Grammarly is now Superhuman! CEO Shishir Mehrotra explains the rebrand | E2201
This Week in Startups
Jason Calacanis
4.4 • 1.3K Ratings
🗓️ 30 October 2025
⏱️ 99 minutes
🧾️ Download transcript
Summary
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, Superhuman Go, digging into their new agent-centered strategy, looking ahead at the potential for AI job displacement, and more.
Jason and Alex also talk about our new nuclear deal with Westinghouse and Japan, OpenAI’s conversion and what it means for Microsoft, 1x’s tele-operated Neo-bot for chores, and much more!
Timestamps:
(00:07:56) Jason is headed to Tokyo, and NOT just for skiing this time!
(10:00) Uber AI Solutions**:** Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at Uber.com/twist
(00:12:21) Untangling this US government-Japan-Westinghouse deal for nuclear power… and why nuclear power is SO important
(20:00)DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to https://www.DevStats.com/twist
(00:20:04) Why Jason says sabbaticals and 4 day work weeks are for established brands, not startups
(30:00) Perspective AI: Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist.
(00:33:01) Will income inequality become a concern, even for the wealthy? Jason says YES.
(00:37:29) Shishir Mehrotra from Gram— NO WAIT, Superhuman! joins us to talk name changes
(00:38:16) Using Grammarly as a model for the new AI assistant, Superhuman Go.
(01:08:39) Nvidia shot past $5 TRILLION in value… How is no one freaked out about this?!
(01:14:52) OpenAI executed their conversion… but Jason says “public benefit corporation” status is pretty meaningless
(01:25:02) Checking out the Neo robot from 1x… he wants to help you with chores and he’s for sale!
(01:32:09) Uber’s speeding up its self-driving plans
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Thank you to our partners:
Perspective AI - Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist.
DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to https://www.DevStats.com/twist
Uber AI Solutions: Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at Uber.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
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Transcript
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| 0:00.0 | I want to bring up something else, Jason, that's a little bit off from where we just were |
| 0:03.4 | on the energy side of things. Instead, to talk about humans. There's been a theme on the show for ever since I got here that companies are either not hiring or reducing their team sizes. And so when we think about taking care of employees, we don't talk about attrition that much. It's just not the thing we're kind of tuning for, I think, as an industry. But our |
| 0:22.6 | friends over at 37 Signals, DHH and Jason Freed, are talking today quite a lot about their use |
| 0:27.8 | of sabbaticals. This is a six-week break for workers in their third year at the company as part |
| 0:33.5 | of their overall kind set up for their staff,, including four day work weeks from May through September. |
| 0:40.4 | And this struck me as just out of the blue, |
| 0:42.9 | because we're talking about laying off 14,000 people at Amazon, |
| 0:45.5 | not trying to keep people. |
| 0:46.4 | So one, are you in favor of sabbaticals of this type? |
| 0:49.4 | And two, are they just drinking different Kool-Aid |
| 0:52.1 | than everyone else? So they are a highly profitable software company that has existed for a long time with a loyal base of users. |
| 1:02.0 | And it is pretty reliable that those revenue streams. People who use base cam, they just love it. |
| 1:10.0 | They're never going to stop using it. |
| 1:11.3 | Okay, period. |
| 1:11.9 | Full stop. |
| 1:12.7 | So when you start a company and you don't have a bunch of investors, which they don't, |
| 1:17.0 | I think they bought out Bezos, who was their only investor back in the day, they can build |
| 1:23.8 | the world they want to live in. |
| 1:26.3 | Now, you remember, they had a whole DEI woke thing happen |
| 1:33.1 | at their company where people wanted to bring all their opinions to work and debate it on Slack, |
| 1:38.2 | just like at Coinbase. And we had this sort of pendulum swing the other way. Hey, if you're at Coinbase, |
| 1:42.6 | you're here to do one thing, you know, provide crypto solutions to the world. If you're at 37 signals, they took a similar approach. Hey, if you want to be here, you're here to make great productivity software full stop, and that's it. And then here's an incredible pay package. And then both companies just said, hey, if you want to opt out, we get it. So during that culture war, which we forget |
... |
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