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.
00:15:29 · Aditya Agarwal, Waseem Daher
[00:15:29] S1: Yeah, one of the things that I find hardinteresting about listening to people I admire is that they all often offer contradictory advice, particularly around startups. Everybody seems to have some set of things that they believe have led to essentially a place that you admire. And so I think a lot of the actual journey in starting a company is one of self discovery, right, which is then being able to map like, who am I and what works best for me? Right? And then being able to find the people that you also remind, like, this person actually seems to be cut from similar cloth. Because otherwise, it's very easy to get inundated because... And if you really do them... Like, if you kinda go out and canvas, there's a lot of contradictory advice about, like, early stage ideation, early stage philosophies. So I'm often, like, more kinda seeing, like, what resonates with me, what actually maps to my world beliefs. So it sounds like you're a man of action. [00:16:28] S0: I like that phrasing. I'll take that. [00:16:30] S1: Okay, all [00:16:30] S0: yes. But I agree with you. I mean, there's some tweet, and I don't know who sent it, was like, the entrepreneur's advice is like, these are the numbers that helped me win the lottery. It's like, yeah, okay, cool. It's not like... That's not that actionable for me. I might [00:16:45] S1: steal that one.
00:16:45 · Aditya Agarwal, Waseem Daher
[00:16:45] S1: steal that one. [00:16:46] S0: That and like, this advice is kinda worth what you're paying for it, which is everyone's advice is sort of an imperfect distillation of what they thought worked for them, which it may or may not actually be like what it really did, and I have been surprised, even just in reviewing my own notes, how much revisionist history I have about the world. [00:17:08] S1: Yeah. I mean, I think that it's actually really hard to go back. So I famously, my team is, they don't love me for this, but I hate post mortems because you're trying to go and relitigate a decision that was done in the past. But my firm belief is that it's actually very hard to go and re litigate it using the exact context window that you had at that point in time. So, we can try to re litigate it using new decisions. But trying to go and literally the question is, how would I have done it differently? I'm like, that question doesn't make any sense to me. Right. Because I'm no longer that person. So, we can choose to how would this decision look different today. But that's a very different question than relitigating something that happened in the past. But with that framing, I'm curious, what are some of these things that you have learned about yourself as an entrepreneur and your ability to navigate the mine is one that you might be different today or might be different when you started Pilot relative to when you started, let's say, Ksplice?
00:18:10 · Waseem Daher, Aditya Agarwal
[00:18:10] S0: So what evolved in our thinking across these three startups? I think one is we were much, much more attuned to market size, which is in the first company, again, it was just like, oh, this is cool. Let's do it. In the second company, it was like, this is a problem we have, and this seems like the world needs this, and it seems big enough. Let's do it. And then with Pilot, I think it was much more like, okay, well, actually, the TAM here is like every small business in The United States, and they all need accounting, and they need tax prep, and they pay a lot for it, and, you know, you multiply the numbers, and, like, the numbers are very big. The TAM is, like, functionally infinity. Like, we spent a lot more time kind of pressure testing against that as opposed to literally for Case Plus, it was like, this seems cool. Like, let's go do it. I think that was correct if your objective is to build a venture scale business, which was our objective. Like, in some ways And you have. And we have. And in some ways, like... One of the, like, maybe not as noble motivations for doing Pilot was a little bit like, you look around, you see, like, these other unicorn or public company CEOs, and you're like, yeah. They're smart, but, like, they're not they're not smarter than we are. [00:19:23] S1: Like, you know, I'm like, we
00:19:23 · Aditya Agarwal, Waseem Daher
[00:19:23] S1: Like, you know, I'm like, we [00:19:24] S0: can do this. Like, I mean, if they're doing it, like, we can probably do it. So there's a certain amount of, like, we chip on our shoulder about that too. And it's like, obviously, that's an input too of, like, okay. Fine. What kind of thing do you wanna build? Because the other path... And this is now, like, more in vogue, and I think, you know, in 2017 when we started Pilot, it was not. It was like, well, you build this thing that's super small, and you don't take a ton of capital, and you have huge ownership. And actually, that probably maximizes dollars in your pocket, but it's a very different shaped thing. [00:19:52] S1: It's interesting. Yeah. So by the third company, you were thinking a lot about markets from day one. Yes. And less about, is this fundamentally something cool? Is this something that is flashy? It's like, hey, I just don't want to take market risk. [00:20:08] S0: Yeah, I think we believed that basically that the technical risks were extremely surmountable by our team because it was just a very, very strong technical team, on almost any domain. It was like, fine, so what are the things that we really need to derisk? What is the market opportunity, and what is the market risk? [00:20:26] S1: What do you think is the biggest market opportunity today?