Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

Author: Jason Calacanis November 6, 2025 Duration: 1:23:50

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


Today’s show:

*On TWiST, Jason welcomes an all-star VC panel — Deedy Das of Menlo Partners and Jay Eum of GFT Ventures — for a deep dive into the shocking scale of early-stage AI raises, a transitional moment for investors, the growing importance of the “prosumer” market, ChatGPT’s insane smile curves, and much much more.

IN THIS EPISODE

  • What the panelists make of Roelof Botha’s exit from Sequoia… and is he really going anywhere…
  • Why Jason says VC is no longer the best way to get rich…
  • Why so many private companies are growing SO HUGE before going public…

And much more!

Timestamps:

(00:03:37) Jason is fresh from surviving Riyadh traffic but he’s here and introducing our all star panel

(00:04:03) Why Jason compares Riyadh to Silicon Valley in the 1960s

(00:05:21) Friend of the Pod Roelof Botha is stepping down at Sequoia… our insiders try to guess what might have happened…

(10:00) Crusoe - Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit crusoe.ai/startup to reserve your capacity for the latest GPUs today.

(00:13:11) Deedy moved up at Menlo without being a venture native… he shares the secrets behind his rise.

(00:19:09) Was Roelof wrong about “return-free risk”? Does more capital always = more great companies?

(20:00) 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!

(00:26:54) With so many private companies growing SO HUGE… when is the right time to go public? Considering the case of Glean and Stripe…

(30:00) AWS Marketplace - If you’re ready to really accelerate your sales cycle, AWS Marketplace is your next stop. Head to https://aws.com/startups to learn more.

(00:30:07) Why Jason says venture capital is no longer the best way to get rich

(00:32:34) Why AI apps are so appealing to enterprises after years of paying for SaaS

(00:36:32) The growing importance of “prosumers”

(00:37:31) Why Deedy says a smile curve is the most beautiful depiction of “Product Market Fit”

(00:44:36) Why it’s still tough to raise pre-seed money, even during an AI “boom”!

(00:46:08) Why Jason says the hardest job in the tech ecosystem is being an investor

(00:55:52) “Time is one of the primary drivers of venture capital return.” - Jay Eun

(00:57:42) Deedy on the shocking amounts being raised by early-stage AI companies

(01:00:21) Just how much DO VCs work compared to founders? The panel compares notes.

(01:02:53) Are some investors not doing diligence? Deedy on the speed of some AI deals.

(01:16:51) The panel picks their fav portfolio company of the moment (or one of their faves)


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

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:

Crusoe - Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit crusoe.ai/startup to reserve your capacity for the latest GPUs today.

Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit

AWS Marketplace - If you’re ready to really accelerate your sales cycle, AWS Marketplace is your next stop. Head to https://aws.com/startups to learn more.

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


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Substack: https://twistartups.substack.com


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


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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