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 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

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: 50

This Week in Startups
Podcast Episodes
A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312 [not-audio_url] [/not-audio_url]

Duration: 1:14:03
This Week In Startups is made possible by: MongoDB - MongoDB.com/ai Rippling - Rippling.ai/twist Agree.com - agree.com Today's show: Hustle Fund's Eric Bahn and Chapter One's Jeff Morris Jr. join our venture capital roun…
Jason turned $11 and one tweet into 1.1M views | E2311 [not-audio_url] [/not-audio_url]

Duration: 1:29:50
This Week In Startups is made possible by: Quo https://quo.com/TWiST PayPal Open https://paypalopen.com Northwest Registered Agent https://northwestregisteredagent.com/twist Today's show: *Jason spent $11 building out Po…
Danny Bernstein left Big Tech to fund farm-bots | E2310 [not-audio_url] [/not-audio_url]

Duration: 1:00:53
This Week In Startups is made possible by: NetSuite https://NetSuite.ai/TWIST Squarespace https://squarespace.com/twist YSecurity https://YSecurity.io/TWIST Today's show: *America posted 400,000 farm jobs last year, and…
Why Data Is the Next $1 Trillion Market [not-audio_url] [/not-audio_url]

Duration: 1:06:00
This Week In Startups is made possible by: Digital Ocean - do.co/twist Agree.com - agree.com Every.io - every.io. Today's show: How many startups matter in tech? Fewer than you think. That's why venture capitalists are t…
$100T is managed by "human duct tape" | E2308 [not-audio_url] [/not-audio_url]

Duration: 58:01
This Week In Startups is made possible by: Northwest Registered Agent https://northwestregisteredagent.com/twist Vanta https://www.vanta.com/twist Sentry https://sentry.io/twist Today's show: *There are $100 trillion in…
Why the VC Hype Cycle Always Gets It Wrong | VC Roundtable | E2307 [not-audio_url] [/not-audio_url]

Duration: 1:14:10
This Week In Startups is made possible by: CLA - www.claconnect.com/withyou Northwest Registered Agent - www.northwestregisteredagent.com/twist Agree.com - www.agree.com Today's show: Forget the triple-triple-double-doub…
Chamath on why young people need more agency, risk, and adventure [not-audio_url] [/not-audio_url]

Duration: 1:12:05
This Week In Startups is made possible by: Plaud https://Plaud.ai/twist Shopify https://shopify.com/twist LinkedIn Jobs https://LinkedIn.com/twist Northwest Registered Agent https://northwestregisteredagent.com/twist Tod…
Why F1 Teams are Replacing Wind Tunnels with Smart Tape | E2305 [not-audio_url] [/not-audio_url]

Duration: 1:30:26
This Week In Startups is made possible by: Plaud - https://Plaud.ai/twistSentry - https://sentry.io/twistNorthwest Registered Agent-https://northwestregisteredagent.com/twistDigitalOcean - https://do.co/twist Today's sho…
Why the Future of Video Games is Moving Back to the Dinner Table [not-audio_url] [/not-audio_url]

Duration: 1:08:51
This Week In Startups is made possible by: Deel - deel.com/twist Northwest Registered Agent - northwestregisteredagent.com/twist LinkedIn - linkedIn.com/twist Today's show: Jason sits down with Brynn Putnam, CEO and foun…
The hottest running app has nothing to do with speed | E2303 [not-audio_url] [/not-audio_url]

Duration: 1:03:04
This Week In Startups is made possible by:Agree - https://agree.comQuo - https://quo.com/TWiSTSuperhuman - https://superhuman.comToday's show:In this double-header, Jason and Lon chat with Louis Phillips, founder of the…