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This Week in Startups

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

This Week in Startups

Jason Calacanis

Technology

4.21.4K Ratings

🗓️ 29 May 2026

⏱️ 58 minutes

🧾️ Download transcript

Summary

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


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

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

Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

Transcript

Click on a timestamp to play from that location

0:00.0

People in our secret group chat have questions for me.

0:03.8

Some might be spicy.

0:05.0

What do you think founders should be doing to try to give themselves a little bit of moat against open AI?

0:09.7

There's always going to be a feature set that the interface of the large language model is not going to add.

0:15.4

Out of all the people in Silicon Valley, who's the one person you really don't like the most and why?

0:22.0

Some people have damaged the reputation of the industry and the user base. And then some people have just maybe

0:27.7

screwed over friends of mine. I've been a consistent critic of every time he had a chance

0:33.6

to do the right thing for humanity, he picked his own self-interest. It's a level of

0:37.9

selfishness in decision-making and cutthroatness that I understand, but I wouldn't do. And I think

0:44.4

has damaged the reputation of the tech industry. The two people I'm talking about are two of the

0:49.0

most successful people ever in the history of business. This weekend startups is brought to you by

0:53.5

Northwest Registered Agent.

0:55.3

Get more when you start your business with Northwest. In 10 clicks in 10 minutes, you can form

1:00.6

your company and walk away with a real business identity. Learn more at Northwest Registeredagent.com

1:07.0

slash twist. LinkedIn. Thanks to our partners at LinkedIn. Post your job for free at LinkedIn.com

1:13.4

slash twist, then promote it to get access to LinkedIn jobs new AI assistant. And Grasshopper Bank.

1:20.2

Time is money. Don't waste either. Go to grasshopper. Bank slash twist and get an exclusive

1:25.6

$500 cash bonus just for opening an account.

1:29.3

All right.

1:30.4

Lon Harris is here.

1:31.4

I'm Jason Kalakannis.

1:32.7

People in our secret group chat on X, formerly known as Twitter, have questions for me.

...

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