kids Actually Think | E2298 This Week In Startups is made possible by: Northwest Registered Agent https://northwestregisteredagent.com/twist LinkedIn Jobs https://LinkedIn.com/twist Shopify https:…
The project SpaceX's first employee raised $500M for [not-audio_url] [/not-audio_url]

Duration: 1:01:36
This Week In Startups is made possible by: Northwest Registered Agent - NorthwestRegistereAagent.com/TWIST Every - Every.io Sentry - Sentry.io/TWIST Today's show: Want to get to space? Several launch companies can help y…
This Startup Fused Human Brain Cells with Silicon Chips | E2295 [not-audio_url] [/not-audio_url]

Duration: 1:06:16
This Week In Startups is made possible by: Deel https://deel.com/twist Quo https://quo.com/TWiST LinkedIn Jobs https://LinkedIn.com/twist Today's show: Cortical Labs is the world's first company selling biological comput…
How to Raise a Seed Round in 2026: Ask Jason | E2294 [not-audio_url] [/not-audio_url]

Duration: 57:55
This Week In Startups is made possible by: Grasshopper Bank https://grasshopper.bank/twistLinkedIn Jobs https://LinkedIn.com/twistNorthwest Registered Agent https://northwestregisteredagent.com/twist Today's show: Jason…
The Drone Company Quietly Taking Over Delivery [not-audio_url] [/not-audio_url]

Duration: 1:01:23
This Week In Startups is made possible by: Render - render.com/twist Deel - deel.com/twist Northwest Registered Agent - northwestregisteredagent.com/twist Today's show: The "Ryanair of drone delivery" just raised $50 mil…