The Grammarly–Superhuman Megadeal, plus TWiST 500 chats with LabelBox and Apptronik’s founders | E2146

This Week in Startups

Jason Calacanis

Technology

4.4 • 1.3K Ratings

🗓️ 1 July 2025

⏱️ 87 minutes

🔗️ Recording | iTunes | RSS

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Summary

Today’s show:

Grammarly is acquiring the beloved email app Superhuman! In today’s extremely timely episode, @alex sits down with Grammarly CEO Shishir Mehrotra and Superhuman founder Rahul Vohra to unpack why they’re merging, how they plan to combine apps and AI agents, and what it means for the future of email and work. PLUS they reveal how Grammarly’s 40M+ daily users already rely on email—and why this deal is the key to building the ultimate communication assistant. Don’t miss this deep dive into one of the most exciting AI acquisitions yet!

#AI #Startups #Productivity #Grammarly #Superhuman #VentureCapital #MergersAndAcquisitions

Timestamps:

(0:00) Introduction to the future of robotics and AI regulation(1:11) Introduction of hosts and overview of today's topics(4:19) Cloudflare's new pay per crawl product

(09:37) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today!(10:41) Polymarket segment on Apple's acquisition prospects(14:29) Grammarly and Superhuman CEOs interviews

(19:42) Retool - Visit https://www.retool.com/twist and try it out today.(24:09) AI in productivity tools and email agents discussion(29:23) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/credits(30:46) Grammarly's AI platform and the acquisition of Superhuman(41:16) Introduction of Manu Sharma from Labelbox(41:47) The role of data labeling in AI and Labelbox's data factory(53:44) Labelbox's market position and capital efficiency post-ChatGPT(1:03:00) Advances in humanoid robotics with Jeff Cardenas from Apptronik(1:07:09) Market readiness and capabilities of Apollo 2 robots(1:13:27) Humanoid robotics: Google DeepMind partnership and international competition(1:20:54) US federal support for R&D in robotics(1:22:10) The evolution of humanoid robotics and Apptronik's growth in Austin

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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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Transcript

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0:00.0	So I think the days of hard coding something to pick up a box, those days are over, right?
0:05.4	So we have reached this inflection point, not just in humanoid robotics, but in robotics
0:11.2	as a whole to where it's very clear that learning is going to be the future.
0:16.4	This Week in Startups is brought to you by Northwest Registered Agent. Starting your business
0:22.2	should be simple. With Northwest Registered Agent, you can form your entire business identity in just
0:27.4	10 clicks and 10 minutes. From LLCs to trademarks, domains to custom websites, they've got you
0:33.9	covered. Get more privacy, more options, and more done.
0:41.8	Visit northwest registered agent.com slash twist today.
0:43.2	Retool.
0:49.3	Bridge the gap between AI demos and business impact with technology that's designed for developers and built for the enterprise.
0:51.6	Visit retool.com slash twist and try it out today. And AWS Activate.
0:59.0	AWS Activate helps startups bring their ideas to life. Whether you're just launching or already
1:04.6	funded, apply to AWS Activate today and receive up to $100,000 in credits. Visit aWS.m. Amazon.com slash startups
1:15.2	slash credits. Hello and welcome back to this week in startups. My name is Alex. I'm joined
1:20.8	today by my co-host, Lon Harris. Lon, how you doing? Great to be here. How exciting. I'm very excited, but there is a lot of news today.
1:29.3	We are going to have in a little bit the CEOs of both Grammarly and Superhuman to talk through
1:34.3	their enormous deal, the implications of it, what they're working towards, why the deal came
1:39.3	together, how it came together, so much to get through.
1:42.3	But, Lawn, first, there's a couple of news items we absolutely have to touch on.
1:45.8	The first thing that I want to double-click on for folks is that we've talked about
1:50.0	AI regulation here on the show quite a lot.
1:52.7	There was a push in the House and Senate to perhaps limit state-level AI regulation.
	...

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