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Luba Yudasina$13 Billion CEO Thinks Most People Shouldn't Start A Company
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Transcript
80 min read · 16,259 words- 0:00 – 1:07
Trailer
- SMShishir Mehrotra
People think that Grammarly is about grammar, but it's actually not. It's a much bigger product and business than people think. It's tens of millions of daily active users. You know, it was over $700 million in revenue. When you have a great idea, you should be obsessed with getting that to the world the fastest way possible. I mean, I see lots of entrepreneurs like that. They get very obsessed about ownership, about control, and I think that mindset will lead you astray.
- LYLuba Yudasina
This was Shishir Mehrotra. He's the CEO of Superhuman, the company formerly known as Grammarly. Before that, he founded Coda and sold it to Grammarly. And at YouTube, he built skippable ads, a product that went from zero to $1 billion in 18 months. He also sits on the board of Spotify and Walmart. In this episode, we covered his philosophy on building and why he believes most people should not start a company.
- SMShishir Mehrotra
Sometimes people come to me and they say, "I wanna start a company." And I'll say, "What's the idea that you're obsessed with?" And they don't have one. I say, "That doesn't make any sense to me." And if your level of attachment to that idea is weak, the world will knock you off the idea. I don't think people should start companies in a pressure cooker. [upbeat music]
- LYLuba Yudasina
Shishir,
- 1:07 – 1:32
Shishir Mehrotra, CEO, Superhuman
- LYLuba Yudasina
thank you so much for coming on the show.
- SMShishir Mehrotra
Thanks for having me. Fun, fun way to do, uh, to do a podcast.
- LYLuba Yudasina
Yeah, exactly. We're getting some steps in.
- SMShishir Mehrotra
Yeah.
- LYLuba Yudasina
There's so much to cover and talk about. I wanna get into YouTube, writing, rituals, obviously Grammarly, Superhuman.
- SMShishir Mehrotra
Yeah.
- LYLuba Yudasina
But I wanna get started with a fun fact I heard about you.
- SMShishir Mehrotra
Okay.
- LYLuba Yudasina
You and your daughters are obsessed with Lego.
- SMShishir Mehrotra
Yeah. [laughs]
- LYLuba Yudasina
Can you tell me a bit more about that and the Lego competitions you guys go to?
- SMShishir Mehrotra
Yeah. We
- 1:32 – 8:59
Making the Lego robotics world championships four times with his daughters
- SMShishir Mehrotra
started, um... Uh, we did, uh, we did Lego robotics for seven years. Started when the girls were in middle school. They're now... One's in college, one's a senior in high school. Um, so they've moved on to the next level of competitions. But yeah, Lego robotics runs these amazing competitions. Uh, the rules are basically there's, uh, 15 tasks. Uh, you can use any- anything you can build with Legos, and you have two and a half minutes to solve the tasks. And, uh, we made world championships four out of seven years. Um-
- LYLuba Yudasina
Damn, okay. Wait, how big is the team?
- SMShishir Mehrotra
It varied. Every year was different, but between two and four girls, two and five girls. Yeah.
- LYLuba Yudasina
So very small.
- SMShishir Mehrotra
Yeah, yeah, yeah.
- LYLuba Yudasina
Wow. Were you the coach?
- SMShishir Mehrotra
Yeah, I was the coach. Yeah. It's a very, like... As you get older, the, the s- the school does it.
- LYLuba Yudasina
Yeah.
- SMShishir Mehrotra
But at that age, a parent has to do it. So it's, uh-
- LYLuba Yudasina
Wow.
- SMShishir Mehrotra
Yeah, it was super fun. It's a highly recommended way to, you know, uh, to have fun with your kids, to, to learn a lot about robotics, about building. They learn a lot about teamwork. It's, it's awesome.
- LYLuba Yudasina
That's amazing.
- SMShishir Mehrotra
Very good program.
- LYLuba Yudasina
So how often did you have to coach them to be as-
- SMShishir Mehrotra
[laughs]
- LYLuba Yudasina
... exceptional as, you know, being in the world competition four out of seven times?
- SMShishir Mehrotra
Oh. I mean, I think they would say, um, more, more than they would've liked. [laughs]
- LYLuba Yudasina
[laughs]
- SMShishir Mehrotra
We, we were, we were a pretty Lego-obsessed house. So the, uh, the garage is full of Lego still. There's, um-
- LYLuba Yudasina
Wow.
- SMShishir Mehrotra
Yeah. We've built everything you can imagine. You know, I think officially a couple days a week, but we pretty much worked on it every day. Yeah.
- LYLuba Yudasina
Were you the one who was like, "Okay, girls, we're- I'm gonna get you into Lego," or was it-
- SMShishir Mehrotra
No. My older daughter's friend did it, and she got her in. And then that, uh, that k- uh, that kid, um, aged out of the program and the dad handed it off to me.
- LYLuba Yudasina
Very cool.
- SMShishir Mehrotra
So... Yeah. It was super fun.
- LYLuba Yudasina
Any, any parallels of what you've learned-
- SMShishir Mehrotra
Oh my gosh, so many
- LYLuba Yudasina
... in Lego- [laughs]
- SMShishir Mehrotra
So many
- LYLuba Yudasina
... to building companies?
- 8:59 – 12:18
His dad only paid for majors where the books are 50 years old
- SMShishir Mehrotra
paying for college if you major in something where the books are at least 50 years old."
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
And his-
- LYLuba Yudasina
'Cause CS changes so much
- SMShishir Mehrotra
... his, his view was, uh, CS changes, um, too fast and it's like it's too vocational, and so it's, like, not worth the, not worth the education. He was a physics major.
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
Um, and so that was his, you know... And I, I think he was right, so in his head I was a math major first, CS major second. I think officially I was a CS major first, math second.
- LYLuba Yudasina
[laughs]
- SMShishir Mehrotra
But doesn't really matter. Um, but-
- LYLuba Yudasina
So is this something you are telling your daughters, that they can't major in something where the books are-
- SMShishir Mehrotra
I mean, I, I... This was-
- LYLuba Yudasina
... less than 50 years old? [laughs]
- SMShishir Mehrotra
... this was definitely... I mean, my, my daughter's a math major.
- LYLuba Yudasina
Okay, okay.
- SMShishir Mehrotra
Um, so I mean, I think whether because of that advice or not, she definitely is following that path. Um, and she is actually a, they, they, she's at Princeton, they don't allow double majors.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
So she's, she is math first, CS second. Um, we'll see what the second one does. But I, I think the philosophy of there are some things you learn that are very fundamental, and they really... It's not really the math that matters, it's the learning how to think that matters. Um, and I do think, you know, some of these deeper subjects just force you to get... You k- you keep peeling an onion back of, like, how do they discover the next level-
- LYLuba Yudasina
Yeah
- SMShishir Mehrotra
... of this and the next level of this. You, you learn how concepts fit together. Um, so I, I do think that's pretty helpful, and I guided my kids that way. Yeah.
- LYLuba Yudasina
So let's jump back to you going to college. You went to MIT, a double ma- major, math, computer science. You then start a company out of MIT.
- SMShishir Mehrotra
Mm-hmm.
- LYLuba Yudasina
How did you get startup pilled back in the beginning-
- SMShishir Mehrotra
[laughs]
- LYLuba Yudasina
... of 2000s?
- SMShishir Mehrotra
Well, I, I got forced into it. My, um, I was, uh, a friend and I, uh, started grad school, and so, and we picked a project and we were working on it together. And he came and he said, "Do you know there's this entrepreneurship competition at MIT? Maybe we should, maybe we should apply. Um, it's called the MIT Entrepreneurship Competition." The, uh, it was called, at the time it was called the 50K Challenge.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
'Cause the prize was $50,000. Now it's $100,000, so it's-
- LYLuba Yudasina
Nice
- SMShishir Mehrotra
... I guess-
- LYLuba Yudasina
Inflation.
- 12:18 – 14:47
Why most people should not start a company
- LYLuba Yudasina
you know-
- SMShishir Mehrotra
Oh, I-
- LYLuba Yudasina
... your curiosity and let's see where that goes?
- SMShishir Mehrotra
I, this I have a fairly strong opinion on for startups, and not everybody's gonna like this, but I don't think, I don't think people-
- LYLuba Yudasina
Hot take
- SMShishir Mehrotra
... I don't think people should start companies in a, in a pressure cooker. So I think it's, sometimes people come to me and they say, "I wanna start a company," and I'll say, "What should, what's the idea that you're obsessed with?" And they don't have one. And I say, "That doesn't make any sense to me."
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
Like, starting a company in my mind-
- LYLuba Yudasina
To start a company, yeah
- SMShishir Mehrotra
... yeah, in my mind, starting a company is, it's the, it's often the most painful way to get your idea to the world. Like, to start from scratch is, like-
- LYLuba Yudasina
Mm
- SMShishir Mehrotra
... the hardest way to do it. If you have a thing you really wanna see different in the world, you really wanna work on, there's often, you know, many cases there's easier ways to do it. So you should start a company almost out of, like... I almost view it as, like, a curse.
- LYLuba Yudasina
Yeah.
- SMShishir Mehrotra
It's like, I just can't get the idea out of my head, so I must start this company. Um, but I think, I think that, you know, everybody has a different way of doing it. But I've seen a lot of people who start with this frame of, you know, "I'm starting a company. I don't know what I wanna do," and they end up going in circles. They, th- there's a lot of bad incentives involved in the, you know, the adverse selection of I have to start a company, and therefore every idea is viewed through that lens, instead of, like, what's the most effective way to get this thing done in the world? So I, I think it's better that the startup thing will, will strike you. Th- think curse rather than blessing is the right way to think about it.
- LYLuba Yudasina
What happens if a startup idea strikes you, but then after a year or maybe longer at it, you just figure out that maybe, you know, there's no market, you gotta pivot. Do you get-
- SMShishir Mehrotra
Mm
- LYLuba Yudasina
... do you hope that you get the same level of inspiration for a different idea, or-
- SMShishir Mehrotra
I mean, it's part of the reason why I say it, is because every startup idea hits roadblocks. So if your, if your level of, of, if, if your level of attachment to that idea-
- LYLuba Yudasina
Mm
- SMShishir Mehrotra
... is, is weak, the world will knock you off the idea.
- LYLuba Yudasina
100%.
- SMShishir Mehrotra
Like, there is no such thing as an idea that people haven't thought about, haven't gone after. Like, so you have to be willing to stick through the hard moment of, you know, the customer who doesn't think it's a good idea, or the investor who doesn't think it's a good idea, or the, the, the employee-
- LYLuba Yudasina
Mm
- SMShishir Mehrotra
... doesn't think it's a good idea. Or you hit some roadblock, and, like, if you're really passionate about it you'll go past that.
- LYLuba Yudasina
Yeah.
- SMShishir Mehrotra
But if not, and all you're in it for is, "I just wanted to be"-
- LYLuba Yudasina
A startup founder
- SMShishir Mehrotra
... "a star- a startup founder," then you'll, like, very quickly you'll pivot ideas way too fast.
- LYLuba Yudasina
Yeah.
- SMShishir Mehrotra
Um, and not, not stick through them long enough to see them work. And most interesting things take real time, and so you have to, you have to be willing to stick through it.
- 14:47 – 20:15
The Vinod Khosla email that moved $500,000 in one afternoon
- LYLuba Yudasina
as you said, the world's gonna knock you o-
- SMShishir Mehrotra
Yeah
- LYLuba Yudasina
... over.
- SMShishir Mehrotra
Yeah.
- LYLuba Yudasina
So you started this company. You raised from Vinod Khosla.
- SMShishir Mehrotra
Uh-huh.
- LYLuba Yudasina
What did you learn from Vinod back then?
- SMShishir Mehrotra
Oh, man. Vinod's his own character. I mean, that was, uh... The whole experience of raising from Vinod, maybe its own fun story because he, um, we were basically, we're, we're starting this company. Um, I was trying to raise capital from West Coast investors. At the time, the world was very divided. There was Boston investors-
- LYLuba Yudasina
Mm
- SMShishir Mehrotra
... or East Coast investors and West Coast investors. Very different viewpoints on the world. Um, the, uh... And I kept, uh, I, I'd, I'd flown out to California a bunch of times, but we hadn't really... Lots of interest, but nobody had really bit. And so I'd given up on it, was about to sign a term sheet. Uh, or sorry, I had signed a term sheet with this investor in, um, in Boston. And I get this, uh... But that person hadn't wired money yet, which is an interesting part of the story. And I get this email from Vinod Khosla, and you have to remember, this is 1999, early 2000, um, and so the, the, um, the world is not as connected. So I get this email from Vinod Khosla, but I don't know who Vinod is. And the email, if anybody's gotten an email from Vinod, it's, like, all lowercase, many misspellings. It's, like, not... It, it didn't seem official. And, uh, but he seemed very interested. He's like, "I saw the business plan from this friend. Um, yeah, I'd be really interested in participating." Um, and so I sent it to this, this investor who had, I had signed this term sheet with, and I said, um, "Do you think this is real? What do you think it is? Who's Vinod?" And-
- LYLuba Yudasina
[laughs]
- SMShishir Mehrotra
... so he, he calls me right away and he says, uh, "You don't know who Vinod Khosla is?" And I said, "No, I, I, I don't." And he says, "Well, hang up and walk down the, the street to the bookstore." There were still bookstores.
- LYLuba Yudasina
Uh-huh. [laughs]
- SMShishir Mehrotra
Um, "Look at the rack of magazines." There were still magazines. "The guy whose face is on all the covers, that's Vinod Khosla."
- LYLuba Yudasina
Wow.
- SMShishir Mehrotra
"Go read about him and then call me back." And so I go and I, like, learn a little bit about Vinod, and I come back and I, and as I'm walking back into, to my, uh, to my door in my living group, the, um, my, my CFO, who was my friend-
- LYLuba Yudasina
[laughs]
- SMShishir Mehrotra
He stops me in the hall. He says, "Shishir, it's kinda weird, but $500,000 just showed up in the account."
- LYLuba Yudasina
Wow.
- SMShishir Mehrotra
And what I realized [laughs] was, like, Vinod even signaling interest had completely changed the market around the company.
- LYLuba Yudasina
That's awesome.
- SMShishir Mehrotra
Um, and so anyways, it was, it was a, it was-
- LYLuba Yudasina
So it was those people who weren't wi- wiring money.
- SMShishir Mehrotra
They, they were hadn't wired money. But yeah, it was, I mean, Vinod was, um, I mean, he was at the very top of his game at the time, and, uh, not that he's not now. Um, and I mean, I learned lots of things from Vinod. I mean, Vinod is definitely a, uh, he's a very think big entre- uh, uh, investor. Uh, you know, the bigger the idea, the more interested he is. Uh, he's incredibly fast-acting, fast decision-making, maybe to a fault.
- LYLuba Yudasina
Yeah.
- SMShishir Mehrotra
I think sometimes he, you know, if you had to give him feedback, sometimes he can spin things around a little bit. Um, but it was a great introduction to... And it was definitely the vibe of West Coast capital versus East Coast capital. I mean, it was, it could not have been more different. And by, and by the way, one of his requirements was you gotta move the whole company to-
- LYLuba Yudasina
Mm
- SMShishir Mehrotra
... to, uh, Silicon Valley. So that's why I moved. So we moved and basically he, he sent this email on a Sunday. I met him on Tuesday.
- LYLuba Yudasina
Wow.
- SMShishir Mehrotra
Term sheet signed on Thursday. We got a moving truck the next Saturday, and we were all moving.
- 20:15 – 25:50
Joining YouTube when it lost money on every view
- LYLuba Yudasina
YouTube when it was literally just purchased by Google, and it sounded like YouTube was l-losing over a billion dollars a year.
- SMShishir Mehrotra
Almost a billion.
- LYLuba Yudasina
Something like that. Almost a billion dollars a year.
- SMShishir Mehrotra
Not quite. We never quite got to a billion.
- LYLuba Yudasina
A lot of money. [laughs]
- SMShishir Mehrotra
Yeah. Yeah.
- LYLuba Yudasina
And it was kind of seen as Google's big mistake.
- SMShishir Mehrotra
Yeah.
- LYLuba Yudasina
So you join. What was it like working on a business that had such bad perception internally?
- SMShishir Mehrotra
Well, I mean, it's, it was interesting because it was, it was definitely the exception, right? You know, Google had bought a number of companies, uh, and almost all of them were turning out to be reasonable successes, and YouTube was the w- the odd one.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
And like you said, it was, we were losing, uh, not only we were losing hundreds of millions of dollars a year, we were, uh, net negative on every single view. And so it meant that the more views we had, the worse the business did.
- LYLuba Yudasina
Wow.
- SMShishir Mehrotra
Not a great spot. Uh, we had this billion-dollar lawsuit, uh, from Viacom. We were known for, like, uh, things that people didn't quite understand, you know, grainy videos of cats-
- LYLuba Yudasina
Yeah. [laughs]
- SMShishir Mehrotra
... and that they... And so people just didn't understand why, why is it important? Where does it fit in the world? Our number one competitor at the time was a company called MySpace-
- LYLuba Yudasina
Yeah
- SMShishir Mehrotra
... which I think people nowadays probably don't even remember. Um, but I, I don't think people really saw us in that frame. But there was a small group of people who saw YouTube differently, and that group excitedly ran to it and said, "I bet we can turn this into a very different kind of, uh-
- LYLuba Yudasina
Who was in that group?
- SMShishir Mehrotra
You know, I think I, I went over the same day as my boss, a guy named Salar Kamangar, um, who was employee number seven or something at Google, and he was a sponsor of the original acquisition and, and so on. There was a, there was a group of product leaders, um, actually the one here, uh, Noam Levinsky. We bought his company and he joined. Um, uh, he's my, uh, chief product officer here at Superhuman. Um-
- LYLuba Yudasina
What company was he running that you bought?
- SMShishir Mehrotra
A company called Episodic.
- LYLuba Yudasina
Got it.
- SMShishir Mehrotra
Um, the, um, there was a number of them that, uh, you know, many of them are spread around the industry, although a number of them work, work with me here at Superhuman as well. Um, but I, you know, I often describe this, this phase as you can, you can see team dynamics that are either you're more pirate or more navy. This is definitely pirate.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
So this is definitely, you know, in that same entrepreneurial spirit. You know, the world thinks is i- isn't gonna work, and for some people, that deflates you, and for some people that, that really, um, powers you. And so that was, that was our frame. And we just had a viewpoint, it wasn't really that complicated a viewpoint, um, that... You know, I remember the first time I said it publicly was I went, I joined, and I think a month later, I had to give a talk at this big ads conference. And, um, so I gave this line, I said, uh, "YouTube is gonna do to cable what cable did to broadcast." And we went from, you know, three channels to 300 channels to, uh, and now I think we're headed towards millions of channels. And honestly, like, that room of people almost laughed out loud. They, like, didn't understand. It seemed so crazy to them that this site that was mostly, you know, what felt like joke and cat videos, and it didn't feel serious, was gonna compete with cable television. And they had all stuck us in, you know, oh, it's a video social network. That's how they, they perceived us. Um, but that was our viewpoint, was that, you know, YouTube was gonna do to cable what cable did to broadcast. It was a fairly simple idea, and it drove-
- LYLuba Yudasina
Yeah
- SMShishir Mehrotra
... everything about how we thought about it. If you thought about it that way, then you were very motivated to get past every roadblock and get to that next step. And, you know, the pirates ended up, it ended up working. So.
- LYLuba Yudasina
That's incredible.
- SMShishir Mehrotra
Yeah.
- 25:50 – 35:20
Board meetings with Eric Schmidt about shutting YouTube down
- SMShishir Mehrotra
existential. Every, every, we had a, a quarterly board meeting with the, with, uh, like the, the CEO of Google, Eric Schmidt, the CFO, and a few of the other executives, and basically every board meeting was, "Should we shut this thing down?"
- LYLuba Yudasina
Yeah.
- SMShishir Mehrotra
"Should we sell it to someone else?" So you felt enormous pressure to deliver. You also feel this, especially once an idea gets to that stage, you feel this, this, um, uh, responsibility of, you know, we were already at the point of, you know, millions of creators using it-
- LYLuba Yudasina
Mm
- SMShishir Mehrotra
... and millions of users using it. The business was not very good. And so it was quite possible that it's, like, a very useful service but a terrible business.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
And gosh, it would've really sucked if we had hung up our hats and said, "That's it. We're not gonna do it." And so you feel like this propulsion. I sort of remember I had this, um, I went on this, uh, plane ride. I was flying to New York, and I sit down next to this woman and, uh, and um, we're just introducing ourselves and I said, "What do you do?" And she says, "I work on YouTube." And YouTube at the time was like 150 people. I knew every person who worked on YouTube. She definitely did not work on YouTube.
- LYLuba Yudasina
[laughs]
- SMShishir Mehrotra
And I said, "Really? What do you do?" And she's like, "No, no, no, no, no. I'm a YouTube creator."
- LYLuba Yudasina
[laughs]
- SMShishir Mehrotra
"YouTube sends me my checks, so I just say I work on YouTube." And it was like, it really stuck with me, and she gave me her business card, and her business card said YouTube on it.
- LYLuba Yudasina
[laughs]
- SMShishir Mehrotra
[laughs] And, and had her, had her channel. And it was just a good reminder of, like, you're doing this thing-
- LYLuba Yudasina
There are real people who are making a living
- SMShishir Mehrotra
... and there's, yeah, there's real, there's, there's a real, there was a real ecosystem being created out of it. And so, like, you have this stress of, like, your stress is driven by... It's usually not, it's not selfish. It's not personal. It's all, like, you know, it's your employees, it's your customers, and in this case, it was our creators, so that you're, you were giving them this chance to, to have a, a, a voice in the world. And for many of them it was, like, completely heartwarming stories-
- LYLuba Yudasina
Yeah
- SMShishir Mehrotra
... of how, how they, how they did it. And so, yeah, enormous stress. You show up, and every mistake you made was like, the cost was not just, "Oh man, I'll go get another job." Like, it was, "This thing is not gonna exist." And so, yeah, I mean, I, I think I thrive on stress, so it's not, it's okay, but I would describe it as quite stressful.
- LYLuba Yudasina
Tell me more about the statement of you thrive on stress.
- SMShishir Mehrotra
I thrive on stress. Um, I think that for me, that kind of stress brings out creativity. It brings out... Like, I think when the stakes are high, I, I, I feel more energy. Um, but it doesn't mean you're not, like, you know, you have, you have that queasy feeling in your stomach.
- LYLuba Yudasina
Yeah.
- SMShishir Mehrotra
You have trouble sleeping. Like-
- LYLuba Yudasina
Mm
- SMShishir Mehrotra
... you have all those things, but you're also, like, up at the whiteboard drawing an idea.
- LYLuba Yudasina
You're obsessed with making it work.
- SMShishir Mehrotra
Yeah. Yeah. And so, like, in my mind, there was a, there was a small period, and for the most part, I've, I, I think I've worked on seven jobs in my career, but they, I had, like, a, and basically taken no breaks except for after YouTube to Coda.
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
And I took a six-month break, and it was, like, the worst six months of my life.
- LYLuba Yudasina
[laughs]
- SMShishir Mehrotra
It was like I just didn't have-
- LYLuba Yudasina
[laughs]
- 35:20 – 40:30
The skip button that went from $0 to $1B in 18 months
- SMShishir Mehrotra
five things on it.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
And the, um... I mean, actually, interestingly, one of the things on that list, there was a bunch that some were personal, some were... But there was one on that list which was we hadn't yet s- uh, shipped the thing that I thought we were gonna... Like, when I joined YouTube, part of the reason I joined was I had this idea for a different way to think about monetization on, on-
- LYLuba Yudasina
Was it skippable ads?
- SMShishir Mehrotra
... the skippable ads. And so the... And this was two years later and we hadn't shipped it. And I felt very confident that if I left, it wouldn't happen, and I felt fairly confident that if it didn't happen on YouTube, it wouldn't happen on any, on any property. Um, and for me, that felt like a travesty. It felt like-
- LYLuba Yudasina
Mm
- SMShishir Mehrotra
... you know, this is, this seems like such a better thing. I know it seems small in, in retrospect, but at the time it really mattered to me. Like, this was idea, I felt like, you know, I would feel really badly. Um, actually-
- LYLuba Yudasina
Why did it matter to you so much?
- SMShishir Mehrotra
I mean, I, I think, I guess I view advertising and marketing as a, as the lubricant of society. And so I think when it's inefficient, people don't find, you know, people don't find the, the... I think a lot of people look at advertising as annoying, and they view it as a, a tax. I think they miss that on the other side of every advertisement is a, is a company trying to introduce you to a product that may matter to you.
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
You know, I think that if that falls apart, the entire market becomes more inefficient and you, you end up with much worse outcomes. But anyway, I, I... Like it mattered to me, I don't know, it just felt, i- even on a visceral level, I thought about it as, you know, if, if, if the, if the skip buttons went away, like would I just feel personally bad?
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
That I, I could have done something about it and I didn't do anything about it. I know, like now I feel like I work on things with much higher purpose than that, but it-
- LYLuba Yudasina
Yeah
- SMShishir Mehrotra
... at the time, it really mattered to me. And so anyways, I... that, that was on my list. It was actually interesting, I left YouTube years later and I was at this dinner party with a group of people that, that don't know much, uh, that are not really in tech, and they didn't, they ne- they've never really understood, like what it means to build one of these products and like what are, what do engineers do, and so on. Didn't really make any sense to them. And they said, "Oh, you're leaving YouTube. Well, that's interesting. What are you gonna do?" And I answered some questions. They said... And they all had the same question for me: "Does that mean the skip button's gonna go away?"
- LYLuba Yudasina
Oh.
- SMShishir Mehrotra
And it was like interesting to me how-
- LYLuba Yudasina
Important
- SMShishir Mehrotra
... how important it was to them that their association with, with, with the product, and I think it was, it, it mattered.
- LYLuba Yudasina
Yeah.
- SMShishir Mehrotra
And so anyways, like Dean, Dean really coached me on how to find marginal purpose, which I think is not an easy thing to find, but when you find it, it's very motivating. Like, here's the thing I really, really wanna have happen-
- LYLuba Yudasina
Yeah
- SMShishir Mehrotra
... that I'm quite convinced that if I weren't focused on it, it wouldn't happen.
- LYLuba Yudasina
And you can probably say that skippable ads is what made ads better, because if your ad sucks, then people are gonna skip it, so-
- SMShishir Mehrotra
I mean, that was the theory, right? So the theory was if you make an ad skippable, and you only charge the advertiser when the ad is, um, not skipped, then you can rebalance the power.
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
And I mean, if you think about like as a, a... I mean, it's all... I thought the idea was very simple because it was basically like the same as Google AdWords, right? Like, what was, what... The AdWords, uh, assumption was, well, if you don't click the ad, then it's not as valuable, and you reset the balance of power and now Google has an incentive to find the right ads and advertisers have an incentive to be more relevant. And, you know, obviously like when Google started, the entire ad market was so much smaller than it is now, and they grew the market because all of a sudden you as a, as a business owner can get people-
- LYLuba Yudasina
Mm-hmm
- SMShishir Mehrotra
... to your products in ways that are very efficient, and it allowed whole new classes of products to exist. And I think that YouTube has done similar thing. I mean, I actually, quite ironically, Grammarly turned out to be one of YouTube's top 10 advertisers.
- LYLuba Yudasina
Oh, wow.
- 40:30 – 45:54
Susan Wojcicki and the 55/45 creator revenue split
- LYLuba Yudasina
on YouTube is-
- SMShishir Mehrotra
Mm-hmm
- LYLuba Yudasina
... what did you learn from late Susan Wojcicki?
- SMShishir Mehrotra
Oh. Susan, um, lots of things. I mean, Susan, so as, as background, Susan's the one who hired me.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
Um, so she was my first boss. Weirdly, this Google TV team reported to her even though she, she handled ads. Um, uh, it wa- ba- basically because she was a pretty good sponsor for these, these Concord, uh, uh, projects. Um, lots of things to learn from Susan, but I think probably the one that is most interesting to me is, um, Susan had a way of thinking about ecosystems that was, it was uplifting. It was... I mean, I think, I, I, if people don't know, she's, I mean, now she's known for, uh, she ended up taking over YouTube and, and, and doing a great job growing YouTube. But the thing she was, at the time, the thing she was famous for was a th- a product called AdSense, uh, which is the ability to put ads on any website and the publisher, the, the owner of the website makes some of the money. So the advertiser pays money, Google makes some, and the, and the, and the, the site hosting the ads makes some. And, um, the idea requires really thinking about an ecosystem with multiple parties and how to create something that isn't a zero-sum game. And many, many people who had gone after markets like that were, um, were motivated by, um, short-term gains, or they couldn't find the right balance of, in that case it was, you know, Google, the publisher and the advertiser, and you had to find a way to balance all their needs. And, you know, for example, it was, it was always hard to manage ad qualities on, on, on those things. And I would argue that as the ad networks have gone past Google, ad quality on those things have really gone downhill. And as you know, we're now subjected to lots of very mediocre quality display ads all over the internet. Um, but it wasn't, like the Google ones didn't feel like that. They, they felt like they were constantly aiming for a balance of what the, what the user wants, what Google wants, publisher wants, what advertiser wants. Um, and so for YouTube, I mean, she was the main, her and Salah were the main sponsors for buying, uh, YouTube, and I think they saw the same promise-
- LYLuba Yudasina
Mm-hmm
- SMShishir Mehrotra
... that this is a, you know, this is a, um, this is not a zero-sum game. I remember going to her when, uh, one of the earliest former decisions we made on YouTube was About a year in, uh, we opened up the YouTube Partner Program.
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
So up till then, we only allowed people... We on- or initially, we only allowed, um, major media companies to monetize their content on, on YouTube. You couldn't, you couldn't run ads on YouTube unless you were a major studio or, or label or so on. And, and o- obviously, the ethos of YouTube, that was completely the opposite of how we wanted to think about things. And the, um, uh... So we had this big debate about it, and we decided we're gonna open up so any creator can apply to be part of this partner program. And, and nowadays, you know, it's a pretty straightforward process of, like, you wanna start a podcast, you can go-
- LYLuba Yudasina
Mm-hmm
- SMShishir Mehrotra
... post on YouTube and make money. Um, and we had a big debate about how to do it, and then there was a big debate about how much revenue to share with the creator. And, and remember at this time, YouTube's losing hundreds of millions of dollars a year.
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
And even though that was the case, we decided to create a revenue share for, uh, for advertisers, like say a 55/45 split. Um-
- LYLuba Yudasina
Why were you guys convinced that that was the right decision?
- SMShishir Mehrotra
Because of this, like, what, what, what Susan described. It's the ecosystem thinking.
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
It was... 'Cause it was like... And I, by the way, it's still the case that I think YouTube is the only major media property, um, that has a publisher-partner revenue share model.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
Like, everything else does it with, with side deals and, you know, with creator funds and so on. Um, the, uh... But I think the way YouTube did it really stood out at the time. And, uh, we ended up turning it into one of the YouTube values. We called it, uh, even playing fields invite play.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
And it was basically this idea that, you know, at the time, the creators coming after YouTube were all, all quite small. Um, but we believed that if we could create an economic model that you could rely on and that we would stand behind, then you would invest. But if we, if we made it arbitrary, if we made it look like a fund that could disappear next year, uh, or worse, if we didn't pay you-
- LYLuba Yudasina
Yeah
- SMShishir Mehrotra
... then, then we would see this race to the bottom-
- LYLuba Yudasina
Mm
- SMShishir Mehrotra
... of what, what, what would happen, um, with, with, uh, content creators. And I think Susan had seen that happen with AdSense and the web, the web market that, you know, I in- I mean, I, ironically, even including YouTube, 'cause YouTube was a big AdSense customer, um, YouTube probably wouldn't have existed without AdSense. And her view on, no, you should share revenue even when it hurts because you're, the, the broader flywheel will, will move, I think she was very good at being willing to stick through an ecosystem like that.
- LYLuba Yudasina
Yeah.
- SMShishir Mehrotra
Yeah.
- LYLuba Yudasina
It's expanding the pie mentality of business.
- SMShishir Mehrotra
Yes, yes.
- 45:54 – 53:52
Sketching Coda on a notepad by his bed
- SMShishir Mehrotra
once I got the idea for Coda in my head, I just couldn't stop thinking about it. I had a little notepad by my bed with all the sketches of what it should look like. I mean, our, our investor pitch was basically just walking through those sketches. It was like, "Here's what we wanna build." Um, and it was interesting because it's not a market where, you know, the idea, the core idea started with the world of, uh, productivity hasn't meaningfully changed in decades. Um, and you know, we still had antiquated metaphors like documents or spread- uh, spreadsheets and presentations are all separate things. And the second, uh, observation was that the way people use productivity tools, the way people use documents, spreadsheets, presentations, is actually like application surfaces, but they just don't call them applications.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
It's how you do planning. It's how you... It's every CRM system starts as a spreadsheet. Every, you know, all of these things were actually what these tools were being used for, but not what they were built for. The market size was really obvious. Like, this is o- it's obviously a category which can support, uh, a large business, and it was... The, all the question was, does somebody have a product idea that, that'll work?
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
And so my, I just got really obsessed with, I think I have a way to do it. I think, I, I think I could picture it, and, you know, we had specced out many elements of it. This is what the surface is gonna look like, and we're gonna rethink the formula language, and here, here's all the different things we can do to make this the, the, um, the doc as powerful as an app. The, the-
- LYLuba Yudasina
And-
- SMShishir Mehrotra
... tagline for Coda
- LYLuba Yudasina
... and take me briefly to that six-month sabbatical.
- SMShishir Mehrotra
Yeah.
- LYLuba Yudasina
Did you get pilled by this idea on the sabbatical? Uh, was it you were forcing yourself to take a break and take a rest for six months, and then you came up with it, or-
- SMShishir Mehrotra
Yeah, so I, I was pretty sure I was gonna end up taking another job at Google, and then, uh, Sundar had just taken over as, as CEO, and he had a bunch of different things he wanted me to do, but I was just taking the time. I s- you know, I'd been working really hard for a while. I'm, I'm gonna go and, um, and explore ideas. I'm gonna relax. I'm gonna travel. Um, all-
- LYLuba Yudasina
You already had kids at that point.
- SMShishir Mehrotra
I had, uh, yeah. They were six and eight.
- LYLuba Yudasina
Okay.
- SMShishir Mehrotra
Yeah.
- LYLuba Yudasina
Like, hang out with my kids.
- SMShishir Mehrotra
Um, yeah. Um, the, the, the, um, they weren't, they weren't in robotics yet, but they, they, um, they were still small. They, um... Anyway, so they, um, I was assuming I was probably gonna end up staying at Google. There's a few other things that people were recruiting me for, all of which look like some version or shape of, of YouTube-like things. And, um, and then I had a friend, uh, this guy Alex and I, who ended up being my co-founder, who's one of the best engineers I've ever worked with, and he was hanging out as a entrepreneur-in-residence at General Catalyst with, with, uh, with Hemant Taneja. And, um, and he had asked for my help in helping him figure out what idea he should work on. So amongst all the other things I was doing, I was helping him brainstorm ideas. And this-
- LYLuba Yudasina
Did you give him the same advice, that you shouldn't be, uh, starting a company-
- SMShishir Mehrotra
Yes
- LYLuba Yudasina
... if you don't have an idea yet? [laughs]
- SMShishir Mehrotra
Yes, yes. He ignored it, but it didn't matter.
- LYLuba Yudasina
[laughs]
- SMShishir Mehrotra
Um, so the, uh, um- He, uh... Anyway, so we started brainstorming ideas, and we started talking about what would eventually become Coda. And I think we both got really excited about it, and it was just a... Once you could picture it, it felt like a really obvious product. We had both worked at Microsoft in the past, and so we'd worked on the Office team and had a pretty good sense of like what- why those products were not evolving-
- LYLuba Yudasina
Mm
- SMShishir Mehrotra
... um, and what even, like, what seems like obvious in retrospect changes, why they were gonna be hard for those, those products to do. And interestingly, I didn't wanna start the company.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
So I, I told him, "You should start this. I'll invest. I'll, I'll help. Um, and if you don't want to do it on your own, I'll help you find the right home for building it." And so I went and talked to everybody. I mean, I told-
- LYLuba Yudasina
Wow
- SMShishir Mehrotra
... Sundar about it. I talked to Satya about it. I talked to, you know, the Dropbox folks, the Box folks, the... Like, every company I could find, I said-
- LYLuba Yudasina
Why didn't you wanna start it?
- 53:52 – 59:30
Why he sold Coda to Grammarly
- LYLuba Yudasina
about that decision to converge with Grammarly.
- SMShishir Mehrotra
Okay.
- LYLuba Yudasina
I know that someone from your board told you-
- SMShishir Mehrotra
Hemant. Yeah.
- LYLuba Yudasina
Yeah.
- SMShishir Mehrotra
Hemant. Yeah.
- LYLuba Yudasina
Yeah, exactly-
- SMShishir Mehrotra
Yeah
- LYLuba Yudasina
... that you need to talk to the founders.
- SMShishir Mehrotra
Yeah.
- LYLuba Yudasina
And from what I've read, it sounded like this very swift decision where you had a strategy around AI productivity, and they had the same strategy. And you were like, "Man, we should combine our strategies because they're the same," and the founders didn't wanna be a CEO.
- SMShishir Mehrotra
Yeah, I mean, I would, I, I would definitely give Hemant a lot of credit for recognizing two groups of people who, in his mind, were headed the same way, but was not obvious to either of them that that was the case.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
And so he had called and told me, "Hey, you should, uh..." I was in the middle of raising our next financing round.
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
And I was about to, about to finish that, and he said, "Hey, before you close anything, why don't you go meet with the Grammarly founders?" And my, my first reaction was, "I'm not sure I get it." Like I, I love Grammarly as a product. I, you know, I, I, I've loved them as a business, but it seems different than what we're working on. And, and he said, "No, you're probably not understanding where they're headed with this product, and you, you guys should spend some time together." So I, um, so I flew up to Vancouver and, uh, spent some time with Max and Alex, the founders of Grammarly. And you know, it- I learned a lot about Grammarly that, you know, and it sounds like you probably read and, and, and seen, but, you know, they, they... First off, it was, it's a much bigger product and business than people think. It's, you know, it was already, uh, tens of millions of daily active users.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
You know, it was over $700 million in revenue. It was a, um, a much more scaled product than people assume.
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
The, um, but the main thing they told me that really stuck with me is people think that Grammarly's about grammar, but it's actually not, and that the core technology was not really about grammar. It was about bringing AI to the edge.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
And the way they described it is, if you picture the product a little bit differently, they say, "Here's a product where, uh, uh, Grammarly sees a million unique applications a day. Every desktop app, mobile app, and web app that you're, that you're in, Grammarly is there, observes what you do, annotates it in a way that's unobtrusive to you and to the application, and then make changes on your behalf." Their view is that Grammarly was the OG agent. It's the original agent. Um, and they described the main-
- LYLuba Yudasina
That's true
- SMShishir Mehrotra
... the main technology of doing it, they described it as the AI superhighway. We built this highway where you could bring AI right to the edge where people work, and in their view of talking about it, there's one big problem. We're only running one car on that highway. It's the one with your grammar teacher in it. And it turns out to be a really valuable car that tens of millions of people choose to use every day, and to spend hundreds of millions of dollars in revenue on. But it's a vast underutilization of this infrastructure. And as they started talking about it, we started realizing where they wanted to head with, uh, with AI was actually very related to a set of ideas we were working on, uh, at Coda. And so that ended up feeling like a, a clear match. They also mentioned that they... You know, there was, there was kind of a, a, a straightforward path for Grammarly. You know, popular product, doing quite well. Just take it public, continue down the normal path. But they felt like this was too big an opportunity to pass up. And to do it, they wanted someone with a bit of a founder's mindset to, to, to run it. And so they, they wanted to buy the company, but they also wanted me to come run the combined company, which was a, um, uh... I mean, I was flattered. It was definitely, uh-
- LYLuba Yudasina
Mm-hmm
- SMShishir Mehrotra
... unexpected. But the, um, but it, it kind of felt like starting a new company. It's like the same test. And it's like, you know, do, what are the goals? What's the margin utility? What's the, what's the purpose? Am I gonna, am I gonna care? And, and, um-
- LYLuba Yudasina
You didn't really feel like you had an exit.
- SMShishir Mehrotra
It, oh, it definitely did not feel like an exit. I mean, I think, I think selling Coda to Grammarly is definitely a, a start, not... Like, I think people say that a lot, a start, not an end. This is by any definition-
- LYLuba Yudasina
[laughs]
- SMShishir Mehrotra
... this is a start, not an end. Um, and, you know, the, the, the mission ahead of us is definitely what I signed up for. Um, the, uh, um... But it was, you know, I just, same thing. I couldn't get it out of my head, as, uh, just seemed like such an obvious idea in retrospect. And, you know, but you look, one fun stat is we do, Grammarly does over 100 billion LLM queries per week.
- 59:30 – 1:01:45
Purpose over ownership and zero startup pride
- LYLuba Yudasina
at all like, "Oh, but I can do it myself at Coda. I've been building this for 11 years. I should continue"? How did you deal with those emotions, if any of those were present?
- SMShishir Mehrotra
I mean, I, I don't, I, I... [sighs] It's sort of back to the, like, I, I don't have any obsession with starting companies. And in my mind, when you have a great idea, you should want to... Y- you should be obsessed with getting that to the world-
- LYLuba Yudasina
Mm-hmm
- SMShishir Mehrotra
... the fastest way possible. And I think people who start that with a vantage point of, "I'm only interested if I-
- LYLuba Yudasina
Mm-hmm
- SMShishir Mehrotra
... own 100% of the company, or if I'm the only founder," or so on, I think they end up in the wrong spot. And, you know, so in, in my career, I feel like, you know, I've started two companies from scratch, and that's Centrada and Coda. But I would say, like, my role with both YouTube and Grammarly, from my perspective, feels like a founder.
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
Like, I, I, I feel like where we were headed was, it just happened to be the best platform to get that, to get that idea done. Um, and I think that has led me to a better spot of don't, don't h- hold... Like, I always tell, um, I get asked by students all the time, they're like, "Oh, I have a list of startup ideas."
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
I said, "Please don't have a list of startup ideas. Just have a list, call it things I'd like to see different in the world, and then be open to the fact that maybe the best place to work on it is in a startup."
- LYLuba Yudasina
Yeah.
- SMShishir Mehrotra
And when the right thing comes along, and this kinda weird-shaped product in YouTube comes along, and that's maybe the right way to change how to think about media, and advertising, and so on. Or when something like Grammarly comes along, and it shifts your viewpoint on a very different kind of AI platform, you have to have the mindset to say, you know, "I'd actually, I don't need, I don't need a sense of ownership. I need a, I need a sense of purpose. I need a sense of accomplishment." Um, and all those things tend to work out, uh, work out well. But I, I don't think I had any- Any of that startup pride. No.
- LYLuba Yudasina
It sounds like the same idea as being attached to outcome versus being excited about the process.
- SMShishir Mehrotra
Yes. Yes. Yeah. I think it's... Too many people get... I, I mean, I see lots of entrepreneurs like that. They get very obsessed about ownership, about control, um, and I think that mindset will lead you astray. It's, uh, um, you do, do what it takes to make that idea happen. But I mean, I think some of my best ideas, I don't... Like, I think they turn into investments, they turn into, like, companies I sh- like, advise. Um, like
- 1:01:45 – 1:04:49
The bundling theory he built with Daniel Ek at Spotify
- SMShishir Mehrotra
I had a whole theory on how I thought bundling should work, that turned into a great relationship with Daniel at Spotify, and, you know, in that case, I didn't have to join the company at all.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
And I still think it's a, uh... I feel like I got a chance to work on seeing this idea turn into something. Um, so have your list of ideas you want to see different in the world, and I think it's... You'll feel a lot of success as they happen if you, if you, if you remove ownership from that, from the equation.
- LYLuba Yudasina
So since you mentioned bundling-
- SMShishir Mehrotra
Mm
- LYLuba Yudasina
... I know you're really passionate about bundling.
- SMShishir Mehrotra
Mm-hmm.
- LYLuba Yudasina
Give me the pitch for bundling in Superhuman.
- SMShishir Mehrotra
Oh. Um, sure. I mean, it's, it, I think Superhuman is one of the easiest pitches. I mean, I think, maybe b- backing up a moment, I think bundling is a topic that is, I think, one of the most misunderstood economic topics out there. There's a, I wrote a paper, uh, maybe a decade ago now called Four Myths of Bundling.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
Um, uh, actually, Daniel a- Daniel from Spotify asked me to write it down after we, we talked about it a bunch of times, and it's called Four Myths of Bundling. The, the paper starts with the story of, uh, the, um, four myths of bundling with a, a person that says all these things about bundling that turn out not to be true, and the person I was picturing was just myself. Like, they were all, they were all things I had said that turned out not to be true. Um, and you know, for example, people think that, um, you know, bundles should be, uh, as, as narrow as possible. Like, you want bundles with only the four very related products. But actually, the-
- LYLuba Yudasina
Like Amazon is a great example of a really broad bundle that works very well.
- SMShishir Mehrotra
Amazon's a good example of a really broad bundle. If you look at, you know, you, you go ask the folks at The New York Times and you say, "What should The New York Times be bundled with?" If you asked any New York Times subscriber, they would say, "Oh, I'd want, I'd want it to be bundled with The Washington Post."
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
Because they share, um, they share some ethos, they share some, uh, uh, um, subscribers and so on, but it's actually the opposite. You, the, the myth number four in the bundling paper is the, um, the best bundle is one that minimizes, uh, super fan overlap and maximizes casual fan overlap. And so the, the idea of how to think about bundles, how to think about subscriptions, I... First, as a, as a, uh, economic and math topic, it's fascinating. And, and, and once you see it, you'll see it everywhere.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
You'll see it, you know, that's why health insurance works. Um, it's honestly why, why government and taxation works. Um, they're all forms of, they're all forms of bundling. The, um... But this core principle of bundling is about bringing together, uh, minimizing super fan overlap, maximizing casual fan overlap. You're bringing together products that themselves have very deep followings, and then using them to build bridges to people that have w- what, what you would think of as casual fanship to those, to those products. Um, and there's a bunch of different examples of that in the, in the world. Obviously Spotify's done a lot of it. And what we're doing at Superhuman is definitely, uh, uh, that pattern. I mean, we're taking products that are beloved in their categories, you know, with, with products like, uh, Superhuman Mail, uh, which is o-
- 1:04:49 – 1:09:37
Superhuman's AI agents and 60% of auto-drafted emails sent
- SMShishir Mehrotra
one of the most beloved, uh, email applications in the world, or products like Coda, which is now Superhuman Docs. It's, I think, the most productive way to run a, run a team in an all-in-one space. Um, you know, we just bought, uh, this company GPTZero, which is the, the number one authenticity company. Of course Grammarly, and, uh, our newest product was Superhuman Go, which is the, the platform layer of Grammarly. Each of them has a distinct promise, a distinct audience, and they have to do a good job of winning that person. But then once you do, you start to see people that say, "Well, if I, if I can get them all together, then I, then I'll prefer to get them as a, as a bundle." Um, and I think that's, you know, bundling playing out. And we just launched the newest version of AI auto drafts, and it's a really hard problem because I think it's one of those things where if it's, it's kinda good but not great, it's actually annoying.
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
It's like, "Don't draft mails for me that aren't good." We just hit a milestone to about, uh, over 60% of mails we auto draft are now sent, with half of them being sent with no changes. Um, and so-
- LYLuba Yudasina
Oh, wow
- SMShishir Mehrotra
... I, I think we're... And even that, I think, I think you want that number to be higher.
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
But it is a, it is a remarkable improvement, uh, from, from where we, from, from what the world generally expects. But in that way, mail stops being the workplace for me to work and starts being the place for me to work with my, in this case we call it the mail agent, um, that's working alongside me. And then as we go forward to where we're headed with Superhuman and with Go, it should become the place for all my agents to work with me.
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
And, uh, you know, to give you an easy example, I want... You know, today that mail auto draft understands everything about me, understands everything about, you know, our correspondence. And so, for example, when it drafts an email between us, it'll follow the tone for how our conversation-
- LYLuba Yudasina
Yeah
- SMShishir Mehrotra
... has, has gone. Um, but as we bring the rest of the agents, it can do things like know what's in our sales system, or know what's in our support system, or read all the documents. You know, I'm, I'm responding to someone and, uh, you know, it says, um, "There's a customer, they had a support issue yesterday, so make sure you say something about that in the, in the email." And all those things happen by- Uh, by being able to bring all those, all what we call agents, but you can think about as virtual teammates-
- LYLuba Yudasina
Yeah
- SMShishir Mehrotra
... into that, into that same experience. So I, I've... They- I think they've actually made amazing progress, especially in the last year. Um, but I think we have a lot more to come there.
- LYLuba Yudasina
Yeah, I think the superpower that comes with AI is the superpower of context. If you can have your AI have context across everything that you work with, then you can truly become superhuman.
- SMShishir Mehrotra
Yes.
- LYLuba Yudasina
But it's that disconnect-
- SMShishir Mehrotra
Yes
- LYLuba Yudasina
... that doesn't allow us to be there just yet, so I'm really excited for it.
- SMShishir Mehrotra
You, you want context, but I think you want, you know, the, we, we, we, the, the, the, the trio is, uh, ubiquity, per- uh, proactivity and, and context. Or we sometimes refer to it as knowledge. But you want this agent that knows everything you know. You want it to actually work where you work, which is, it turns out to be really challenging. And then you want to do it, you want it to do it proactively. You don't wanna have to ask. Most AI systems today, I think context has become more obvious for people of we want AI systems that have read all of our past writing, that have read all of our systems and so on, but the idea that it should take action before I ask and that it should-
- LYLuba Yudasina
Mm
- SMShishir Mehrotra
... be present in the surface where I work is what dramatically uplifts-
- LYLuba Yudasina
Yeah
- SMShishir Mehrotra
... the utility. That's why we-
- LYLuba Yudasina
Is-
- SMShishir Mehrotra
Yeah
- LYLuba Yudasina
... is the surface area challenging because you have to have an open API to the-
- SMShishir Mehrotra
And that's without-
- LYLuba Yudasina
... apps that you're working in for the agent to have context, or is it something else?
- SMShishir Mehrotra
So I mean, the way Grammarly does it and what we're turning into Go is we've built a set of ways to work with basically every different application.
- LYLuba Yudasina
Mm.
- 1:09:37 – 1:15:32
Why AI will make teams bigger
- LYLuba Yudasina
some lessons that you are still learning as a leader?
- SMShishir Mehrotra
I, I think how to, how to make teams work well together is a topic that, you know... And, and interestingly, there's a group of people who view AI as a, a future state where there's gonna be we're not gonna need teams and employees anymore. I, I view it the exact opposite way. I think our teams are getting bigger faster. I think now the, the mix of I can have virtual teammates and human teammates makes every teamwork problem harder. Um, I think that's an area where, you know, I, as you know, I spend a lot of time thinking about rituals and how-
- LYLuba Yudasina
Mm
- SMShishir Mehrotra
... teams operate, and I think this-
- LYLuba Yudasina
And you're writing a book about it, right?
- SMShishir Mehrotra
I'm writing a book about it, A- A- Rituals of Great Teams. But I, and I think it's still a topic where I'm constantly learning some pattern that is different than what we're doing and hitting some roadblock. Um, that's definitely a topic area. On a personal level, I think the... I think there's, you know, every leader has their core skills, and you know, you want to amplify your core skills and continue to work on the ones which are maybe less obvious. Um, I think I'm, uh... I think that for me there's a, there's a lot about how, uh, like I said earlier, I'm, I'm the optimist in the room.
- LYLuba Yudasina
Mm-hmm.
- SMShishir Mehrotra
I think the how do you take people through that journey, maybe people that are more, um, that aren't inspired the same way. Um, so I'm constantly working on, on, um, different ways to, to, to navigate, you know, people that see, see the world through different eyes. Yeah.
- LYLuba Yudasina
It's like, sounds like finding the right language or the right tools to inspire people that maybe don't think or view the world the same way.
- SMShishir Mehrotra
Or, or hold them accountable-
- LYLuba Yudasina
Right
- SMShishir Mehrotra
... or dri- drive urgency.
- LYLuba Yudasina
Yeah.
- SMShishir Mehrotra
I mean, these are all... I mean, it's very related to teamwork, but I think it's, uh, um, I think constant area of, of growth for everybody.
- LYLuba Yudasina
And how are you learning this? What are your s- your strategies?
- SMShishir Mehrotra
I mean, for rituals, I think it's, um... I mean, for both, I'd say I just, you, you, you wanna surround yourself with, with, with different people. I mean, I think, uh, a lot of people work on their companies, and they lock themselves in their, in their office, and they never interact with others. Um, this is actually back to Dean Gilbert. It was one of Dean's lessons for me very early on. He says, "Shishir, you spend too much time in the YouTube building. You need to get out."
- LYLuba Yudasina
Mm.
- SMShishir Mehrotra
And that could be with, with customers and partners. That could be with peer companies. Um, it was, I, you know, interestingly, I used to have this, this standing breakfast, um, with, uh-
- LYLuba Yudasina
Chris Cox
- SMShishir Mehrotra
... Chris, with Chris Cox-
- LYLuba Yudasina
Yeah, yeah
- SMShishir Mehrotra
... over at Facebook. And, you know, and Facebook was, like, seen as a direct competitor, but, like, Chris and I had a great time, and we would, we would chat about things and learn from each other. Um, so I, I think it's, uh, it's just part of why I joined the Spotify board and joined the Walmart board was I, I feel like, um, you know, they're all time commitments. But I think you, if you're open to learning from others, you can learn from lots of different kinds of people.
- LYLuba Yudasina
Who are some people that you're learning from the most right now?
- SMShishir Mehrotra
Oh, man. Everybody. Uh, Daniel's high on my list. Daniel, the Spotify founder, and his, uh, his journey's been amazing. I think he's, uh, incredibly talented at kinda all stages of a business. He sees the world. You know, he can, he can look at world scale, and he can look at detail scale. Um, has a real learning mindset, very positive attitude. Um- I, I think I'm, I'm, uh, I'm lucky to have a great board. I think the, um, you know, Hemant I always learn from. He always has a different way of thinking about making things... You know, the way he did with Grammarly, the way he makes connections I think was, is really magical. Uh, Reid Hoffman, I think I spent a lot of time with Reid. He's, he's always got a unique view of, of, um, products, but really about people. Just sees people in a different way. Um-
- LYLuba Yudasina
How does he see people?
- SMShishir Mehrotra
You know, it's, I, uh... He made this observation that I, I really agree with, is that you can often see the reflection of a person in the product they create. So he created LinkedIn because he sees every relationship as having unknown, like-
- LYLuba Yudasina
Opportunity
- SMShishir Mehrotra
... unknown opportunity. And, and so he invests in them, and he, you know, is, like, connected with everybody, and knows-
- LYLuba Yudasina
Mm-hmm
- SMShishir Mehrotra
... knows a little bit about lots and lots of different things, and he finds an excuse to interact with people in lots of different ways. Um, and so he's just, he's just always open to learning from people. I mean, it's, I, I, I, I don't think, uh, there's many people that at, at his level of accomplishment will pay as much attention to an individual engineer or product person or whatever and, and hear their perspective and ideas with so much openness.
- 1:15:32 – 1:15:46
Outro
- LYLuba Yudasina
you so much for your time.
- SMShishir Mehrotra
All right. Thank you.
- LYLuba Yudasina
Hey, thank you so much for watching the show. If you're enjoying it, please share it with a friend and subscribe to the show. This is exactly what helps me grow it, and I can bring more exciting guests on. Thank you so much.
Episode duration: 1:15:46
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