How to Raise a Seed Round in 2026: Ask Jason | E2294

How to Raise a Seed Round in 2026: Ask Jason | E2294

Author: Jason Calacanis May 29, 2026 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 breaks down the real math behind raising a seed round. Here’s the funnel: contact 150 firms, get 50 first meetings, convert 2o into second meetings, and close 2 term sheets.

PLUS Jason responds to viewer questions about why hardware is no longer a dirty word for investors, how to differentiate your startup from frontier-model companies like OpenAI, even when they’re in your niche. Plus a pitch for “Founder Community College,” and anecdotes from Lon’s European odyssey.


Thanks for the Questions:


Richard Corral: CEO of Quanto: https://quanto.co/

ØnProtons on X: https://x.com/0nProtons

SergeDawg on X: https://x.com/sergedawg

Mahika Golani

Peridot: https://www.tryperidot.com/

Shawn Sully on X: https://x.com/aroogle

Programs and Accelerators Mentioned:

Y Combinator: https://www.ycombinator.com/

Techstars: https://www.techstars.com/

Antler: https://www.antler.co/

PearX: https://pear.vc/pearx/

Sequoia ARC: https://www.sequoiacap.com/arc/

Kauffman Fellows: https://www.kauffmanfellows.org/

Companies and Startups Referenced:

Whoop: https://www.whoop.com/

Knightscope: https://knightscope.com/

Eight Sleep: https://www.eightsleep.com/

Cafe X: https://www.cafexapp.com/


Media Referenced:


New Yorker Sam Altman profile: https://www.newyorker.com/magazine/2026/04/13/sam-altman-may-control-our-future-can-he-be-trusted

Off-Duty Recommendations

Terra Kaffe Demi compact automatic espresso machine: https://www.terrakaffe.com/products/tk-demi

Osteria Pastella (Florence, Italy): https://www.osteriapastella.it/


Timestamps:


0:00 Inside the TWiST private group chat

3:25 How to react when an investor says your "too early."

6:50 The ultimate seed round funnel

8:48 Jason's new Associate in Training program

10:09 Grasshopper Bank - Time is money. Don't waste either. Go to https://grasshopper.bank/twist and get an exclusive $500 cash bonus just for opening an account.

18:28 How have the metrics for early-stage companies changed?

20:20 LinkedIn Jobs - Hire right, the first time. Post your first job and get $100 off towards your job post at https://LinkedIn.com/twist

22:34 TWiST Bounties update

23:43 Competing against frontier labs

30:03 What signals real investor-founder alignment?

30:14 Northwest Registered Agent - Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at https://northwestregisteredagent.com/twist

36:07 A crash course in Bay Area startup culture

40:15 Automatons-as-a-Service (AaaS)

42:29 Who in Silicon Valley does Jason really not like?

49:59 Museum Etiquette with Lon Harris


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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

Check out all our partner offers: https://partners.launch.co/

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

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Substack: https://twistartups.substack.com


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: 100

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