Jason Unpacks Sequoia’s New Funds | E2199
This Week in Startups
Jason Calacanis
4.4 • 1.3K Ratings
🗓️ 28 October 2025
⏱️ 82 minutes
🧾️ Download transcript
Summary
Today’s show:
Australia has accused Microsoft of employing a dark pattern… Hear why Jason says these kinds of sneaky tactics aren’t usually worth it.
It’s a brand-new Monday TWiST and it’s PACKED with news. In addition to Australia’s allegations against MSFT, we’re looking at Chinese drone fails and wondering how live experiences will change in the age of AI.
PLUS has Tesla finally “solved” FSD after years of promises? Does it matter that so much of Mercor’s revenue goes back out to contractors? Do Chinese LLMs have a major advantage when it comes to the stock market over Western counterparts? Why Jason avoids overseas deals when he doesn’t speak the language or know the culture. And much more!
Timestamps:
(00:03:44) Fall is here! And Jason is already looking ahead to “BFCM” and the holiday season.
(00:07:13) We’re bringing back the TWiSTies and a Prediction 2026 show
(00:07:33) People are using AI to create fake receipts for fraudulent invoices!
(10:00) Pipedrive - Bring clarity and control to your sales process with Pipedrive, the #1 CRM for small and medium sized businesses. Supercharge your sales today. Start with a 30-day free trial at pipedrive.com/twist.
(00:14:23) It’s earnings week for Meta AND Alphabet AND Microsoft AND AMAZON!
(00:19:55) What happened with the disastrous Chinese drone and fireworks show?
(20:00) Monarch - Thanks to our partner, Monarch! Try the app and get 50% off your first year by visiting monarchmoney.com/twist.
(00:27:37) Why Jason thinks live experiences are going to get much bigger and more impressive in the age of AI
(00:29:34) Why Tesla is training FSD on synthetic data now… Has FSD finally been “solved”?
(30:00) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit https://www.aws.amazon.com/startups/credits
(00:45:10) What’s going on with these new Sequoia funds? Jason unpacks the strategy…
(00:50:50) Jason doesn’t like to invest overseas unless he speaks the language and knows the culture
(00:51:11) Jason’s thoughts on the controversy surrounding Sequoia partner Shaun Maguire’s comments
(00:58:34) Mercor pays out 60-70% of its toppling revenue to contractors… does this MATTER?
(01:06:14) Do Chinese LLMs have a major advantage when it comes to investing? (Humans are now betting on all this on PolyMarket)
(01:09:45) Australia alleges that Microsoft is employing a dark pattern… why Jason says that’s a problem.
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Transcript
Click on a timestamp to play from that location
| 0:00.0 | Normally, here on Twist, we don't talk about earnings because it's not a startup story. |
| 0:03.9 | And so we just leave it to CNBC. |
| 0:05.7 | We leave it to Bloomberg and we let them do it. |
| 0:07.8 | This week, however, I just want to tell everyone out there who is building a startup that they may want to pay a little bit of attention to a couple of reports. |
| 0:14.5 | And the reason why is this week we're going to hear from meta and alphabet and Microsoft and Amazon, which is essentially the hyper-scaler set. |
| 0:23.0 | And all these companies have been pouring tens of billions of dollars into AI infrastructure. |
| 0:27.2 | And as of the end of the last quarter, they were saying, we are so compute-constrained. |
| 0:30.9 | It is so tough out here for us to get enough GPUs. |
| 0:33.6 | And so everyone is buying into the AI boom because there's still needed capacity. |
| 0:38.2 | And that implies demand. |
| 0:39.5 | It's going to be good for Nvidia, good for open AI, good for everybody. |
| 0:42.9 | But what we don't know is what they're going to say this time about not only the trailing three months, but also the rest of this year and into early 2006. |
| 0:50.1 | All of Wall Street wants to know that they are laser focused on this particular topic. |
| 0:53.9 | And that means we're going to get a good look at what they are seeing. |
| 0:57.9 | So if you pay attention to no public markets whatsoever, and as a founder, I get it. |
| 1:01.8 | Totally fine. |
| 1:02.7 | But you may want to tune into a couple of these because there's going to be interesting notes about industries that are buying. |
| 1:07.1 | Yeah, we should cover this for sure because it does relate to the overall opportunity for |
| 1:13.2 | AI and what's interesting about this cohort of companies is of the four you mentioned meta alphabet |
| 1:18.7 | Microsoft Amazon mama of the mama three are the top three cloud computing providers in the world, Alphabet, Microsoft, Amazon. |
| 1:30.2 | So they are going to have two-sided discussions about AI. First, Amazon's going to be talking |
| 1:37.4 | about robotics and all that leaked information, and they're going to be asked by analysts. |
... |
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