The Exchanges

Q What'd you, what'd you learn from the founders there? What'd you learn from the team?

A Um, that, you know, I was never thinking big enough. One of my favorite stories was, I remember I was helping my friend Brian Rakowski, who was, You know, this guy had first job out of school, out of Stanford, and he was given, you know, Gmail. That was his project, was to help Gmail out. And I remember sitting on the, the product review with him, because I was helping him out at that point. And I remember the Gmail team saying, oh, maybe we should like, um, maybe we should give people 10 times what, uh, they're being given today on Hotmail. Because remember, back in those days, Hotmail was the dominant email service, and so was Yahoo Mail. And they had 25 megabytes of storage. And you would sit there and go like, wow, it's, you know, not a lot. But, you know, back then it was, State of the art that you would get 25 miles, uh, 25 megabytes of cloud storage. And I remember the Gmail team sort of, you know, pitching an early version of this to, to Larry going like, you know, we think we can do 10 times and do a 250 megabytes, which sounded like, you know, a lot back then, right? You know, you're giving, you're getting a quarter of a gig. And Larry kind of sat there and was like, why are you wasting your time on like a 10 X improvement? That doesn't sound very much. And everybody's like, well, that's a lot. You're getting 10 X. He's like, let me start something, you know, sort of …

AI assessment note: “that, you know, I was never thinking big enough.”

Q You've ended up investing in a very large number of successful companies. Tell us, tell us a couple of those stories. What were some of your early wins that you had?

A Boy, you know, I'll probably tell you my favorite, which is this fantastic company with this very humble founder in Australia, Melanie, who started Canva. And Canva is today is YouTube for design. They're the reinvention of design, you know, every school Student, uh, is using it for their homework, and it's one of these things where I've never seen such incredible traction, incredible growth, and such a commitment to reinventing how people build beautiful things and make design simple, and so, you know, I think it's one of the most valuable, uh, companies run by a woman entrepreneur, uh, that's private today, and then, you know, I think it's one of the fastest growing private companies, uh, on the planet. They're based out of Sydney, but it's one of these companies where, you know, we were privileged enough to find Melanie and Cliff, her co-founder, uh, and, uh, lead their Series A, and it's been this amazing journey to sort of watch them Uh, you know, build, you know, the next generation tools for building, you know, beautiful things. Uh, whether it's business cards, websites, presentations, it's the, it's a, it's a tool that basically democratizes design for everybody.

AI assessment note: “I'll probably tell you my favorite, which is this fantastic company... Canva”

Q So you, you ended up, I know, working with the leaders of Google. How, how did that happen?

A Um, you know, it was just a small enough company then. It was just really fantastic to be able to be at a place where it seemed like a family. Everybody would eat dinner together or lunch together in the same sort of like small cafeteria. Uh, you know, you, you'd show up there and you'd be like tasked on the seven projects at once because there were, you know, as Larry sort of said, there was just way too much to do and too few people. And so the opportunity was just endless. You know, my first job there was to, to help sort of product manage, uh, you know, what was called the Google client team, uh, which became Google Chrome. Like it was the team that, you know, helped, uh, Build Google Chrome. And, you know, back then it was Google toolbar, and it was Google, uh, it was this, uh, this fast search for Google that would predict, uh, you know, what you would type into your keyboard and sort of preload the searches on your client. Um, and it was all these pieces that eventually became, you know, Google Chrome, but it was one of these things where he's like, you're in charge of this now, because it's like, you know, it's somebody else's side project, and we want you to spend some time on it. And by the way, like, we'd like you to spend some time writing the ad system. And I was like, huh, that's a lot of random things.

AI assessment note: “it was just a small enough company then... way too much to do and too few people”

Q Were a lot of people more pessimistic at that time because the dot-com boom obviously crashing? Was it the HP kind of lost its interest in this or just that they had to for monetary reasons?

A You know, I, I, I was, I was, It was way above my pay grade at that point. And, you know, being fresh out of MIT and sort of like going, oh, I got this great job at HP and going like, oh, this is not the place, you know, I think people are happy. And, uh, you know, but you have to look at the context of that time when, you know, I, I went through six roommates in less than, in less than three months because I, uh, I just kept watching them having to pack up everything in a U-Haul and move back to Ohio or wherever they were from to, to move in with their family, which was just really sad at that point because, you know, all the stars were imploding and I just would have to keep posting You know, I was in a two bedroom apartment in Palo Alto then. I kept having to post messages on Craigslist going like, hey, you know, I was, uh, if you're, if you're looking for a cheap room, I got one for you. Uh, and, uh, you know, I think a bunch of people like Alan Eustis and whatnot had, uh, who was the head of a compact lab had just migrated to Google. And, you know, I was like, come join this place. And it was just one of these little interesting places where I was like, I could never see myself in a search company, but.

AI assessment note: “all the stars were imploding and I just would have to keep posting”

Q Was there a sense when you were building it, like, this is going to be the number one email provider in the world, and there's a really good chance it will be, or it might be, or like, what was the energy around that?

A I mean, it was just, everybody just wanted to go build the best thing that they could build for themselves, right? And then, you know, by definition, if they built it great for themselves, it would be, it would be one of the things that would be good for the world. So I think, you know, we first and foremost wanted to build something that we would be proud of sort of using ourselves, and I think that's one of those things at Google where, where you would look at this and go, well, You know, what could I build that would be something mind-blowing for me, and if I could do that, I could do that for the rest of the world.

AI assessment note: “everybody just wanted to go build the best thing that they could build for themselves”