Deel’s growth overshadows SpyGate, Claude learned new skills, and the great “momentum is moat” debate | E2194

Deel’s growth overshadows SpyGate, Claude learned new skills, and the great “momentum is moat” debate | E2194

Author: Jason Calacanis October 18, 2025 Duration: 1:18:28

Deel’s growth overshadows SpyGate, Claude learned new skills, and the great “momentum is moat” debate | EXXX


Today’s show:

*Deel’s growing fast enough that investors are overlooking the espionage allegations and jumping on board anyway. (LAUNCH now owns a lil taste of Deel, so Jason is on board!)

PLUS is the Mag 7 about to become the Mag 70… Why legendary investor Roelof Botha thinks VC is not an asset class… How startups can use capital as a weapon… AND Anthropic gave Claude more skills, which they hope will help pay their bills.

Timestamps:

(00:01:34) Jason’s excited for ski season and checking his favorite powder app, OpenSnow

(00:04:02) Why Jason’s done with meetings; he’s pulling a Doug Leone!

(00:06:27) Jason can tell the market’s heating up because people are starting to lose their minds.

(00:09:31) How much will global AI tools one day be worth? Alex is crunching the numbers.

(10:00) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!

(00:15:22) PREDICTION: The Mag7 is about to become the Mag70

(20:00) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twist

(00:25:36) Deel’s big raise… Why major growth overshadows spying allegations

(30:00) LinkedIn Ads: Start converting your B2B audience into high quality leads today. Launch your first campaign and get $250 FREE when you spend at least $250. Go to http://LinkedIn.com/ThisWeekinStartups to claim your credit.

(00:33:31) Why Roelof Botha says VC is a “return-free risk,” and not an “asset class.”

(00:40:49) The two reasons why VC firms end

(00:44:18) How startups can use capital as a weapon

(00:57:52) Anthropic gave Claude Skills to pay the bills

(01:00:51) Jason’s vision for what Grammarly could become


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X: https://x.com/lons


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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:

Miro - Help your teams get great done with Miro. Check out miro.com to find out how!


Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at LinkedIn Ads: Start converting your B2B audience into high quality leads today.


Launch your first campaign and get $250 FREE when you spend at least $250. Go to http://LinkedIn.com/ThisWeekinStartups to claim your credit.


Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland


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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.
Author: Language: en-us Episodes: 100

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