Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

Author: Jason Calacanis December 29, 2025 Duration: 45:03

This Week In Startups is made possible by:


Northwest Registered Agent- https://www.northwestregisteredagent.com/twist


Vanta - http://www.vanta.com/twist


Lemon IO - https://lemon.io/twist


Today’s show: 


Jason’s already a millionaire many times over… but what are the huge, blockbuster, dream purchases that he’s still holding off on? BESIDES the private jet we all know he wants? The Noti Gang has asked, and JCal finally answers, on a holiday TWiST where we’re taking questions from viewers and fans.


Check out the episode for lots more intriguing queries, like how to push forward and glean useful information when your first customers aren’t using your product the way you’d envisioned. Plus, is there room for both AI agents and great SaaS startups in the coming years? Hear why Jason thinks there IS.


AND we’ve got the very last Gamma Pitch Deck Competition entry before we announce our winner in the new year. Check out AskHumans, an innovative approach to improving market research.


Timestamps: 


(00:00) On a special holiday TWiST, we’re answering YOUR pressing Founder Questions!


(8:35) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!


(09:35) What should a founder do when a VC reaches out cold?


(13:37) The importance of maintaining “ball control”


(15:35) A European founder asks: Should I take European investments if they’re targeting American customers?


(19:47) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist


(20:51) A member of the Noti gang asks for JCal’s dream mega-purchases


(24:12) Why Jason thinks there’s room for BOTH AI agents and great SaaS companies


(27:18) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist


(28:23) It’s our final Gamma pitch with Zak from AskHumans!


(29:24) How AskHumans uses AI to improve on marketing surveys and research


(34:33) Management and measurement were designed before computers could understand language… why this matters.


(35:48) Why no one ever wants to give feedback in a video


(39:01) Why Zak’s pitch is “two chapters of the same story”… and was this a pivot?


(44:14) Why founders need to assume LLMs are going to get exponentially better


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Check out the TWIST500: https://twist500.com


Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp


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Follow Lon:


X: https://x.com/lons


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Follow Alex:


X: https://x.com/alex


LinkedIn: https://www.linkedin.com/in/alexwilhelm/


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Follow Jason:


X: https://twitter.com/Jason


LinkedIn: https://www.linkedin.com/in/jasoncalacanis/


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Thank you to our partners:


(8:35) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!


(19:47) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist


(27:18) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist


Great TWIST interviews: 


Will Guidara

https://youtu.be/pvJa2pzuXWQ


Eoghan McCabe

https://youtu.be/9dHN4YFkgv4


Steve Huffman

https://podcasts.apple.com/us/podcast/reddit-ceo-steve-huffman-on-mod-revolt-building-a/id315114957?i=1000617333424


Brian Chesky

https://podcasts.apple.com/ca/podcast/airbnb-ceo-brian-chesky-on-early-rejection-customer/id315114957?i=1000611761112


Bob Moesta

https://youtu.be/y2UMzSqX94Q


Aaron Levie

https://podcasts.apple.com/ca/podcast/box-ceo-aaron-levie-breaks-down-box-ai-and-generative/id315114957?i=1000612384545


Sophia Amoruso

https://podcasts.apple.com/ca/podcast/sophia-amoruso-on-branding-raising-a-fund-portfolio/id315114957?i=1000601352978


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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