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

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Oct 18, 2025

Deel's explosive growth is overshadowing espionage allegations, drawing investor interest. The discussion turns to the potential expansion of AI companies into trillion-dollar valuations. Momentum as a growth strategy faces scrutiny as Jason and Alex debate its effectiveness versus traditional methods. Plus, Anthropic enhances Claude's skills, opening doors for innovative AI applications in business operations. The impact of capital as a competitive tool in the startup landscape is a hot topic, revealing how deep funding can shape industry dynamics.

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ADVICE

Replace Meetings With Espresso Calls

Stop scheduling long meetings; use short backchannel calls with founders instead.
Ask for a founder's phone and call briefly to make faster decisions and reclaim time.

INSIGHT

AI Widens The Total Addressable Market

AI is expanding the addressable market by reinventing work and increasing per-person spend.
Jason projects many software categories will rapidly become trillion-dollar revenue markets.

ANECDOTE

Deel Raised Big Despite Spy Claims

Deel raised $300M despite spying allegations and reached a $1.2B ARR run-rate in September.
Jason revealed he owns a small position and recently messaged Deel's CEO to congratulate him.

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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

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

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

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

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YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

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Substack: https://twistartups.substack.com

Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916