Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204
This Week in Startups
Jason Calacanis
4.4 • 1.3K Ratings
🗓️ 6 November 2025
⏱️ 84 minutes
🧾️ Download transcript
Summary
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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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.
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Transcript
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| 0:00.0 | Didi, you were promoted recently from principal to partner, I believe. I know you probably can't tell us all of Minlo's long-term plans for succession, but I am curious how often you think about your upper trajectory at the firm. And if there is more headroom for you to grow into, do you want to become one of its core leaders down the road? Is that a possibility? Tell me what it's like from your |
| 0:21.0 | hot seat. Honestly, I, I'm very thankful that they brought me in as somebody who had, |
| 0:27.5 | you know, no real experience in venture. Like I was really a person who just studied the craft |
| 0:32.5 | from a distance, right? I write online. I read everything I can. I was a part of a startup glean that went really well |
| 0:39.6 | from the very beginning to about the time I left and it's still doing fantastically. I just don't |
| 0:44.8 | have that approach to how I see Menlo. I mean, I joined this fantastic team very much to work as a team |
| 0:52.1 | together and reinvigorate what the firm stood for. |
| 0:56.0 | I mean, we've been around for 50 years. We're on our 17th fund. |
| 0:59.0 | So a part of the old guard really in terms of how storied the firm is. |
| 1:05.0 | But with any time, I think there is a time for resurgence and rebuilding of a firm. |
| 1:11.6 | And I don't know what the future lies, but I think every day about what we could be doing differently to be a different in venture. |
| 1:19.6 | And if you look at like the last four people that we've sort of hired at Menlo, you have Tim Tulli, who is a CTO of Splunk. You have Joff Redfern, who is the CPO |
| 1:29.2 | of Atlassian. You have Matt Craning, who did a PhD from Stanford and sold a unicorn cybersecurity |
| 1:34.8 | company. You have me. These are people who've operated businesses. And so one of the things that we |
| 1:40.9 | are trying really hard to do is sort of marry this set of people who |
| 1:46.0 | have been in the weeds and sort of seen like the brutality of what it takes to run a good |
| 1:50.7 | company with investors who get the finances who understand the long-term vision as well. |
| 1:57.3 | And we're very early on that arc. |
| 2:00.2 | Who knows what that future holds. |
| 2:02.2 | But right now, my main focus is, hey, let's focus on getting things right as a firm. |
| 2:08.5 | How do we invest? |
| 2:09.7 | What are our principles? |
... |
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