logo
episode-header-image
Oct 28
1h 21m

Jason Unpacks Sequoia’s New Funds | E219...

Jason Calacanis
About this episode

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.


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:

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

Monarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/TWIST

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.


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


Follow TWiST:

Twitter: https://twitter.com/TWiStartups

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

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

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com


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

Up next
Today
What will be OpenAI’s IPO price? Place ya bets! | E2202
What will be OpenAI’s IPO price? Place ya bets! | EXXX*Polymarket’s sharps are already placing bets on when ChatGPT maker OpenAI will go public… and Jason and Alex want in on this action. They’re placing side wagers on how the House that Sam Altman built will be valued once it fi ... Show More
1h 18m
Oct 30
Grammarly is now Superhuman! CEO Shishir Mehrotra explains the rebrand | E2201
Today’s show:*Why rebrand an app with 40 million daily active users?On TWiST, Grammarly CEO Shishir Mehrotra swings by to explain why he’s renaming his company after the mail app he just purchased, Superhuman.Plus he’s giving us a first look at the startup’s new AI assistant, Sup ... Show More
1h 38m
Oct 29
iPhone Air is “inspiring,” and a first step toward Apple Glasses (w/ Zach Handshoe of SpatialGen) | E2200
Today’s show:Jason’s been skeptical on Apple lately, but he’s BLOWN AWAY by his new iPhone Air.Hear why JCal thinks Cupertino’s latest release is “completely inspiring,” and why he’s sure it’s the next step on the road to Apple Glasses.We’re chatting with LAUNCH founder Zach Hand ... Show More
1h 18m
Recommended Episodes
May 2025
Inside Devin: The world’s first autonomous AI engineer that's set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition)
Scott Wu is the co-founder and CEO of Cognition, the company behind Devin—the world’s first autonomous AI software engineer. Unlike other AI coding tools, Devin works like an autonomous engineer that you can interact with through Slack, Linear, and GitHub, just like with a remote ... Show More
1h 32m
Sep 23
How Microsoft is Fixing the Biggest AI Agent Problem
Want the guide to create AI Agents? get it here: https://clickhubspot.com/fhc Episode 77: Are we nearing a future where AI agents can autonomously tackle our biggest challenges—while remaining efficient, safe, and truly aligned with human goals? Matt Wolfe (https://x.com/mreflow) ... Show More
30m 8s
Sep 18
Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor)
Brendan Foody is the CEO and co-founder of Mercor, the fastest-growing company in history to go from $1M to $500M in revenue (in just 17 months!). At 22, he is also the youngest American unicorn founder ever. Mercor works with 6 of the Magnificent 7 and all top 5 AI labs to help ... Show More
1h 6m
Nov 2024
Clones, commerce & campaigns
Chris and Daniel dive into what Trump’s impending second term could mean for AI companies, model developers, and regulators, unpacking the potential shifts in policy and innovation. Next, they discuss the latest models, like Qwen, that blur the performance gap between open and cl ... Show More
53m 11s
May 2025
The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO)
Michael Truell is the co-founder and CEO of Anysphere, the company behind Cursor—the fastest-growing AI code editor in the world, reaching $300 million in annual recurring revenue just two years after its launch. In this conversation, Michael shares his vision for the future, les ... Show More
1h 11m
Dec 2024
AI is a money pit — here’s why investors don’t mind
AI investment is massive, but AI profits are not — and yet investors seem confident massive AI fundraising will one day translate into sizable AI profits. To break it down, Verge Deputy Editor Alex Heath guest hosts this episode of Decoder featuring Menlo Ventures partner Tim Tul ... Show More
33m 59s
Sep 21
From managing people to managing AI: The leadership skills everyone needs now | Julie Zhuo (Facebook VP, Sundial CEO, The Making of a Manager author)
Julie Zhuo is the former VP and Head of Design at Facebook (now Meta), author of the bestselling book The Making of a Manager, and co-founder of Sundial, an AI-powered data analysis company. Also, my first-ever podcast guest over 3 years ago!In our conversation, we discuss:1. The ... Show More
1h 36m
Aug 18
He built the top AI agent startup | Flo Crivello, Former PM, now CEO & Founder, Lindy AI
If you’ve ever said “I just wish I had an assistant who knew exactly how I think”... Lindy is that assistant. These agents aren’t demos. They’re real, customizable workflows anyone can build. No code.Flo Crivello (founder of Lindy and ex-Cruise/YC) joined us to show how his perso ... Show More
53m 10s
Aug 19
The AI Tool That Works Like 40 Employees (Saved 2000 Hours)
Want better results from your prompts? Get the Advanced Prompt Engineering guide: https://clickhubspot.com/wrm Episode 72: What if building an AI agent was as easy as texting a friend? Nathan Lands (https://x.com/NathanLands) sits down with repeat guest Flo Crivello (https://x.co ... Show More
34m 13s