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.
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?