Why the most expensive Seed deals are the cheapest | E2299

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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