Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

Author: Jason Calacanis November 18, 2025 Duration: 1:14:15

*Are we finally reaching Peak eVTOL? Jason and Alex on Joby’s big Abu Dhabi moves and Archer’s purchase of LA’s Hawthorne Airport.

On a PACKED Monday TWiST, Jason is BACK from MENA and Tokyo. Hear tales from his whirlwind trips launching new Founder University satellite programs… and find out why construction and fintech are BOOMING across the Middle East.

PLUS Ramp raised $300M… here’s why Alex calls the round “pretty baller.” We question why AI companies are growing SO MUCH FOUNDER than their SaaS counterparts. We’re digging into the Problem with Dropbox.

AND we’re saying goodbye to KitKat, the beloved SF bodega cat who was reportedly run over by a Waymo. Here’s why Jason’s not too broken up about it (but he’s JUST JOKING!)

👉  Register here for Founder University Japan’s kickoff: https://luma.com/cm0x90mk


Today’s show:


Timestamps:

(2:17) Big takeaways from Jason’s MENA Founder University trip

(6:54) Why construction and fintech are booming across the Middle East(9:56) Netsuite. The business landscape is very chaotic right now. That’s why you need NetSuite, by Oracle. Download the CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist

(12:35) Everything was very different at Founder University Japan! It’s coming in January.

(15:59) Ramp raised $300M at a $32B valuation… why Alex says it’s “pretty baller”

(17:15) Ramp says AI agents are making money more intelligent… the heck does that mean?

(19:26) We’re building more space for machines than humans now… and why Jason’s not sure this will last

(19:48) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(23:41) Why AI is growing SO MUCH faster than even top SaaS companies

(25:32) The Problem with Dropbox…

(30:21) DevStats - DevStats integrates your dev work and your business goals into a shared language that everyone can understand. Get 20% off, plus access to their dedicated Slack channel. Just go to https://www.DevStats.com/twist.

(32:39) Jason ate his way across Tokyo… here’s all the deets

(33:16) RIP KitKat, beloved SF bodega cat killed by a Waymo

(39:03) So who SHOULD get to make decisions about local roads?

(44:15) Dario Amodei from Anthropic shares Jason’s concerns about AI job displacement

(52:02) What’s going on with crypto prices? Is this vibe-based? Just based on the wider economy?

(58:14) Viewer questions: What strategies should founders employ in the current fundraising landscape?

(1:02:42) Bezos RETURNS to the C-Suite. What IS “Project Prometheus”?

(1:10:24) Jason thinks Bezos still returns to Amazon at some point… or runs for President.


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


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


Thank you to our partners:

(9:56) Netsuite. The business landscape is very chaotic right now. That’s why you need NetSuite, by Oracle. Download the CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist

(19:48) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist

(30:21) DevStats - DevStats integrates your dev work and your business goals into a shared language that everyone can understand. Get 20% off, plus access to their dedicated Slack channel. Just go to https://www.DevStats.com/twist.


Check out Jason’s suite of newsletters: https://substack.com/@calacanis


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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.
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