00:08:59 · Aditya Agarwal, Waseem Daher
[00:08:59] S1: So did you I'm always curious to dig into the details. This top down ideation? Is this bottoms up in the sense that top down you identify a market, then you go and essentially build out the business case for it and then go out and essentially build it? Or was it a little bit more like, ah, this could be cool. I'm going to go start building it and then essentially let the overall narrative come out of the act of building? Or were they somewhere in between? [00:09:25] S0: For Zulip specifically, it was, again, about a specific problem to be solved. So it was not a top down analysis. And the the origins of Zulip specifically is there was a group chat tool at MIT called Zephyr, which was this, like, nineteen eighties messaging tool that was kind of contemporaneous with IRC and, like, used in a very, very niche way at MIT. And it was actually what we used internally at Ksplice. And so one of the pitches, kind of as we thought about it, was like, can we bring this idea of Zephyr to the masses? Can we actually successfully have it be a robust tool that people use at work? [00:09:58] S1: I see. So Zephyr then got acquired into Dropbox. That's where I met Waseem, and then Waseem spent three or four years at Dropbox. [00:10:04] S0: I was at Dropbox for two years. [00:10:06] S1: And one day? Two year... Yeah. [00:10:07] S0: I think probably like two years and then a month or two. [00:10:09] S1: Okay. Alright. [00:10:09] S0: And then I took six months off, and then we What started [00:10:13] S1: did you learn about startups from Dropbox?
00:10:13 · Aditya Agarwal, Waseem Daher
[00:10:13] S1: did you learn about startups from Dropbox? [00:10:15] S0: A lot, actually, which is Dropbox was either tied with or a close second to it, probably tied with MIT on just sheer talent density. So we had done our first two companies in Boston, and I think we had a little bit of a chip on our shoulder about that, which is we're like, oh, you can build a good tech company in Boston like it is possible. [00:10:36] S1: I didn't know that KSplice was in Boston.
00:10:38 · Waseem Daher
[00:10:38] S0: Oh, yeah. Because we were just... Was right out of MIT. And so we, like, just... You know, we were down the street in Central Square. We, like, we just feel like... We stayed in our hood. You know? And then, actually, Drew came out, like, a bunch because he was back for MIT stuff. He was like, you guys have to move to California. This is kinda where it's all happening. And so I think we were, like, a bit... You know, there was inertia. It's like, well, you know, my friends are here, and it's, like, it's annoying to move. I think one of things we saw at Dropbox is like, oh, wow. The talent density here is just, like, enormous. So I think that was piece one. And then piece two is, like, there are disciplines that I kind of knew nothing about, that I had sort of, like, been a little bit self taught on by virtue of doing our startups. Because remember, before this, I, like, had not had a real job. Like, I had done summer internships. Like, I was an intern at AOL. Was an intern at Amazon, and I was an intern at Google. But, like, I had not really worked at a real company before. And so at Dropbox, I think it was, like, very instructive to see, like, oh, this is, like, world class design talent or this is what really good sales looks like or this is what the marketing team even does. Know, it's stuff like that. I think it really broadened our horizons and then also gave us a little bit of a preview of, like, okay, this is what a company looks like at this size and stage and scale, and these are the things that are working, and maybe these are the things that are not working as well. And I think that was actually very helpful in thinking about the roadmap for Pilot.
00:12:00 · Aditya Agarwal, Waseem Daher
[00:12:00] S1: You do Zulip. You get acquired by Dropbox. You stay there for two years. But then this time around, instead of kind of jumping into your next thing, you decide to come to SPC very early. Right? And this is when the first SPC office, I think, at 112 South Park, maybe 27th? [00:12:18] S0: South Park. Yeah. That's [00:12:19] S1: right. When Ruchi was kind of, like, running it. So what prompted the slight change in your ideation kind of, like, maze? Like, why join SPC in the early days?
00:12:29 · Waseem Daher
[00:12:29] S0: Sure. So first of all, between... So we started Zulip immediately after we left Oracle. Yep. And here, after I left Dropbox, I took some time off. I took about six months off and just, like, spent time with my friends and family, and I went and spent some time with my parents and, like, worked out a lot and just, like, sort of recharged with the understanding that was gonna come back in six months and then actually, like, you know, start to tackle this in earnest with Jeff and Jessica. And at the time, SPC was really... It, like, was not as structured as it is today. It was really kind of like Friends of Ruchi hang out in this in this room Mhmm. Which actually, like, it was still quite unstructured. Yeah. And so I think it led to a little bit of, okay. We know we wanna do something. This is sort of a way to provide a little bit of a frame around that. And I remember actually that time being very unpleasant, not because of SPC, but because actually, like, the thinking about what you're gonna do, it's so unstructured. You can't really do it for eight hours a day. You can't just like sit there and think like it's actually... It's not really how it works. And, you know, your internal critic is very strong. There are a million reasons why you come up with the idea, and there are a million reasons why it's not gonna work, and you sort of like are forced to contend with those in the process of kind of thinking this through, and I found that very, very unsatisfying. The things I liked more was like, okay, we have a thesis. Now let's go test it. And we'd go and we'd try to find some potential customers. We'd talk to them and say, what are you doing about the x y z? And this is a problem you'd have. Like, that I enjoyed because it was like, okay. You know what you need to do. There's kind of like, you can apply energy towards it and advance, you know, the the thing you're exploring. Whereas just like sitting around, like, brainstorming about, like, well, maybe we should, like, build a credit card, or maybe we should start a city, or, you know, maybe we should... It's like... It's a lot more unstructured. So I I guess
00:14:22 · Aditya Agarwal, Waseem Daher
[00:14:22] S1: is that more an observation about your lived experience? Or is that more almost your methodology for how you think about navigating the idea, Mace, which is that you must have some kind of like your vector must be moving in some direction. [00:14:38] S0: I think you're happiest if you have a series of hypotheses that you're quickly testing and deciding to further explore or to cut off. Okay. But I also let you know. I don't know. Tim Abbott, who was also at SPC and who was at Dropbox and who was both Ksplice and Zulip with us, he's like a math genius in addition to being very talented at many other things. And I would sometimes just like find him sitting, like in the computer club at MIT, he would just be like sitting there. I'd be like, what are you doing? And he's like, I'm like thinking about math. He was like he was like just like working on a proof or something, but just like there in his head, if like the gears were just turning. It's like that's not how I sort of ever have been. It was I like I prefer the much more active, like, okay. I wanna go and like test it in the world and kinda see, you know, how it holds up, how how my assumptions change in the presence of new data.