Flying Cars, OpenAI Spies, Why AI Isn’t Sticking (Superhuman CEO)
This Week in Startups
October 17, 2026
This Week In Startups is made possible by: Today’s show: Today’s college grads are showing up to work at Jason’s company unable to write three sentences. He’s asking what Shishir Mehrotra of Superhuman, the company behind Grammarly, can do to fix that.
Speakers Jason Calacanis, Lon Harris, Shishir Mehrotra, Keith Perez
TopicsTechnology
Jason Calacanis (0:00)
All right, everybody, welcome back. As you can see from my background, I'm back in the saddle. I'm back in Austin, Texas, and the weather, Lon, is perfect. This is the perfect weather. It's been like beautiful, 80 degrees, 75, 85 degrees on the ranch. I threw some Wi-Fi up on the horse pitch. I got a table outside, and I've been trying to get through my jet lag.
But yeah, I just had a really productive trip in Japan for two weeks, and I'm ready to get back to the regular schedule, everybody. I was taping episodes at all times. You know what I always like to do if we're this busy is I got to keep my plot with me. Cut my plot with me on the back of my phone. I'm walking around Tokyo. Man, I had some days, Lon, I walked six, seven miles.
Lon Harris (0:48)
Walk a lot.
Jason Calacanis (0:49)
Do a lot.
Lon Harris (0:50)
There's trains, but then you get to the neighborhoods and you just want to mill around and go down all the little side streets and see everything there is to see. You can't see it all.
Jason Calacanis (0:57)
Yeah. If you're an old man like me and you get addicted to rocking, you throw the backpack on, you walk around, bang, bang. I hit two different lunch places, bang, bang. Two different cafes. I take my laptop out. I work for an hour or two, go to the next place. I just had a wonderful time, visited every neighborhood. I went to the book district, the used book district. I went to the restaurant district.
I mean, I just went to each of the different districts. I have my wife with me. We had a wonderful time, stayed at an incredible hotel, the new Janu Hotel in Azubu Dai Hills. Absolutely the most money I've ever spent on a hotel.
Lon Harris (1:35)
That's where the swells live in Tokyo. That's like the hot neighborhood is in Azubu Dai. I heard about that when I was there.
SPEAKER_4 (1:40)
Wait, wait, who's the swells?
Lon Harris (1:41)
You know, the elite, the 1%.
Jason Calacanis (1:44)
It is the elite area. Yeah, it is the 1% area, and they have a 1% hotel, I can tell you that. But we've got a lot to get to, and I just want to make sure I don't miss a moment. So I'm going to take my blood on the back of my new iPhone 18 I got off the air because I needed a good photo. Take photos of ramen.
The air wasn't taking good photos of ramen. I just pressed the button, boom, and now I'm in record mode. Put it right on the table in front of me. I got all my notes. We use it for the notes for This Week in Startups.
Lon Harris (2:10)
We do. You can see I've got mine on right here. Any kind of conversation, interview, meeting, call, interaction you want to hang on to for later, you just press the button, save it. It's on your desktop, it's on your phone, wherever you need it. If you want to check out Plod, go to plodai.twist and use the code TWIST, and they're going to give you 10 percent off your Plod Note Fit.
Jason Calacanis (2:30)
There it is. All the transcripts come in. I've got a lot of people asking me which one should I get. I always just tell people get the two pros. Just buy both pros because they both sync automatically. You got it for two different situations.
The one that goes on the back for meetings is just awesome. Also, you can record phone calls without having to invoke another piece of software crash a computer. You just have it on the back and it records it. I don't know how it does it with technology. Of course, make sure you are letting folks know, may I record the call as we say in the business these days. May I record the call?
Lon Harris (3:05)
Yes.
Jason Calacanis (3:05)
It's always a good thing to do. Applauds the best.
Lon Harris (3:08)
There it is. It's important.
Jason Calacanis (3:08)
One press, record, and then you get the pin as well. Hey, our guest is here. Let's introduce our guest and get to work.
Lon Harris (3:14)
Once again, joined by the great Shishir Mehrotra, he's the CEO of Superhuman. They of course make AI tools including Grammarly that help you write your documents, manage your email, get work done anywhere that you are, any site that you're on, any platform that you're using, you could fall back on these amazing productivity tools from Superhuman. Shishir, thanks for joining us.
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