Why the most expensive Seed deals are the cheapest | E2299 from This Week in Startups

This Week in Startups

Jason Calacanis

Episodes

About

Reviews

Promote

Why the most expensive Seed deals are the cheapest | E2299

1 hour 8 minutes Posted Jun 10, 2026 at 11:41 pm.

Tomasz Tunguz, Michael Downing & Paige Doherty join

The SpaceX IPO and the IPO window

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!

The new bar: 10x growth (not 3x) to raise a great Series A

Net-new AI budgets

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.

How some founders are outgrowing venture capital

The power pendulum swings back to founders

SpaceX vs. OpenAI vs. Anthropic: Which IPO is most enticing?

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.

Tokens-for-equity, GPU-hours-for-equity & the financialization of compute

Founders airing VC dirty laundry (napping VCs included)

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

Claude Fable 5 first impressions: pricing, benchmarks & orchestration

Where value accrues: application layer vs. models vs. private data

Nationalization of AI labs: Bernie Sanders, Sam Altman & Trump agree?!

Portfolio spotlights: Saronic, MotherDuck, and Nox Metals

0:00

1:08:23

Download MP3

Share at current time

Show notes

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:

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

← See all 1496 episodes of This Week in Startups