Jason’s ultimate dream mega-purchase + Founder Q’s | E2228
This Week in Startups
Jason Calacanis
4.2 • 1.4K Ratings
🗓️ 29 December 2025
⏱️ 45 minutes
🧾️ Download transcript
Summary
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
Transcript
Click on a timestamp to play from that location
| 0:00.0 | Now that you're doing so well financially, what is a purchase that you'd like to make but can't |
| 0:04.0 | bring yourself to do so because it feels too extravagant? |
| 0:06.6 | Answer this honestly. |
| 0:07.7 | Tell the people what you, even Jason Collegendez, will not break out the checkbook for. |
| 0:12.2 | It's definitely private aviation. |
| 0:13.6 | I've been trying to hold off on doing this for a long time. |
| 0:17.5 | The great unjustifiable expense of spending, you know, $50,000 going somewhere or $100,000 |
| 0:23.6 | on a round trip, that seemed absurd to spend that. The other one, I would say that I sometimes |
| 0:29.4 | sweat is buying a really expensive sports car. I love Corvettes and I really want to buy a barn |
| 0:35.6 | dominium, which is like a big, open, fancy barn that's kind of like a |
| 0:39.4 | man cave, but Texas style. Do I buy this ZRX1 for $250,000, or do I buy $5,000 Corvettes and have a little |
| 0:50.7 | collection? A lot of these things become cognitive load. This week in startups |
| 0:55.1 | is brought to you by lemon.io. Building a great team is essential to any business. Lemon is a |
| 1:00.2 | marketplace of vetted, experienced engineers ready to take your company to the next level. Get 15% |
| 1:05.5 | off your first four weeks of developer time at lemon.io slash twist. Vanta. Compliance and security shouldn't be a dealbreaker |
| 1:12.7 | for startups to win new business. Vanta makes it easy for companies to get SOC2 reports fast. |
| 1:18.7 | Get $1,000 off for a limited time at vanta.com slash twist. Northwest Registered Agent. Starting |
| 1:25.3 | your business should be simple. With Northwest Registered |
| 1:28.4 | Agent, you can form your entire business identity in just 10 clicks and 10 minutes. From LLCs to |
| 1:34.2 | trademarks, domains to custom websites, they've got you covered. Get more privacy, more options, |
| 1:39.9 | and more done. Visit Northwestregisteredagent.com slash twist today. |
| 1:45.7 | Today's founder question, Jason, comes from our dear friends over at the R slash startups |
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