
Why the most expensive Seed deals are the cheapest | E2299
From This Week in Startups by Jason Calacanis
June 10, 2026 · 1h 8m · Episode 2299
About this episode
The episode discusses the valuation of seed deals and the implications of recent IPO announcements in the tech industry.
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…
People in this episode
Host: Alex
Guests: Tomasz Tunguz, Michael Downing, Paige Doherty
Topics covered
- Seed investing
- startup economics
- AI spend
- venture capital
- IPO
- tokens-for-equity deals
Keywords
- Seed deals
- venture capital
- AI
- IPO
- startup economics
- tokens-for-equity
Sponsors
NetSuite, Deel, Squarespace
Mentioned in this episode
Organizations: Theory Ventures, Castalia Capital, Behind Genius Ventures, SpaceX, Sequoia
Products: Claude Fable 5
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