The End of Manual Debugging

1. 0:00 – 0:24

   Back to YC for a second time

   1. AEAaron Epstein0:00

      [upbeat music] I am excited to welcome Sherwood from Sazabi, who has exited his first YC company and is coming back through the YC batch again for a second time. Sherwood, thanks so much for joining.

   2. SCSherwood Callaway0:15

      Yeah, really excited to participate in the upcoming YC batch. Uh, be back here for a second time. I think it's gonna be a really different experience, and to, uh, introduce Sazabi to, to the batch and to,

2. 0:24 – 1:36

   The AI tool fixing production bugs

   1. SCSherwood Callaway0:24

      and to the world, so.

   2. AEAaron Epstein0:25

      Yeah, amazing. So maybe to start off, um, tell us a little about what Sazabi does.

   3. SCSherwood Callaway0:29

      Sazabi is an AI-native observability platform. It's specifically designed for, uh, fast-moving engineering teams. Um, and one way to think about it is like, it's like a Datadog or a Sentry, but instead of being built in twenty-ten or twenty-twelve, it's built in twenty-twenty six, and it's aggressively AI native or uses a lot of AI agents. Um, and the idea basically came from this, uh, experience I've had, uh, over the course of my engineering career, where every time there's an outage in production, every time there's a bug, I would spend hours digging through dashboards and log searches and looking at flame graphs and kind of not really knowing what's going on, and eventually I might get to the root cause, maybe not. Uh, I felt like AI coding tools had gotten very powerful, and the, the part of my job that involved creating new software was, was, uh, really changing, but the part of my, uh, job that involved maintaining existing software wasn't really changing. With Sazabi, customers can basically ask questions about how their production system is doing. Uh, they can ask things like, uh, "Why is production down?" Or, "What does this error mean?" Or, "Which customers are affected?" Or, "Which commit is responsible?" Uh, and it makes it very easy to, to find and fix production

3. 1:36 – 3:43

   “Logs are all you need?”

   1. SCSherwood Callaway1:36

      issues.

   2. AEAaron Epstein1:36

      Amazing. And you, you kind of have a controversial take on this and how you're building it, that it's just built off of the log files, right? Tell us a little bit more about that.

   3. SCSherwood Callaway1:44

      Yes. So one of the things that we say at Sazabi is, "Logs are all you need." And it's actually one of three different, uh, sort of hot takes that we have. We call them our core principles, and they're a part of, uh, our manifesto, which we, we published. Logs are all you need specifically refers to this idea that we think you only need logs, like only need this specific type of telemetry, uh, to do observability well. Um, and that's controversial because in the past, for a long time, uh, people would say that you need something called the three pillars of observability. You need logs, metrics, and traces, and, uh, that's because, like, these different data types serve different types of queries, and, uh, some data types are, are large and some da- some data types are small. And so for different types of things, you, you, you end, end up using these different kinds of data. But the result is that you have three different things that you need to instrument. So for every engineering team out there, they need to implement, uh, logs, metrics, and traces for all of their services. That's a huge pain in the butt. Uh, logs relative to metrics and traces are so much easier to use. Like, every developer knows how to do a print statement, um, and every developer knows how to read a, a log stream. And so we think that, uh, logs kind of represent the Occam's razor of observability. Like, it's... Anyone can do it. Like, it's the simplest possible way of, of doing it. Um, then there's another thing which makes this true, uh, which is this AI paradigm shift. So in the past, logs were kind of the least valuable type of telemetry because they're mostly unstructured, unstructured. Um, that's, that refers to the fact that, like, the log line contains, like, natural language, and it's-- and you can't, like, have a machine read over it and derive a lot of insight. Well, obviously, AI changes what's possible there, and, uh, you can now have AI agents read all of your log lines and tell you what's going on. So that's the idea behind logs are all you need.

   4. AEAaron Epstein3:33

      Very cool. And obviously, observability is changing a lot over the last couple decades, but, um, talk about how you got your start early on, uh, setting up observability at Brex.

4. 3:43 – 7:42

   Inside observability at Brex

   1. SCSherwood Callaway3:43

      Yeah. So I started my career as a front-end engineer, but I was, like, the junior most front-end engineer at, at Crunchbase originally, and, um, because you're a junior, like, you don't get to work on any of the important stuff. So my team was complaining about CI/CD and about how long their builds and deploys would take. So I went down this rabbit hole, which is CI/CD, and figured out how to make our deploys faster, uh, and that led me to infrastructure and DevOps, uh, which turned out to be something that was, uh, really fascinating for me. I got basically obsessed with this problem of, like, how do we make production reliable, and how do we make developers more productive and allow them to, to, to ship faster and to ship higher quality code? So I was already kind of primed and interested in that space, and then I went to join Brex, where I was lucky to be, um, basically the third infrastructure engineer at Brex. Um, I think it was roughly employee seventy, and they had just stood up what, what they call their foundation team. My... The second infrastructure engineer I think had joined the same week.

   2. AEAaron Epstein4:39

      [laughs]

   3. SCSherwood Callaway4:39

      So I can't quite call myself the second, but, like-

   4. AEAaron Epstein4:41

      [laughs]

   5. SCSherwood Callaway4:42

      ... really close. Uh, and actually, he works at Sazabi today, which is great.

   6. AEAaron Epstein4:46

      Oh, very cool.

   7. SCSherwood Callaway4:47

      While I was at Brex, first we built out, uh, all of Brex's infrastructure that supported the company through hypergrowth, so all of our, uh, staging and, and production environments, the microservice framework, CI/CD system. Eventually, when we had rolled out, like, a lot of this basic infrastructure and the foundation team had grown a lot, we were in this position where we were starting to splinter the foundation team into different subteams and focus on different specializations. And we had found ourselves in a position where we had, like, fifty different microservices running in Kubernetes as a part of our production cluster, and they were all owned by different teams, and some teams would own multiple microservices, and it was getting hard to kind of know what was going on in production. And so the answer I didn't know at the time because I was too junior, but the answer is observability. Like, this is the reason that observability exists, is to help, uh, developers or engineering teams ask questions about, uh, their production systems. And so I was fortunate to be one of the team members that helped start the observability team at Brex. Uh, and then while working on, on observability at Brex, I became very observability pilled. [laughs] Basically, like, the obs-observability philosophy is that you can, you can have, uh, integration tests, you can have unit tests, you can have QA processes, you can have, like, release processes. You can do everything you want-Like static analysis before the code goes to production to try to make sure that it's right and that it's gonna, uh, behave well. But, like nothing really prepares you for production. It, it sort of reminds me of that, um, that Mike Tyson quote where he's like, you know, "Everyone's got a plan till they get punched in the face." [laughs]

   8. AEAaron Epstein6:17

      Right.

   9. SCSherwood Callaway6:18

      That's so true of, of shipping software. Uh, so once you're in a production, you just can't predict what's gonna happen. You can only prepare yourself to respond, uh, and that's what observability is.

   10. AEAaron Epstein6:29

       And how long did you spend, uh, building that out at Brex?

   11. SCSherwood Callaway6:32

       I worked on observability at Brex for about a year. Uh, in total I worked at Brex for about two and a half years.

   12. AEAaron Epstein6:37

       Mm-hmm.

   13. SCSherwood Callaway6:38

       The main things that we did while we were on that observability team was setting up auto instrumentation so all of, every microservice that gets created, uh, automatically receives a bunch of metrics and traces and logs, um, installing all the infrastructure that's responsible for capturing and forwarding that information to our observability systems, setting up tools like Datadog and configuring them. Like, I went, uh... I mean, Datadog is like hundreds of modules, but I feel like I've explored every single one and every knob and configuration option and, and tuned it appropriately for, for the team at Brex. Uh, and then now have done that at a couple different companies. Um, and other things like making sure that every service has, uh, like a dashboard that covers all of the key metrics and, um, and basic monitors.

   14. AEAaron Epstein7:22

       Yeah.

   15. SCSherwood Callaway7:22

       And driving, uh, SLO and SLI adoption, which is a little bit, um, more... That's, uh, some observability lingo that is more common in the, the enterprise and SRE space, but basically, uh, making sure that every team knows how to use observability tools and is measuring their services.

   16. AEAaron Epstein7:37

       Mm-hmm. And talk about your decision to ultimately leave Brex and start your own company.

5. 7:42 – 12:21

   Starting a healthcare startup

   1. SCSherwood Callaway7:42

      Yeah. Honestly, I feel like I'd been latent for a long time. Yeah, like I started my career as a, uh, through a web development boot camp, and, uh, that boot camp was here in San Francisco. I grew up in North Carolina, so pretty far cry from like Silicon Valley, startup tech culture. And while I was at this boot camp, everyone I knew was reading Hacker News and, uh, wanted to work at the hot YC startup. It was like Stripe and Gusto and, uh, Instacart at the time. Uh, and it was just an amazing experience for me and it, it made me really want to work in startups and specifically to do my own YC venture backed tech startup. So from the very beginning of my career, like that had been my long-term goal. While I was working at Brex in... I was living in New York with my roommate, uh, who was also an early Brex team member. He and I had relocated to New York together with Brex from San Francisco to help start this New York office, but the, the pandemic happens, and so we got stuck in New York with like a two-year lease. [laughs] And of course, like, what are you, what do two like software engineers do like when they have a lot of free time and no, nothing going on? So we started to talk about startup ideas and felt that we had a really special team and wanted to do something together and, uh, applied for YC and that was, uh, I guess the rest is history.

   2. AEAaron Epstein8:50

      Yeah.

   3. SCSherwood Callaway8:51

      Yeah.

   4. AEAaron Epstein8:51

      Um, talk a little bit about how you came up with the idea that you originally applied with.

   5. SCSherwood Callaway8:54

      My first company was called Opkit. We went through YC Summer '21, and which was one of the COVID batches. And what Opkit was, was a voice AI for a healthcare company. So we build LLM-based voice agents to automate calls to insurance companies for things like, uh, e- eligibility, which is basically when the, the provider, the, tries to determine whether you have coverage or not for your, your procedure, and for, uh, uh, prior authorization, which is another hoop that insurance companies make you jump through to get certain procedures.

   6. AEAaron Epstein9:24

      Mm-hmm.

   7. SCSherwood Callaway9:25

      Uh, and also, uh, to do, uh, claim, to check on the status of, of claims that have been submitted. Um, it's a pretty esoteric field. It was a very be- big field, but at a far cry from anything I'd done previous.

   8. AEAaron Epstein9:36

      Yeah. Why did you decide to work on that?

   9. SCSherwood Callaway9:38

      Yeah. It's, I was... Well, I guess, to start with, my, my dad was a doctor growing up.

   10. AEAaron Epstein9:43

       Mm.

   11. SCSherwood Callaway9:43

       Um, so I had a little bit of a lens of like, you know, if, if I know, if what I know is like just software engineering and tech startups and, you know, I need to have an idea that's like out in the real world, right? Like, that, that impacts real businesses, not like just tech businesses. So the only field that I really knew anything about outside of, um, uh, technology was, was healthcare, and I felt like I had access to my dad, who's a subject matter expert, and to his practice and his, uh, his colleagues, and I could go interview the, the staff and the, the administrators there. Um, so it felt like an opening, and it meanwhile, like I was coming from a lens of having worked at Brex and having been very interested in fintech during fintech's like real rise from like during the second half of the 2010s, and, uh, was thinking about like what's next for fintech, you know. It's seems like we've done a lot of cr- like consumer fintech and now we have like the Brexs of the world, the Brexs and the Mercurys. Um, maybe verticalized fintech would be what's next. And so I thought, why not? Like, healthcare seems like a big vertical. Like there's a lot of money moving there. Um, a- in retrospect, I think, uh, Opkit was kind of like an MBA case study approach to, to picking a company or picking an idea. It wasn't based on personal experience or insight or, uh, like, or passion, candidly. It was based on this, um, this real desire to start something and, uh, and, you know, grasping basically for, for whatever I think I, wherever there was an opportunity.

   12. AEAaron Epstein11:12

       Yeah. Did you ever consider moving outside of healthcare or for, you know, the la- You spent years working on Opkit.

   13. SCSherwood Callaway11:19

       Yeah. Yeah.

   14. AEAaron Epstein11:20

       Wa- was it always like, this is a healthcare company and we must stay within healthcare?

   15. SCSherwood Callaway11:24

       Yeah. We, you know, I regret not evaluating that like fu- fundamental condition more carefully. Um, I mean, actually I don't have a ton of regrets because I am here where I am today, and like, uh, those, there were a lot of hard lessons learned from Opkit, but now Sazabi gets to benefit from all of them. But we went in like with a healthcare idea and I, you know, my c- my co-founder Justin and I love working together and we felt like we were learning a lot and making some progress. Slow, slow and steady progress, um, and peeling back layers of the healthcare ecosystem and learning about new problems within the space. So we, we enjoyed it, but I don't think that it was the right thing for us to be working on. And, um, one thing that I wish we had, uh, thought, thought more about is like whether this is really playing to our strengths.

   16. AEAaron Epstein12:08

       Mm-hmm.

   17. SCSherwood Callaway12:10

       And I think that's like a great piece of advice for, for YC founders and founders in general is like look for your personal expertise or, um, or b- or build f-based something, something based on your prior experience.

6. 12:21 – 17:02

   When the first startup unraveled

   1. SCSherwood Callaway12:21

      You probably have more prior experience than, um, than you think, and there are probably more openings there than you realize.

   2. AEAaron Epstein12:27

      Yeah.

   3. SCSherwood Callaway12:28

      You don't need to build a business in some other field just because it feels like whatever you're, you've been doing is, is not real.

   4. AEAaron Epstein12:34

      Yeah.

   5. SCSherwood Callaway12:35

      Um-

   6. AEAaron Epstein12:35

      Yeah, we tend to see that a lot, people that have a lot of experience in an area. For you it was, you know, observability and even in fintech, you probably had a lot of fintech experience, much more than, than other, uh, people would.

   7. SCSherwood Callaway12:47

      Yeah.

   8. AEAaron Epstein12:47

      And then explicitly saying, "I don't wanna do that because I, either I know too much about it so I know, you know, all the problems or what's gonna be difficult about it, um, or I'm kind of burned out on it-

   9. SCSherwood Callaway12:58

      Yeah

   10. AEAaron Epstein12:58

       ... and so I'm gonna go and do something that I've never done before and I don't have the, the depth of experience or insights on." Was there a moment when you were building Opkit, maybe in hindsight looking back, where you're like, "I should have known at this moment that this was not the right thing for us"?

   11. SCSherwood Callaway13:14

       I think what's funny, it was like we were definitely not the right team to start a healthcare fintech company or a healthcare AI company when we started, but progressively we became that team.

   12. AEAaron Epstein13:24

       Mm-hmm.

   13. SCSherwood Callaway13:24

       So ironically, like if I had, if I... if Sazabi were a, a different kind of company it could be a healthcare or a health tech company because we have now four years of hard-earned experience in that space.

   14. AEAaron Epstein13:34

       Right.

   15. SCSherwood Callaway13:34

       And at some point it was like, oh, we've got one year of experience in this space, and we're like, "No, more than anyone we talk to." Um, and I guess this is the definition of the sunk cost fallacy, but, uh, there were, there were times when we, especially during YC, which was at the very beginning of our company, uh, which really kind of like kicked us out of the, out of the nest so- to some extent, um, where we evaluated it, but we... I don't think we went deep enough about that or really reckoned with like what it would look like for us to spend the next 10 years of our life working on a healthcare or health tech company. Um, yeah, we should have thought harder about that.

   16. AEAaron Epstein14:07

       Yeah.

   17. SCSherwood Callaway14:08

       [laughs]

   18. AEAaron Epstein14:08

       Well, it's like the curse of the second time founder a lot of times is-

   19. SCSherwood Callaway14:11

       [clears throat]

   20. AEAaron Epstein14:11

       ... coming up with the idea to work on because you know too much, and-

   21. SCSherwood Callaway14:15

       Yeah

   22. AEAaron Epstein14:15

       ... one of... I mean, you're describing naivete of jumping into this space that you knew nothing about-

   23. SCSherwood Callaway14:20

       Yeah

   24. AEAaron Epstein14:20

       ... and trying to learn as quickly as you can, but sometimes that's what's needed too just to be able to-

   25. SCSherwood Callaway14:25

       Yeah. I, I think that's true. I mean, I think that if you're, especially if you're like a really young person and you're ready, you wanna get started, you... like you can be an expert at anything, but you have to be prepared to put a couple of years of experience in, um, to, to learn the ropes, to ramp up, to build a network, um-

   26. AEAaron Epstein14:40

       Yeah

   27. SCSherwood Callaway14:40

       ... to gain trust with, with people in the space.

   28. AEAaron Epstein14:42

       Yeah.

   29. SCSherwood Callaway14:43

       'Cause, um, th- those things are required I think. They're preconditions for success.

   30. AEAaron Epstein14:47

       Yeah.
7. 17:02 – 22:51

   The insight behind Sazabi

   1. AEAaron Epstein17:02

      Yeah.

   2. SCSherwood Callaway17:02

      And we did that pivot in our last, or in our second year at Opkit. Um, and so then our... we had about a year worth of runway left to build and commercialize that solution, basically retool the company, reframe it, and then, uh, and go out and try to raise the seed extension to see if we can kind of keep things going. And got to the point where we had about six more months left of runway. We had prepared all of our materials. We had launched the products. Uh, went out to fundraise. Some of our early conversations were, were not that exciting. Um, kind of didn't seem like investors were super, super interested, and that led us to reconsider whether this was the right thing for us to be doing.

   3. AEAaron Epstein17:39

      Mm-hmm.

   4. SCSherwood Callaway17:39

      And so, um, our decision was that it was not, and there's still plenty of time for us to go do something better.

   5. AEAaron Epstein17:44

      Mm-hmm.

   6. SCSherwood Callaway17:45

      So we then started to seek out a, a- acquirers, and talked to a lot of growth stage healthcare companies and growth stage fintech companies, and that, to be honest, that felt like more of the same. You know, we'd be, we'd be in a larger organization doing some of the, working on some of the same problems we've already been working on.

   7. AEAaron Epstein18:01

      Mm-hmm.

   8. SCSherwood Callaway18:01

      Uh, and then we talked to one AI sales tech company called 11X, which is based here in San Francisco, um, that was growing super fast. They were building a voice agent. We, we knew their CTO from, from Brex.

   9. AEAaron Epstein18:14

      Mm-hmm.

   10. SCSherwood Callaway18:14

       And it seemed like, uh, a much more exciting-Place for us to be. We wanted to get closer to, to AI, and so we decided to join Eleven-X.

   11. AEAaron Epstein18:22

       Very cool. And yeah, talk about the decision to leave that and then start Sazabi again and

   12. SCSherwood Callaway18:27

       Yeah, I mean Eleven-X was am- amazing and, and, uh, I'm really proud of the product we built there, and the team we... Our, our team came in and, and did a lot of great engineering work there. But, uh, first thing we did was rebuild their AI SDR product, their sales rep, and that was probably like a three to four-month-long project of, you know, building it from scratch, uh, cutting over from the old platform to the new platform and, and scaling it and kind of getting it to steady state. And in month like five, where most of that work had been done, we're now in sort of maintenance mode, and that's like, okay, well, I've now set up Datadog again.

   13. AEAaron Epstein19:01

       Mm-hmm.

   14. SCSherwood Callaway19:01

       I've set up all of the observability tools and CI/CD tools that I always set up, and because I'm tech lead for this project, anytime something goes wrong, like I get a Slack message, or someone, like a, a go-to-market person comes and like taps on my shoulder. Um, so now I'm like the on-call guy.

   15. AEAaron Epstein19:16

       Mm-hmm.

   16. SCSherwood Callaway19:16

       And I found myself... We had, we're building a futuristic AI product using futuristic AI coding tools, and then when I would go to debug it, and it was the same painful manual experience that I've had for my entire career. Uh, and so it was just, it, it, it was painfully clear to me that, uh, we were going to do to, uh, observability what was already being done to, uh, like code generation or, or, or the, the act of creating new code.

   17. AEAaron Epstein19:43

       Mm-hmm.

   18. SCSherwood Callaway19:44

       Uh, and I also realized, wait a second, like this is like the perfect company for me, right?

   19. AEAaron Epstein19:49

       Mm.

   20. SCSherwood Callaway19:49

       Like it's, it, it's completely aligned with my interests, my experience, my combination of experience and, and now AI and, uh, and infrastructure and dev tools and observability and, you know, I'm a s- I'm, I, I've already been a founder, so I kind of, it's not, it wouldn't be a scary, new thing.

   21. AEAaron Epstein20:07

       Yeah.

   22. SCSherwood Callaway20:07

       Like I know how to fundraise, I know how to build a team, uh, I know how to do a big launch. I know how to do press. Um, so all of the, I, I felt like I had all of the right i-ingredients to do this company and that this was like the company I was born to, to build.

   23. AEAaron Epstein20:23

       Yeah.

   24. SCSherwood Callaway20:24

       So...

   25. AEAaron Epstein20:24

       Talk about anything that you specifically want to do differently with this company based on-

   26. SCSherwood Callaway20:28

       Yeah

   27. AEAaron Epstein20:28

       ... lessons that you learned from building Opkit.

   28. SCSherwood Callaway20:30

       Yeah, I mean, the, the big one was like, build something I know.

   29. AEAaron Epstein20:33

       Mm-hmm.

   30. SCSherwood Callaway20:33

       Uh, leverage my personal experience, pl- play to my strengths, call it Sazabi, because it should be, uh, it should be a representation of who I am. Um, another one is that I thought it should be fun, and I think as fun as Opkit was, like I, I loved working with my co-founder and my best friends. I loved going through YC. Uh, healthcare was like intellectually rewarding and, and interesting and, um, there were a lot of new experiences, which were, which was, which was great. I can't say that it was like fun.
8. 22:51 – 27:00

   Returning to YC

   1. AEAaron Epstein22:51

      for a second time.

   2. SCSherwood Callaway22:51

      Yeah. This one is interesting. I feel like there's like a lot of reasons not to, right? It's like, uh, I've already done YC. I'm already a part of the network. You know, I've already got access to Book- Bookface. Um, you know, it's on my resume, which I feel like that's what a lot of people want.

   3. AEAaron Epstein23:06

      Mm-hmm.

   4. SCSherwood Callaway23:07

      So it's a little counterintuitive. Um, I guess from a business perspective, the first thing that comes to mind is that YC is an accelerator and, uh, we need to accelerate, like Sazabi needs to accelerate. Uh, our opportunity is here today, like will not be here forever. There are other companies that will try to do it.

   5. AEAaron Epstein23:24

      Mm-hmm.

   6. SCSherwood Callaway23:25

      And, uh, I don't want to waste any time. Like it feels like very ephemeral to me. So I, I want my team to move fast. I think YC will help us move faster. Um, another thing is kind of, um, culturally, I w- I, I want like to establish a culture at Sazabi that is kind of based on some of the, or is imbued with some of the YC values. Like YC will create, like it creates a deadline for us very early. It has many, there are many smaller deadlines along the way. So we just have to get used to this, uh, this cadence of shipping quickly. And, um, YC also pushes you to get to market super fast, which I don't... We have a team of engineers, right? We're like eight engineers or something. So yeah, it's, it would be very easy for us to just build forever-

   7. AEAaron Epstein24:04

      Mm-hmm

   8. SCSherwood Callaway24:05

      ... and not commercialize. So I want that. Um, and I, I guess on a, the, the last note related to, um, from, from a business perspective is g- distribution and go to market. Um, and this is like a little more tactical, but, you know, every YC company is a software company. Every software company has an observability solution.Sazabi should be that solution. Um, I'll be following in a tradition of great YC companies like Brex and Deel and Rippling that have sold into, uh, their batchmates-

   9. AEAaron Epstein24:36

      Mm-hmm

   10. SCSherwood Callaway24:37

       ... uh, really successfully. Uh, and I, I think that Sazabi can do the same thing, so I wanna use that as an opportunity.

   11. AEAaron Epstein24:42

       Yeah.

   12. SCSherwood Callaway24:42

       Um, then on a personal level, my first YC experience was, uh, was remote. Uh, we were one of the COVID batches, so it's a really different experience. I mean, I'm here in this space today that I've actually... I, I've never been in this building before, uh, which I think is like e- um, points to the fact that I have not had, like, the full experience and, uh, it's been a dream for a long time. So I want, I wanna, uh, I wanna stand on the stage at Demo Day and, and actually have that experience and, and make real connections with my batchmates, um, that happen here in person.

   13. AEAaron Epstein25:15

       What's something you wish you knew at the beginning of this journey? You've, you've been through the arc of starting one and-

   14. SCSherwood Callaway25:21

       Yes, which beginning are we talking?

   15. AEAaron Epstein25:22

       ... exiting and, exiting it and starting a new one-

   16. SCSherwood Callaway25:25

       Yeah

   17. AEAaron Epstein25:25

       ... and, um, maybe if there was something that, uh, you could go back and tell yourself at the beginning of-

   18. SCSherwood Callaway25:30

       Hmm

   19. AEAaron Epstein25:30

       ... uh, the Opkit journey, your first time going around during YC. What, what is the advice you would give yourself?

   20. SCSherwood Callaway25:36

       I wouldn't wanna give any advice that would actually change the outcome, 'cause I think I'm building the, the perfect company today.

   21. AEAaron Epstein25:40

       Mm-hmm.

   22. SCSherwood Callaway25:41

       Um, and then I think all of the years of, like, eating glass with Opkit, like, that's, like, my Glenn Gle- Glengarry Glen Ross period, right? Where I'm just, like, knocking on providers' doors, and they, like, don't wanna take my meeting. And, um, we built a lot of grit and learned a lot about, like, how to build a startup under tough circumstances. Uh, so I'm really grateful for those lessons and would not give them away. Something that I might tell myself, or maybe just remind myself, is that startups are... You know, a lot of people perceive startups to be short and fast, but actually we are in a long-term game. It's like a long horizon game.

   23. AEAaron Epstein26:20

       Mm-hmm.

   24. SCSherwood Callaway26:20

       And the lessons I learned from Opkit, the relationships I built, uh, with investors, with customers, with other engineers, like, I still keep up with my batchmates. Um, the... You know, I, I, I've... Many of my batchmates are starting other companies that I could sell into or, um, that, like, I could potentially recruit them. Like, these are relationships that w- we, you build over a long period of time, and, uh, they compound. And so it's, it's good to remember, to remember that, be mindful of it, uh, have integrity, be good to everyone you work with, 'cause you never know. Like, five years from now you might be asking them for money. Um, so yeah, I, I would... I think that's a good, uh, good tip

9. 27:00 – 29:42

   Lessons for founders + hiring

   1. SCSherwood Callaway27:00

      probably.

   2. AEAaron Epstein27:00

      For anybody that's watching, talk about, um, hiring-

   3. SCSherwood Callaway27:04

      Yeah

   4. AEAaron Epstein27:04

      ... and the ideal engineers-

   5. SCSherwood Callaway27:07

      Yes

   6. AEAaron Epstein27:07

      ... to come and work at Sazabi.

   7. SCSherwood Callaway27:08

      We are definitely hiring. Uh, we're hiring a lot of different roles. I would say that the ideal candidates are, uh, they're high agency, they learn quickly, they, they love tools. That doesn't need to be dev tools specifically, but just tools. Like, they kind of geek out on the, the saw, so to speak.

   8. AEAaron Epstein27:27

      Mm-hmm.

   9. SCSherwood Callaway27:27

      Like, the thing that makes you, helps you do the thing. Former founders are great. Uh, people... I mean, former founders just, like, have to figure things out.

   10. AEAaron Epstein27:34

       Mm-hmm.

   11. SCSherwood Callaway27:34

       You know, it's... And, and, uh, they know what it's like to just do hard work, to, um, to put in long hours or to do things that are un- unsexy. Uh, they're also very flexible, and I think right now with AI, we never, we don't really know what our jobs are gonna look like or what the, what the org structure and the different departments are gonna look like two years from now. So we'll, we need people who are flexible and self-starters. Uh, on a more practical level, like, we're looking to basically hire software engineers in a lot of different roles. So, um, data and databases and infrastructure are hugely important to Sazabi. Like, we build our own log ingestion and storage system. It's one of the things that sets us apart from a lot of other observability tools, and so, uh, we need to have best-in-class infrastructure and, uh, expertise at, at the database level or the storage level. Um, we need full stack product engineers, of course. Uh, and we also need, like, front end and, uh, design engineers. So people who... You know, I like to say that we're building the Linear of observability. Like, it's gonna look and feel amazing, um, because, you know, if you look at Datadog, it, it does not feel that way.

   12. AEAaron Epstein28:37

       [laughs]

   13. SCSherwood Callaway28:37

       Um, so I wanna, I want to hire engineers who have, who, like, appreciate aesthetics and design and-

   14. AEAaron Epstein28:43

       Mm-hmm

   15. SCSherwood Callaway28:43

       ... um, and attention to detail. And so that, that's where the front end, uh, and design comes into play.

   16. AEAaron Epstein28:48

       Amazing.

   17. SCSherwood Callaway28:49

       Yeah.

   18. AEAaron Epstein28:50

       Well, Sherwood, thank you so much for joining. Um, super excited to work with you on Sazabi as well. Uh, I think you are gonna build, uh, a massive generational company because you're building something that you know a lot about and that you're passionate about and that you have deep insights in, and I'm so glad you came back home-

   19. SCSherwood Callaway29:07

       [laughs] Yeah

   20. AEAaron Epstein29:08

       ... to the thing-

   21. SCSherwood Callaway29:09

       Yeah, thanks for finding me [laughs]

   22. AEAaron Epstein29:10

       ... yeah, that you know, you know, you know so well, and really is the space and the idea and the business that you are the exact right person to be building.

   23. SCSherwood Callaway29:18

       Yeah. I hope that, um, I hope that other founders can kind of learn from my, my story and, and find whatever their, like... Uh, I've heard it referred to as a tombstone company.

   24. AEAaron Epstein29:26

       Mm-hmm.

   25. SCSherwood Callaway29:26

       So I want other developer, or other founders to find their tombstone company-

   26. AEAaron Epstein29:29

       Yeah

   27. SCSherwood Callaway29:30

       ... um, and to come do it here at YC.

   28. AEAaron Epstein29:31

       Yeah. Amazing.

   29. SCSherwood Callaway29:32

       So.

   30. AEAaron Epstein29:32

       Thanks for joining.

Episode duration: 29:42