How to Raise a Seed Round in 2026: Ask Jason | E2294
This Week in Startups
Jason Calacanis
4.2 • 1.4K 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:
Follow Alex:
LinkedIn: https://www.linkedin.com/in/alexwilhelm
Follow 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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