Why Nobody Needs Metrics or Traces Anymore | Sherwood Callaway (Sazabi)

13:22Lindsay Pettingill:And is that how you met Rex, Rex Salisbury, who also went to Davidson? Not originally how I met him.

13:28Sherwood Callaway:So Rex was class of 2010 at Davidson. That was class of 2016, so we did not overlap. Rex is now one of the only and most successful Davidson alumni in tech in San Francisco. I stayed on his sofa for like a month when I first moved out here. He did Dev Bootcamp too. I think he did it a couple of months after I did. But because he was, I think at that point he was a couple of years into his career, he was transitioning from an actual banking role to an engineering role at a fintech company, which is like what he's known for today. Yeah, I mean, he's an investor.

14:04Lindsay Pettingill:We've done a number of deals with him.

14:05Sherwood Callaway:Yeah, he rocks. He said he's obviously invested in Sazabi. Yeah. And he's said repeatedly that DevTools thing. DevTools are not his thing. But if it's working, he doesn't mind.

14:15Lindsay Pettingill:I mean, that's like most of tech, right? Or most of VC right there.

14:19Sherwood Callaway:Yeah. Yeah. It's like you'll take a W where you can get one. That's right. That's right.

14:22Lindsay Pettingill:OK. So Dev Bootcamp 2014. You're surrounded by folks who are different than you. Yeah. What was that part like? Did you have to do group projects?

14:34Sherwood Callaway:Absolutely, yeah. I think Dev Boot Camp was the first time I'd been to California. First time I'd been to San Francisco. Wow. First time I'd probably done yoga because they would do yoga at lunch breaks. It was a really hippie program.

14:49Lindsay Pettingill:Yeah, the Southerner.

14:51Sherwood Callaway:And you can imagine, I'm a Southern white frat boy. Yeah. Like, what is this? But I also never felt like I really belonged in that culture, and I loved it.

15:01Lindsay Pettingill:You were open to it, it sounds like.

15:03Sherwood Callaway:Yeah, I was really excited about it. I think I'd been looking for something different in California, and tech was something different.

15:09Lindsay Pettingill:Yeah.

15:09Sherwood Callaway:And I felt like I was really good at it. It was very creative. You know, I'd spent a lot of my adolescence, like, making music. And some of that music was digital, like digital audio production. So suddenly it's, like, completely expressive. I can use computers to make all of these apps. And it's not just, like, little snake games and a Python interpreter. It's, like, a full app. And it's got a YouTube integration. And I remember that summer, Node came out. I think Node came out. Maybe it was like version 1.0 or like an early LTS. But server-side JavaScript was new. We were learning Ruby on Rails at the time.

15:48Sherwood Callaway:Of course. So it gives you a sense of where the...

15:50Lindsay Pettingill:It's what Airbnb was built on for what it's worth. Yeah.

15:53Sherwood Callaway:Obviously, some people still love Rails. Shout out to DHH.

15:56Lindsay Pettingill:That's right.

15:58Sherwood Callaway:But it was a revelation for me. And from that moment onwards, I was probably 18, I realized I want to come work in an engineering role at tech startups in California. And I want to do my own YC venture-backed tech startup. And then I continued to chase that through the rest of my undergrad. It led me to Crunchbase after graduation. And as the junior most engineer at Crunchbase, you don't really get to work on any interesting features. So the one thing that was kind of left over for me to work on was our CICD pipeline.

16:29Lindsay Pettingill:Wow, sexy.

16:30Sherwood Callaway:And as you can imagine, like, here I am, infrastructure engineer, however many years later, 10 years later. Yeah. That's how it happened.

16:39Lindsay Pettingill:Wow. There are so many things to dig into there. One that I want to circle back on is a comment you made about programming being creative, right? VC is in tech. It's so full of hot takes and, you know, binaries, right? And one of those binaries, I think, for many years was, you know, we saw this ascendance of STEM degrees. And it was basically like if you're not doing a STEM degree, then you're probably, you know, you're making a terrible choice. And what's your future going to be going to look like? You studied history, as you mentioned. I feel like we've kind of swung back now to thinking more about history, thinking more about the role of creativity in what we build.

17:24Sherwood Callaway:There's a lot on that bone.

17:25Lindsay Pettingill:Yeah. Well, whatever you want to chew off.

17:29Sherwood Callaway:Yeah. Where should I start? I mean, I won't claim that a history degree is superior for engineers or for startups. I don't know if that's true. Certainly not for engineers. You could say that I spent my entire career peeling back layers, like having started at web development, wanting to go further, closer to the metal. And I really kind of stopped at Linux and infrastructure because that's where the market demands it. I became a founder around that time. So I'm not racking servers. I'll be forthcoming about that. But I've spent the last 10 years trying to learn the next layer beneath me. And I think that's not how everyone learns engineering.

18:12Sherwood Callaway:But for me, it really satisfied my curiosity because I kind of start with the layer of abstraction that allows me to do something cool. And then I want to do something a little bit cooler. And I'm like, well, the only way I can do that is apparently is I have to learn this next layer. And then you start operating at both of those layers and you now have more creative flexibility or leverage. And you can build something more impressive and then you run into a new barrier and you have to peel back the next layer. I think that programming is really creative and expressive. of, I'm a very visual person.

18:46Sherwood Callaway:And I think in terms of like systems and abstractions and shapes and like object hierarchy, like abstract and instantiated classes, systems of rules. And that's, I think it's a very different way probably than thinking about algorithms and data structures. In fact, like sometimes algorithms and data structures can be hard for me to grasp. But when we talk about system design or the design of a large code base or what's axiomatic about a code base, like what makes this, why does this file live in this directory as opposed to this directory? What are the truth, things that must be true about this file in order for it to live here instead of somewhere else?

19:31Sherwood Callaway:Those things come really intuitively. And it feels like kind of like molding with clay.

19:36Lindsay Pettingill:Yeah. Yeah. It makes sense that you describe it as creative. then, how does that show up in how you build your team, right? How, who you hire. I've met Justin a couple times, who's fantastic. Yeah, what's that relationship like for you all? Is he more, you know, capable isn't the right word, but does he thrive more in, you know, more algorithmic tasks? That's interesting.

20:02Sherwood Callaway:I don't know if I would say that that, like, those aren't the dimensions that we are complementary on. And Justin is my former co-founder from First Company, now founding engineer at Sazabi. Best friend, roommate, collaborator at four different companies, I think. Wow. We go way back. Yeah. And he's an amazing complement to me. I really could not be building Sazabi without him. One of the ways that we're very complementary is that I tend to be extroverted and I tend to verbalize, as I think. Justin is more introverted and more thoughtful and reserved feels like he's doing a disservice. He's not a shy guy, but he will, you know, he'll think about something before he shares what he, and he'll come to a conclusion before he shares that.

20:48Sherwood Callaway:I like to think throughout ideas by verbalizing them. So you often hear me like try on an idea by speaking it, and then I'll be like, oh, I'll walk it back. I say, actually, that's not quite what I meant, which maybe is not well suited for podcasts.

21:03Lindsay Pettingill:I'm not sure.

21:03Sherwood Callaway:But in that way, I think he and I collaborate super well. And we work well on problems. It's a nice counterbalance.

21:13Lindsay Pettingill:Does it manifest differently in, this is kind of silly, but even in PRs, do you kind of fire off? I mean, I know agents have changed all of this, right? But does he, you know, some people have, like, really stringent standards around, like, commit messages and, you know, they want to give all the context.

21:33Sherwood Callaway:And, I mean, you're working at a small organization now compared to Brex.

21:37Lindsay Pettingill:But, yeah, do you see it manifest?

21:38Sherwood Callaway:Like, am I firing off PRs and Justin's, like, you know, mine are, like, poorly tested and Justin's are, like, completed? That's not my implication, but maybe. No, I actually, I just don't think there's a correlation there. Yeah, interesting. But the way that we solve problems together as a team is that he will let me kind of generate ideas and basically spitball. And then he'll help reel me in or I'll help like prod or steel man some of the ideas that I come out with. And usually it will help like, you know, helps me come to a conclusion. And Justin will be sitting there like he knew the conclusion the whole time.

22:13Lindsay Pettingill:Perfect partnership. Yeah, it's great. It's a great team. I mean, we need people who I think will let us explore. Right. there is, I think, often this inner drive, right, to be heard or to go through that journey. So it's great that you have a partner who can help there.

22:27Sherwood Callaway:Yeah, I mean, without the right thought partner, like, I think that my advantages aren't very advantageous. Like, it's not very useful to be just generative without the feedback. And so, like, you need both sides of the coin.

22:41Lindsay Pettingill:Okay, let's jump to actually talking about Sazavia a little bit. It's a really exciting time for you. You just started YC for the second time, which I'm thrilled about in that I can't wait to see the – I mean, I'm already seeing the momentum, right? Just seeing the product continue to grow, obviously, customers and revenue coming for that. But let's take a step back and talk about the promises of Sazabi. We could talk a little bit about the manifesto in terms of like there are a couple of core claims that drive it and that are a little controversial. So let's let's spend some time there. I mean, just the first logs are all you need for folks listening who, you know, don't know about the space.

23:31Lindsay Pettingill:Frame that in terms of the space and also talk about why it's it rubs some people the wrong way. Yeah.

23:37Sherwood Callaway:I mean, well, for now, I think. Yeah. I think a lot of the core ideas behind Zazabi become less and less controversial the more that AI plays out. Because they seemed self-evident to me a year ago when I was writing about them. And now they're seeming increasingly obvious, which is great. I mean, it's very validating. I'm glad we got started when we did. For context, Zazabi is the AI-native observability platform for fast-moving engineering teams. it's effectively like Datadog but rebuilt in 2026 instead of 2010

24:11Lindsay Pettingill:yeah and walk us through what that I have an innate sense I mean it's almost repulsion strong word right like when you say that I physically know what that means

24:21Sherwood Callaway:there's a physical yeah actually much like credit to Datadog I think for a long time Datadog set the standard for product quality in this space they kind of defined observability or the observability era in the 2010s certainly defined the transition to cloud-based monitoring and helped us through this microservices period, which I think we're mostly past now.

24:46Lindsay Pettingill:Yeah, I saw you tweeted about that today.

24:48Sherwood Callaway:Yeah, yeah. Well, Twitter I just have a lot of fun with. But I think Datadog is still a loved product, but we also really liked VS Code before Cursor came out. I remember thinking VS Code had everything I needed. So there is a better way. And there's been a technology paradigm shift. And I think there's an ongoing paradigm shift in the way that we build software. And I think that the old way of finding and fixing issues in your production systems isn't just not going to continue to be the norm.

25:27Lindsay Pettingill:And walk people through that, right? I'm thinking metrics, dashboards. Describe some of, I guess, some of the pain, right, that you're responding to here.

25:38Sherwood Callaway:The three big ideas behind Sazabi are less is more, logs are all you need, and traditional monitoring is dead. And they just kind of point to, I think, the challenges that are associated with traditional monitoring, which I think all existed prior to AI and prior to Sazabi, but were exacerbated by AI. Um, less is more basically means that there should be less UI. Like there, if you open up Datadog today, you're looking at tens, maybe a hundred modules. Um, obviously all the, all the items in the sidebar, uh, all of the sub items in each of those menus. And then once within each one of those screens, like hundreds of configuration knobs and buttons.

26:21Sherwood Callaway:Um, so it's a complete overwhelm in terms of functionality and user interface, but also means less complexity. This flows into our second hot take, which is logs are all you need, but less instrumentation. This idea of logs are all you need basically refers to the fact that we, in contrast with the three pillars of observability idea, which has been dominant for a long time, We believe you only need to provide logs, not metrics or traces. It's not to say that instrumenting metrics and traces on your services can't be valuable, but just that it's unnecessary and superfluous. This is a very controversial idea because for a long time in observability, the three pillars, if the first idea of observability is that observability is about asking new questions about your system, things that you didn't anticipate, then the second big idea is the three pillars.

27:21Sherwood Callaway:And everyone just cargo occulted this idea. Observability vendors like Datadog have been, I mean, not to say Datadog or Observability is a PSYOP, but they've certainly benefited from the idea that you should be instrumenting more and sending more data and that you should have three modules or three sets of modules instead of just one. so you better believe that they latched onto this idea and then let it define their product roadmap and then sold it back to you. I think that logs satisfy all of the use cases that metrics and traces do. The original insight came from my personal experience. We had, at many companies now, I've bought and configured Datadog and configured all of the modules so all of it was available.

28:12Sherwood Callaway:But when something goes wrong, the first thing I always reach for is the log screen. And then I start doing log queries. And it just at some point occurred to me, like, I'm not using these other pages. And there's a huge amount of overhead associated with setting them up and maintaining them. And then that happened simultaneous with this realization that while logs used to be something that were, you know, disadvantaged because they were unstructured, You couldn't have a machine read them at scale. And then there was a constant push to make your logs structured. Like it was like at every organization I've ever worked at, it's like we've got an ongoing migration from unstructured logs to structured logs.

28:58Sherwood Callaway:And it's happening in perpetuity. And who knows when this migration will be complete. AI is now able to read that data at scale in a way that wasn't previously possible. And those logs are really rich. I mean, the information that's contained there, like the decision to, like the way that you write the error message, like whether it's like, this is a really bad error or like this is like, this seems suspicious. Like that has semantic meaning and value in it. And AI can actually use that. And then the last, I mean, I'm getting on a soapbox here with regards to logs for all you need. The last point I'll make here is that logs are essentially the same substrate as metrics and traces.

29:43Lindsay Pettingill:A log is an event, and a metric is just an aggregated event.

29:48Sherwood Callaway:And a trace is a collection of start and end events. So if you have the logs, you can reconstruct the metrics and the traces. And now you've only asked your customer, the user, to instrument standard out and standard error, which is way easier than StatsD or DogStatsD or Prometheus or Jaeger or trace propagation. It's way less failure prone. It's like the Occam's razor of observability. So it's just a better product experience and user experience.

30:20Lindsay Pettingill:So, yeah, there's so much to dig into here. I'm reminded of, you know, I was trained as a data scientist. Well, trained.

30:28Sherwood Callaway:I know, yeah, this must fly in the face of many of the principles that you know.

30:32Lindsay Pettingill:I mean, I spend so much time with logs, right, at Airbnb. And, you know, there are so many challenges with, again, pre-AI. So much of what we're doing with logs was, you know, cross-device logs and, you know, inconsistent practices across product teams. I mean, I'm curious to get your thoughts there. I actually haven't dug too deep into the, are there any tools that are making the collection of logs at scale easier?

31:01Sherwood Callaway:That's a great question. I mean, there are things like Vector. And honestly, I don't think that there's a ton of innovation in this area. And I'm not, you know, most people are still using OpenTelemetry Compatite logging libraries or log forwarders or log shippers. You know, there's probably some interesting work to be done on, like, the client side with regards to, you know, proactively filtering or aggregating logs that might, like, reduce the payload size or reduce the size of the amount of data that's stored ultimately in the end or just reduce the amount of network traffic or bandwidth that's consumed.

31:43Sherwood Callaway:I don't think that that's where the value is.

31:45Lindsay Pettingill:Yeah, clearly.

31:46Sherwood Callaway:I think AI allows you to do fuzzy everything. And what's great about that is that it's okay if you have one service that emits the service name with an in-sentence case and another service that does it in snake case. AI can resolve those two things for you. In the past, I think that we would have solved these issues by enforcing standards on teams. There would be like an observability team. And I know that because I've been this team where you go out to all the other teams and you kind of slap them on the wrist. And you're like, hey, man, didn't you read the guidelines for how to instrument your services?

32:23Sherwood Callaway:Like, or why are you instrumenting using your own framework instead of the framework that we built for you? And it's messing up all of our telemetry. And like now you can't correlate properly. Well, that we don't need to live in that world anymore. You know, we can have AI paper over these minor differences. We don't have to take on so much burden as product engineering teams, which is, it really is, there's just too much burden. The expectations for product engineering teams who have completely different incentives, completely different priorities are too stringent. Yeah. Well, and it's fascinating, too, to, you know, as I'm reflecting on what you're saying, you know, in many ways, it's like in situations where we don't have control, just psychoanalyzing a little bit, right?

33:12Lindsay Pettingill:Situation where we don't have control, we often try to take more control, right? And I think metrics, traces, all of this is a really fascinating manifestation of that, right? Because it's like, oh, my gosh, so much is happening between my services. No one ever really has a through line, right? And as much as we tried to create that, right, we tried to create it by just instrumenting more, right?

33:37Sherwood Callaway:You better believe the observability vendors love that, too. They're like, of course. Just one more. One more logging. One more log. And actually, that's a question. Sometimes people, skeptics, will ask, what if I don't have all of the logs that I need? And I think we've been really surprised. When you use Sazabi, you connect your code base as well. So Sazabi has access to both your log data and to the source code. We've been very surprised and impressed with Sazabi's ability to basically read between the lines. So if it has a log stream that goes through a code path that isn't fully instrumented, like you're missing log lines in certain code paths, it can assume or infer what has happened based on the source code.

34:26Sherwood Callaway:And it's usually right. We have other mechanisms where we try to encourage people to instrument more logs. Like we're working on a GitHub action that will add logs automatically to your pull requests or using the CLI to basically scan your code base and kind of give you some kind of score about, you know, like which parts of the code base are kind of like code coverage, like which parts of the code base are well instrumented versus not. But in general, I've been impressed at the agent's ability to infer what's going on, even in the absence of telemetry.

35:00Lindsay Pettingill:I mean, that alone is I don't think we can fully wrap our minds around that. Right. I follow some of the interpretability research that Anthropic, as an example, has put out. And hearing you say you're obviously not the only one who's like, oh, we noticed this thing. It can connect the dots, right? It can connect the dots in a way that actually is correct.

35:23Sherwood Callaway:Like a great staff engineer would do the same, right? They're like, I see that the log stream kind of stops here. But I know that what change recently went out, I can connect the dots there and draw a conclusion about what probably happened.

35:37Lindsay Pettingill:And in many ways, you know, that is the service that you're providing customers, right? Yeah. I mean, I know you don't use this marketing language, but, you know, it's, I think so many companies, what they're selling is, it's like, just imagine, right? You have this, it's almost like the rubber ducky problem in a way. Like, when I think about my time at Airbnb, there was one dad engineer who could answer all of my questions all the time. And I valued my time with him so much that I'd like save up my questions, you know, so So we could sit down and I could go through each of them. And now we get that on demand, which is pretty at scale, right?

36:12Sherwood Callaway:For every member of your team.

36:14Lindsay Pettingill:For every member of your team.

36:15Sherwood Callaway:Your executives can talk to that person as much as they want to.

36:19Lindsay Pettingill:Are you seeing that yet with Sazabi?

36:21Sherwood Callaway:I mean, I'm an executive and I use Sazabi all the time.

36:24Lindsay Pettingill:I mean, that counts. Dogfooding is, you know, incredible.

36:26Sherwood Callaway:I think we sell into CTOs and engineering teams. We have some sort of clever tricks to promote, like adoption from other parts of the organization. Like if a Slack user who isn't already signed up to your organization but is a part of your workspace mentions Sazabi and asks Sazabi a question, they automatically get provisioned an account. So it's designed to spread within an org that way and certainly to be used by operations, support, product. Even for executive use case, it can just be like, what new features do we need? or how is this high-value account doing? You can use it for product analytics, basically.

37:11Sherwood Callaway:I find that we use it for all sorts of use cases internally, although I go to market and position it as relative to Datadog because that's our main focus.

37:22Lindsay Pettingill:Yeah, the buyers are the same.

37:24Sherwood Callaway:Exactly. We're finding that it's serving a lot of use cases beyond that.

37:28Lindsay Pettingill:I mean, that is the beauty of the chat experience that we've all not reverted to, but there's something comforting in it, right? There is something kind of natural to chat, you know, back to ICQ or even, you know, Google chat back in the day.

37:48Sherwood Callaway:There are some other corollaries to this. Like, for example, one point of controversy we often run into is dashboards because people love their dashboards. personally I think that dashboards are dumb tell us how you really feel yeah no so we're we're just airing it all out um I think dashboards are mostly about vanity or they're about psychological safety so you either want that dashboard because you like it makes you feel good when you look at it or I guess I mean this is also sort of the same or you are nervous about the stability or performance of your application And the thing that alleviates that nervousness is like putting it on a screen so you can look at it at all times.

38:32Sherwood Callaway:I don't think that people find issues like new problems from dashboards generally. And I think an ideal instate is like you assume the product is working and your default assumption is operational. and it's only at down where you get alerted when there's something broken. So in that instate, which I think is the logical conclusion of all of this, you don't have a dashboard. You just have a staff engineer like Sazabi reach out to you and let you know, hey, there's a problem. This customer's affected and this is what it is and this is how you resolve it. But it's a tension that we're running into right now with the product where we're asking people to give up something that they've, these things that they've curated and managed.

39:21Lindsay Pettingill:And it's giving them comfort, like you said. Like, oh, I'm looking at the chart, right? Yeah, yeah.

39:27Sherwood Callaway:There's a tension between the world we think that people should live in and the world that they live in today and the Overton window and how we move them from point A to point B. It does show up in our product roadmap. Yeah, it's interesting.

39:38Lindsay Pettingill:I mean, when we first started chatting a couple years ago at this rate, I probably talked to you about my thesis, for lack of a better term, on headless BI, right? So, again, I was trained as a data scientist. And exactly as you noted, in many ways, my job was to make dashboards. And I was like, as soon as you make a dashboard, it's over, right? And so much of it was just doing that over and over and over again. And then you make it and someone looks at it and never comes up again, right?

40:09Sherwood Callaway:And so... Yeah, I mean, you're wearing the Hex sweatshirt right now. I am. Hex is kind of solving this for data analytics.

40:16Lindsay Pettingill:Yeah, and in many cases, like Sazabi, they've always been ahead of the curve, right, in terms of, I think, taking product risks where other people wouldn't, right? Which is, you know, it's always great to have those examples. But, you know, I had this thesis, which is panning out, I guess, in various ways around, like, don't make me do the work, right? Like, don't create a product where it's my job to, you know, go to a UI. It's my job to do the thinking in some ways, right? When all I'm doing in many ways, so much of dashboarding work is about anomalies, right? It's anomaly detection. You know, maybe you set some parameters or something, but it's like, you know, that's how we did it 10 years ago.

41:05Lindsay Pettingill:We're so far beyond this now. And just this idea that, you know, we should be meeting users where they are, which is often in Slack, right? It can be on WhatsApp, you know, iMessage, whatever. You know, for me, it feels very natural. Again, don't make me do the work. You have all the data, right? Like, you have access to my code base. I've set, you know, thresholds. come to me. And I'm really intrigued by this comment you made that the market might not be fully there yet. I'm curious, where are you seeing folks get really excited about it? Are you noticing, are there other trends that you see with these customers who just, lack of a better term, are they AI native, where it's like they're used to this and other facets of their work?

41:53Yeah.

41:54Lindsay Pettingill:Do you see any trends so far? Yeah.

41:56Sherwood Callaway:That's a great question. I mean, We focus on selling to like series A and series B companies. We find that kind of like earlier stage companies tend to be more AI native and tend to have more appetite for AI tools and for like novel approaches. I think these companies are basically, I mean, obviously they have fewer established tools and processes. I think they're also just looking for alpha. They want to find a way to accelerate. And one of the things that feels slow right now is like maintaining production and fixing bugs.

42:25Lindsay Pettingill:So talk about the self-healing aspect of this, right? Because that's on your roadmap as well. That would be a huge unlock. Yeah. Walk us through what the vision is there and what it looks like in practice. Yeah.

42:40Sherwood Callaway:It will be a very strange world, I think, when it becomes widespread. But Sazabi's mission is to be the default observability solution for companies of all sizes during the AI era, which we define as 2025 and beyond, so the year of agents and beyond. And our vision is a world where software heals and improves itself without human intervention or direction, which basically is self-healing software.

43:07Lindsay Pettingill:Not ambitious at all.

43:09Sherwood Callaway:Yeah. I think in that future software looks kind of organic. Self-healing can probably be defined as like a software that changes itself in response to some stimulus in production, probably like an outage or a bug or an error. You could argue that we've already had self-healing software in the sense that we have automatic rollbacks. Some teams have automatic rollbacks. I think it's still mostly like a holy grail, kind of like preview environments. You should be so lucky that you work at a company that has one of those. That is a pretty weak and uncompelling version of self-healing software. and it doesn't do justice to what we want to build.

43:53If you think about nature, when things heal,

43:57Sherwood Callaway:it doesn't always mean we're returning to a previous state. A bone breaks and it heals stronger than it was previous. Or you repeatedly strain a muscle over your lifetime, it becomes developed. Or over generations, it becomes even more developed. I think that the world of self-healing software will look like that, where software changes and evolves and becomes more robust, and maybe it even develops new characteristics or features, mutations, if you will, in response to production usage. That's the world that we want to build with Sazabi. I think it requires access to production data and the ability to interpret and analyze that production data and feed it back into the rest of your software development lifecycle.

44:42Sherwood Callaway:So I think Sazabi kind of represents the last link that allows us to create that.

44:48Lindsay Pettingill:How much are you thinking about the next model releases, right, in terms of your product roadmap, in terms of that vision, right? I mean, I don't know if you're thinking in terms of, you know, if you have a timeframe and it's already taking this into account. I mean, none of us obviously know actually what's going to happen, right? But it is a tension, right? You have to build for where we are today, even if in six months the world, in terms of what Sazabi and all of us as builders are capable of doing, is not predictable.

45:22Sherwood Callaway:Yeah, I mean, it's an anxiety-inducing prospect. I think I was thoroughly AGI-pilled, whatever that means, when I initially came up with a premise for Sazabi and was totally convinced that all of these little bells and whistles like dashboards, flame graphs, service maps, even metrics and traces were superfluous. and that in a world where we have cheap, abundant, and performant AI models, we won't need them. And so that's what led to our key features, which are the idea that you don't look at your telemetry directly. You only debug things through conversation. You just ask an agent what's wrong.

46:11Sherwood Callaway:And the idea that you can't create monitors. Instead, you just receive agentic alerts or autonomous alerts, which are entirely agentic in the sense that the agent is looking for anomalies, investigating them, deciding whether to escalate them to you. There's no way for you to build in a particular learning condition. Now, there's an asterisk there, which is that you can tell the agent to look for issues in particular parts of your system or to have a higher sensitivity. So maybe you have like a payment service, I can say. Zabi, anytime anything weird happens in payment service, make sure to let me know, and that will change some of the alerting behavior.

46:54Lindsay Pettingill:So I want to get to brand, because I think that what you all are doing is pretty special and fun. But before that, going back to what you were just saying, are there code bases, challenges, I guess you name it, that Sazabi is particularly well positioned to fix, solve, self-heal? Do you have a point of view on that? Yeah, that's a great question.

47:27Sherwood Callaway:I would say that we're kind of discovering that as we go. I wish I had a more satisfying answer than this. It's a little bit vibes-based. In the same way that I think people are discovering what types of code bases and technologies agentec coding works well for, we're also discovering what types of code bases and technologies and tech stacks and service architectures are easily for us to investigate, monitor, root cause. We intentionally seek out customers that have weird stacks or that build, like maybe this customer is building a piece of infrastructure, like hosted Postgres or something like that, that we haven't really served at large scale before.

48:08Sherwood Callaway:And we want to see how Sazabi performs on that use case. So we don't have, I wouldn't say that there are specific stacks that we think Sazabi works well for right now. this also feels like a little bit like it's not immaterial. Because again, if you assume a certain rate of model improvement, then you can assume that for any code base, any tech stack, any service architecture,

48:35Lindsay Pettingill:Sazabi is going to be effective at root cause analysis and detection.

48:39Sherwood Callaway:And we do assume the models are going to continue getting better. I think it's a basic premise probably of what we're trying to build. We're trying to build observability for late-stage AI.

48:49Lindsay Pettingill:Yeah, super powerful. Okay, Brand, you all launched your website, what, a week or two ago, and it's honestly unlike any other that I've seen. For better or worse. Yeah, I mean, it's bold. Yeah, talk about your website. Yeah. And maybe we can get to the name a little bit as well, right? I'm always learning new things from you. I obviously had to look up what Sazabi meant before I invested. You know, really critical diligence point right there. So, yeah.

49:26Sherwood Callaway:We're going to out me as a massive nerd. Exactly.

49:29Lindsay Pettingill:I mean, we started there, so, you know, it's fine.

49:31Sherwood Callaway:Well, I guess the website is a sort of an immersive experience where you are in a kind of like a mech suit or like a pilot seat. and you're looking out over a city during nighttime. And on different buildings in the city, there are indicators that indicate issues with the city. So there will be a red light that says there's some 500 errors here. There's a green light that says this component is operational. And there's a yellow light saying there's a latency trend that looks concerning. And you can interact with them, and you'll see the dialogue between yourself, yourself, the operator, and Sazabi, root-causing them.

50:13Sherwood Callaway:And you get to click on little buttons to help proceed to the next phase. And then below that, we have a more conventional website. But I will say that I still think the brand really shines through in the rest of the website. The textures that we use, the bezels, the illustrations, the graphics, the typography. There's even, we have scan lines across most of the site, which gives it this kind of, sort of a Blade Runner vibe and a sense of texture that other websites don't have. On some of our header typography, we have a subtle glow or gradient inside of the typography itself.

50:53Lindsay Pettingill:And did you drive most of that? Where did that come from?

50:58Sherwood Callaway:I've worked with two studios. On this project, I worked with one main studio. and I think when I brought the initial concept of the brand to them, they loved it. These guys are just equally nerdy, I guess, and they really ran with it. And I think I have to give them a ton of credit for bringing it to life. I've created mood boards. I created early versions of the brand on my own that I brought to them. And I think that there were specific visual elements that I loved and wanted to incorporate. A lot of them come from video games. The glow around the typography is something that I saw in Call of Duty Black Ops, which I thought looked really cool.

51:38Sherwood Callaway:Black Ops also uses layered textures and illustrations, which are really cool in some of the backgrounds. It's very maximalist in a way that I think is a different encounter to a lot of design today. Certainly, it's not consistent with sort of the Shadzian slop world that we live in today or the post-linear design. I'm not sure what to call it. It's like authoritarian design world where everything has to be clean and minimal.

52:12Lindsay Pettingill:Say more about why that's important to you. Not that aspect in particular, but the whole project, right?

52:17Sherwood Callaway:Yeah. I mean, Sazabi is a personal passion project for me.

52:20Lindsay Pettingill:Like, I had one investor describe it as my tombstone company, and I thought that was an amazing way of describing it.

52:26Sherwood Callaway:Because this is like the company I want to be known for. I don't plan to start another one. I think, you know, I called it Sazabi because when I set out to start another company, one of the first things I wanted to make sure was true was that it was fun. I grew up a massive Mobile Suit Gundam fan, and I continue to be. and in Mobile Suit Gundam, which is this 1980s sci-fi anime franchise, there is a mecha mobile suit that the antagonist pilots called the Suzabi. And it's just a really cool, red, futuristic suit. It's very powerful and fast. And I thought, like, that's just, like, cool. That thing makes me go, hell yeah.

53:07Sherwood Callaway:And I want, like, you know, there's no observability tool that makes me go, hell yeah. I want to build a developer tool that makes people feel that way. And I wanted it to be fun. And so it was almost a symbolic act was to choose to call it or name it after something that I love.

53:21Lindsay Pettingill:Yeah. I mean, it's bold in the best way. And I think, you know, looking, thinking back to something you said a bit ago around, you know, tech engineering is creative.

53:34Sherwood Callaway:Right.

53:35Lindsay Pettingill:I don't think it is for all people. It clearly is for you. Right. In terms of what you bring to it, why you bring what you bring to it. What have been other developers' reactions?

53:46Sherwood Callaway:It's divisive. Yeah. I mean, I think starting with a name, some people love it. Some people hate it. It sounds like Wasabi.

53:56Sherwood Callaway:I've gotten into the habit of spelling Sazabi. So I work at Sazabi, S-A-Z-A-B-I, which is totally fine. We have our.com domain, so I'm happy. We have all of our OG handles on different platforms. I'm not too concerned about that. You know, Shakespeare said, what's in a name? You know, like, they're great. You know, bring it back to music. Like, so many great bands have ridiculous names, Coldplay, Radiohead. Like, they're great because of the, you know, of the bands. You can remember them, right? And I'm certain that, like, Sozabi will be the same. The brand is also divisive. I think, you know, it's very red.

54:30Sherwood Callaway:And, like, red makes people feel a certain way. I'd much rather break through and to have an opinion than to not break through at all. And I think we're much more likely to attract a following or for people to be excited about using Sazabi or working with us or about being associated with our team or our brand if we have an opinion and a voice. And so I'm not concerned about that.

54:58Lindsay Pettingill:So did it feel, was it an active choice on your part? Meaning, obviously it was an active choice, but do you feel pressure to shift anything, you know, by investors, by...

55:11Sherwood Callaway:No, I mean, I guess we do focus on serving like startups, like early stage and mid-market, like high growth startups. The main reason for that is because, you know, I've worked at high growth startups my entire career. I think the largest company I've ever worked at was probably 500 employees, which is Brex. And I just wanted to build a tool for people like me or for engineers who worked at those companies. It's like those are the types of companies I could confidently sell into. I understand their priorities. So it makes sense for me as a target or initial target market. I also think that a lot of new AI observability-focused companies are focused on enterprise.

55:48Sherwood Callaway:Datadog is very definitively focused on enterprise. So there's this nice opportunity to serve this segment. Startups, I think, are, you know, if I were selling it to enterprise, like, we might need to have a little bit of a different brand. Fortunately, we're not.

56:02Lindsay Pettingill:Yeah, yeah. You know, we're selling to startups.

56:03Sherwood Callaway:And I think, you know, Hex is an amazing brand. Like, another shout out for that and their team. But it's also different. It's one of the luxuries, I guess, of serving this particular market.

56:15Lindsay Pettingill:Yeah, I mean, and as an investor, you know this about me, but, you know, in general, I'm... Thank you. I'm so obsessed with slash one of the most important things for me is just finding people the point of view. Right. A point of view these days is harder than than anything else. Right. Like, as you noted, the slop, you know, the information environment is just full of, you know, regurgitated thought, sloppy writing. And so I do feel like a big part of my job is cutting through and finding folks who have a strong opinion about a product that needs to be made, that needs to exist in the world, a problem that keeps them up at night.

56:55Lindsay Pettingill:And it's because I primarily invest in data dev tools. Like you said, it's even rarer to find that POV shows up there. So it's a welcome change. Going a little deeper into the developers that you sell to, you have had a really interesting angel investor strategy. I think it's one that many people could not pull off, but I think they strive to. So just talk a little bit about what the angel strategy is, how you executed on it. And what brought it to mind is actually the part of your website where you – actually the previous iteration where you had folks in Tony Stark suits. So, yeah, tell us more about that.

57:40Sherwood Callaway:We wanted to do that again for this version. We had to cut some scope. I guess the – just to share context, we have over 100 angel investors on our cap table. They're all on roll-up vehicles, so future investors can feel comfortable knowing that our cap table looks quite clean. But these people are typically founders, CTOs, CEOs, technical leaders at basically the best AI and developer tools startups in the world. Companies like BrowserBase, Replit, Vercel, Daytona, Graphite, many others. The strategy here is that, you know, I'm a big believer in like creating, I mean, here we are at Village Global, sort of creating a village.

58:29Sherwood Callaway:I want as many allies as possible. I want people to be bought into my success and to the company's success and to take them along for the journey. Some of the investors in Sazabi are investors that I worked with on my previous company. I think like the angel investors are a way for me to consummate that relationship and to say, hey, you're a part of the team. Sazabi's going to succeed with you and because of you, and you'll be a part of that story. It's not as transactional as me thinking, because you work at this company, we will get a pilot at that company, although in some cases it does play out that way.

59:08Sherwood Callaway:People move companies, so we don't always get to be executed on it in that fashion, but certainly it happens. I think early on, it was just me and a long memo and a vision and some strong opinions. And I wanted to basically sell this idea and this vision in the absence of a team or product. And one of the ways I could sell to the companies that are my dream accounts before I even have anything in hand is to sell them on the vision and on me, the founder, and to bring them in as angel investors. And I think it's created opportunities for us.

59:45Lindsay Pettingill:And who are the best angel investors, whether you can give their names or how do they show up? So we get lots of founders who listen to this content that we produce and they're always looking for advice, right?

59:58Sherwood Callaway:Well, one piece of advice I'll share is I generally only take money from people I've met in person. I think there's a lot of money in Silicon Valley. And if you're a sought-after company, you're going to have lots of people who want a piece of the cap table. I think you should like your investors, and you should also be responsible about diligencing them. Because you want to make sure that you're in bed with the right people, people who share your values. So that's definitely a recommendation I would make to everyone. In terms of best angel investors, I love having someone I can text about anything.

1:00:40Sherwood Callaway:I've got 100 people on my cap table, like someone who's an operations leader or someone who's a founder of a post-exit dev tools company or someone who's a series A company, so they're just two steps ahead of where I am. Or someone who is more in infra and someone who is a buyer at another tech company that isn't in infra. But when you have this many angels, you have someone you can ask for a favor or for advice in any position. That's really nice to have that. And ideally, these relationships are close enough where you have each other's phone numbers. Totally. You're going to happy hours together.

1:01:17Sherwood Callaway:Yep. And these people become friends and generalist reporters. I, you know, it's obviously great when you've got angel investors who are actively trying

1:01:27Lindsay Pettingill:to bring you into accounts or trying to promote you.

1:01:30Sherwood Callaway:That's not my expectation. I do think it's, you know, maybe one of the big things I learned from being a second time founder is that like you should like your investors and you shouldn't hesitate about asking for favors.

1:01:42Lindsay Pettingill:Yeah.

1:01:43Sherwood Callaway:I think a number of times I've asked you for things. Yeah, no, you're great at it. Consistently come through. But as a first-time founder who's a little bit younger, less experienced, you may be a little bit more shy about reaching out to your investor. You should make them work for you.

1:01:55Lindsay Pettingill:Definitely. Yeah, why are they there otherwise?

1:01:57Sherwood Callaway:Make them record podcasts with you.

1:01:58Lindsay Pettingill:Yeah, there you go. What is the most annoying thing about selling to developers?

1:02:04Sherwood Callaway:Most annoying thing about selling to developers? I mean, developers are such skeptics. For, like, the people who occupy the very beginning of the adoption curve, they're still so skeptical. They also think that they're immune to branding and marketing. They're totally not.

1:02:23Lindsay Pettingill:Say more.

1:02:24Sherwood Callaway:Well, I mean, maybe Suzabi's brand will just totally flop it. We'll discover that they were right, but I don't think they are. I certainly am not. I want to use developer tools that make me feel cool. I think developers hate to pay for things until they've seen value, which makes anything that's sales-led really hard.

1:02:47Lindsay Pettingill:You just kind of have to do product-led, which has a whole bunch

1:02:52Sherwood Callaway:of strings attached and considerations for how you build your product, how you build your business, how you go to market, how you deal with competition.

1:02:59Lindsay Pettingill:Any lessons you can share there that you've learned so far in terms of time to value? Are there any like aha moments that you've had, processes that you've changed? Naturally, we could get into onboarding, but yeah, I'm curious to hear your thoughts here.

1:03:14Sherwood Callaway:Yeah. I mean, Sysabi requires you to connect a few different things before we can provide the most of our value. For example, we ask you to connect your code base, so like a GitHub connection. We ask you to install the Slack app so you can communicate with Sysabi over Slack and receive apps. It's not required, but you're going to get a lot more value if you take those two steps. And then last but not least, we ask you to send us your production logs. So we're asking a lot before you...

1:03:44Lindsay Pettingill:So logs are not all you need.

1:03:45Sherwood Callaway:I mean, logs, you've got to have some integrations too. Sure. But I think one thing we've discovered over developing the product and rolling it out to some early customers is there needs to be some trust and value delivered early. One of the ways that we've solved for this is you can use Sazabi with what we call an external back end, meaning you can have Sazabi's agent and alerting system operate on top of a third party logging storage system like Datadog or Axiom or ClickHouse or Century or PostDog or any one of many other logging back ends. And what that does is just lower the barrier for adoption.

1:04:24Sherwood Callaway:You don't need to actually send us any data directly. You can just plug in an API key and start seeing what it's like to use Sazabi and getting some of the value. Of course, Sazabi is way more powerful when you use R logging storage. It's also cheaper because you wouldn't be paying for data log storage while also paying for Sazabi inference. So I would say that we've had to discover and implement little features like that in order to unlock value at earlier points in the customer journey for developers. And then meanwhile, we try to support both product-led and sales-led motions. when we approach later stage customers and it's more of a sales-led motion, the bar for adopting a new observability solution is quite high because this is something that needs to be very reliable, needs to be available and useful in the event of a production outage, which is like the most, like this is like if you're bleeding out, it's your support tool.

1:05:31Sherwood Callaway:And so I think the requirements for adoption there for later stage customers are pretty high. So one thing that I think gives me some peace of mind is that Zabi's had to invest a lot in infrastructure security and compliance. And that's not something you can vibe code. So for now.

1:05:53Lindsay Pettingill:Okay, so Facebook had their seven friends, right? It's basically canon in tech, right? The idea was once you get to seven friends, you're basically hooked. You're not going to turn from the platform. How do you think about that at Sazabi, right? Is it?

1:06:08Sherwood Callaway:Is there some sort of network effect or viral?

1:06:11Lindsay Pettingill:Well, more like is there something that Sazabi can tell? Oh, is there a sticking point? Yeah.

1:06:16Sherwood Callaway:Yeah. That is a great question. I think once you start receiving autonomous alerts, it becomes clear how powerful this is obvious and how useful it is. Because just by connecting these things, not by doing any configuration or setup in the platform, like you said, we're bringing the value to you instead of expecting you to buy the platform and then do hours worth of investment. Once you start getting those alerts, I think that's usually when people have an aha moment. Oh, my gosh. I've put in close to zero effort. Right. And I have higher signal, more actionable, richer alerts than I've ever had at any previous software developer role in the past.

1:07:00Sherwood Callaway:I think generally we focus on the connection of Slack, GitHub, and having production logs flowing. Because those are the three things that once they're in place, you're really getting maximum value. Yeah.

1:07:12Lindsay Pettingill:Yeah, I mean, it's been, you know, on Slack in particular, it's been wild. And I guess it's not at all surprising, but, you know, at Airbnb, we were one of the very early users of Slack. And I was new to tech. Airbnb was my first tech job. I had come from finishing a PhD. You know, it's kind of nothing further from tech. And I just remember, you know, Slack just being like, what? I'm supposed to show up here and just have conversations, you know? Like, you know, it just was – I couldn't wrap my mind around it. But we were such avid users that obviously I got on board. But, you know, fast forward then to today where, you know, it's literally where work is getting done.

1:07:49Lindsay Pettingill:Even when I go on vacation, I can't, like, take Slack off my phone, right? It is the lifeline. So I think it makes a ton of sense that you meet users where they are there.

1:07:59Sherwood Callaway:And it's just one of many, like, chat platforms we support or plan to support. It's just the one that is, like, has, like, almost 100 % overlap with our ICP today. Yeah.

1:08:11Lindsay Pettingill:Yeah, I love, I hope it doesn't get shut off, right? Just in terms of building with Slack is fun, right? Yeah. For tools like yours.

1:08:18Sherwood Callaway:Well, they have, I mean, I think their documentation could do some work and like the app approval process is quite painful.

1:08:25Lindsay Pettingill:Yeah.

1:08:27Sherwood Callaway:But they are rolling out some pretty cool and interesting new features to support agents. It's much easier to stream messages into Slack or stream status updates or tool calls into Slack response than it would have been previously. I think the previous mechanism would have just required repeated updates to the same message. So I think we're still, I actually am not seeing those features widely used right now. So we're in the early days probably. But I'm sure Slack is not going away. Probably mostly because of the Slack Connect feature. The network that it creates between organizations.

1:09:02Lindsay Pettingill:Definitely. To get critical, like what's the, I always like to ask about pre-mortems, right? So if Sazabi were not to IPO, if it were not to become the standout in our existing fund and many others, why not? What's the story you'd write today to predict that? And obviously, this can touch market.

1:09:31Sherwood Callaway:I can think of a few causes of death. One of them is maybe not predicting the rate of model improvement correctly. Either that stalls or it advances at a rate faster than we had planned. And then I think if models don't get better today, then there's probably still a lot of post-training and RL that we can do, evals that we can create. I think our product is mostly still viable. But if models, let's say models get twice as good or five times as good, like that will probably, like I can imagine that might invalidate some of what we've built or even like the way just the software development, it would transform the software development lifecycle.

1:10:16Sherwood Callaway:So much so. So much so that like it's unrecognizable.

1:10:19Lindsay Pettingill:And that would mean that the type of observability that you all, like observability as a whole wouldn't be as necessary?

1:10:28Sherwood Callaway:There's one future I can think of, or two futures I can think of. One is a world of just-in-time software, where all of the software that is created is created on an ad hoc basis for a particular session, used and then thrown away. And the model generates that software. That could be either code or in an even more futuristic and bizarre version would be a generator of UIs where the pixels themselves are being generated, which we saw Anthropic do a proof of concept for almost like a year ago. That's a world where I think observability doesn't make as much sense because you're not maintaining software, like long or persistent software.

1:11:13Sherwood Callaway:Maybe observability takes on a new meaning where it's a focus on observing models and agents. Another future is one where there's just zero software and interfaces go away entirely and everything we do, we do through an agent. I think this one is less likely because humans still love to see and click things and drag things. Even as we use chatbots, it's useful to have a button that says, accept edits. But those are two worlds where maybe observability as we know it is completely obsolete. That, I think, much more likely is a world of abundant software or infinite software, where the amount of production software that is written and deployed and runs in perpetuity just continues to grow at an exponential rate or greater than linear rate.

1:12:06Sherwood Callaway:And the only way we can effectively monitor it is with AI or agentic observability, platforms like Sasabi. So that's one potential risk. I think there's competitive risk. Obviously, other companies are focused on automating software development lifecycle. They're generally focused on different parts. Anthropic has cloud code, but I think mostly they're focused on model development. Cursor and Composer 2, and they, I think, increasingly do model development, but they also live in the middle stage of the software development lifecycle now. They purchase Graphite. They have BugBot. They have PR ReviewBots, which is like one step before deploy, and then after deploy comes observability.

1:12:55Sherwood Callaway:So I think there are other companies that are – fortunately, they have other focuses, other core competencies. So I think you'll want a solution that or the company that will win in this space will be explicitly focused on observability and on detection and root cause analysis. Also, like, just building great storage for logs, like multi-region, high availability, high durability, low latency storage.

1:13:23Lindsay Pettingill:And you guys are already thinking about that.

1:13:24Sherwood Callaway:Which we already have. Yeah. Is, like, a hard problem. And making that cost effective is a hard problem. So I think it's just like a big, it would be a big scope for one of those teams to take on and do well. But that keeps me up at night. Obviously, like the market turning, I think we live in very funny times with geopolitical risk and the price of oil and the war in Iran and the war in Ukraine. It's unclear like where the market will be in three months, let alone six or 12 months. So there's, I guess, a potential for just a venture market winter or an AI winter that could be damaging. Maybe the cost of inference goes up to a point where the economics of this solution don't make sense.

1:14:19Sherwood Callaway:Obviously, energy is becoming more expensive and scarce. So that's something I think would potentially make something like Sazabi non-viable. I think all things considered, there's not that much I can do about the meta venture risk. And I feel pretty good about AI. It's getting better at a rapid rate and has been for a while. I don't think that there are many other teams that are as well positioned to do this that have our particular product vision and our singular focus. So I would say that our odds are pretty good.

1:14:54Lindsay Pettingill:Yeah. So much of my conviction here, you know, was about you, right? And you and, you know, everything you're bringing to this, but also the tailwinds are so clear, right? Particularly in terms of the models, particularly in terms of the benefits that you have as an AI, like building this company now versus building this company two, three years ago, right?

1:15:15Sherwood Callaway:Yeah.

1:15:15Lindsay Pettingill:There's no ship to turn, right? You can build and I think adapt a lot faster than other folks. So it's exciting.

1:15:22Sherwood Callaway:Yeah, I mean, everything that we wrote about in the memo, like everything I, when I go, I don't look at this often. When I occasionally have to, I'm struck by how right it is. And I think we actually opened up on this note, which is like the, just the things that were counterintuitive or non-obvious six or eight or nine months ago are becoming more obvious, which is very validating. It means that we got started at the right time.

1:15:51Lindsay Pettingill:Absolutely. And we see it all the time that companies are too early, right? You can be right, but too early, which means you're wrong. Everyone makes those mistakes because venture is a craft at best, I think. And predicting the future is what we all try to do. It feels better when the stars align, of course.

1:16:16Sherwood Callaway:Yeah. We were a little early on Healthcare Voice AI with our previous company. And so I know what it's like to miss the boat. And then we were late on other things. There were health care regulatory opportunities. I feel like we missed. So one thing that helps with predicting the future is being a subject matter expert in your space.

1:16:34Lindsay Pettingill:Totally, yeah.

1:16:34Sherwood Callaway:Great piece of advice. Yeah, exactly.

1:16:36Lindsay Pettingill:But I think, you know, if you look at like, you know, Paul Graham's essays from years ago, probably over 10 years about like, how do I come up with a venture idea? Right. In some ways, it's like, you know, what's stuck with me from these pieces that are many years old? Right. Okay. Schlepp work. Right. Like do something dirty. Schlepp blindness. Yeah, exactly. Like do something dirty and unsexy. You know, it's, I mean, it's actually one of my favorite essays in venture. And it's a little blind to exactly what you're able to lean into, which is the domain expertise. Right. And I think especially today, as we see the, what's required to build, right?

1:17:13Lindsay Pettingill:What we need has just the ceiling. I always forget, right? It's a lot easier to build than it used to be. I won't mix my metaphors, right? And because it's so much easier, you know, in many ways I do see and I hope for, and we're seeing early signs of it, right, some renaissance of if they're, you know, I don't know if that's the proper word, but, like, you can imagine all sorts of domain. Domain experts are the ones to win today, right? They should be so much better suited. Speaking of which, your dad. Your dad is an orthopedic surgeon? Is that correct?

1:17:45Sherwood Callaway:Yeah, I've retired now. He's been retired for about a year.

1:17:48Lindsay Pettingill:Okay, so he's no longer doing surgeries? Is that what that means?

1:17:51Sherwood Callaway:He's no longer doing surgeries or office visits, clinics. Okay. So he's out. Okay. It took a long time for us to get him there. Yeah, I can imagine. Because he's a workaholic and loves what he does.

1:18:02Lindsay Pettingill:Yeah, and orthopedic surgeons, as you know, I've had run-ins with them. I got hit by a car, broke my leg. These guys love doing surgeries. Yeah, yeah. They love fixing bones. Um, how I've, I've heard rumors that he's, uh, or maybe I've seen this on Twitter that he's getting into vibe coding. Uh, tell me what, uh, what's going on here.

1:18:24Sherwood Callaway:He's on his own, uh, IT programming and computer science journey. Okay. Um, I, well, he, uh, one thing he did when I was, uh, I guess probably as far back as college or high school was he discouraged me from going into medicine, which is really interesting. You know, I think.

1:18:41Lindsay Pettingill:What was that about?

1:18:42Sherwood Callaway:I don't want to, I can only speculate about his psychology, but I think my dad would have been a great business person, but he comes from a family of lawyers and doctors from East Tennessee and maybe had a certain set of conservative values built into his, I mean conservative, not in the political sense, but like... Risk-taking. Risk-taking, the appetite of risk and what's a respectable or responsible. career or adulthood look like. I think he regrets some of that decision because he's, I mean, he's at the top of his, or was at the top of his field and has been very high performing. And I think has just had to work very hard for a long time and has seen other people that maybe did not work as hard as he did do much better than he has done.

1:19:34Sherwood Callaway:And people who are like interested in similar things. He was buying computer magazines when that was the thing. He was doing homebrew kits. Really? Yeah. He's always kind of had a technical bent.

1:19:48Lindsay Pettingill:And now he's buying Mac minis, or what's it look like?

1:19:51Sherwood Callaway:That's so funny. He was sending me OpenClaw videos and telling me, sure, I'm going to buy you a Mac mini for your birthday. And I'm like, Dad, I've already got a Mac Mini.

1:20:01Lindsay Pettingill:Yeah.

1:20:02Sherwood Callaway:Come on. Do you think I'm an amateur? I guess it started, I think his curiosity was piqued when I was into online video games as a kid, and I asked if I could build my own gaming PC. And so now I still have a NVIDIA GeForce 760 box in my bedroom. How much does it cost?

1:20:22Lindsay Pettingill:Do you remember? Was this like a...

1:20:24Sherwood Callaway:It was probably, I'm going to guess it was$400 or something. It was pretty big. It was by far the most expensive part of the rig. Right. I think he could see that there was something positive there. And he kept you off the streets.

1:20:34Lindsay Pettingill:He kept me off the streets.

1:20:36Sherwood Callaway:I was addicted to something else called a World of Warcraft. Another kind of drug. And so he, you know, to his credit, encouraged it and then encouraged me to go to try this web development boot camp when I could have, when it wasn't clear, like there would be a real payoff. Yeah. And then as my engineering career got started, I think he found that very interesting and was excited for me and wanted to be able to talk to me about the type of work that I was doing or understand what I was building. And that led him to take some online computer courses at a Wake Tech, which is the local technical college.

1:21:16Lindsay Pettingill:Is that Wake Forest? Nope.

1:21:19Sherwood Callaway:It's not Wake Forest. I think it's just Wake County Technical College. But Wake Forest is nearby. And now in retirement, he's had a lot more time on his hands. He's been able to go a lot deeper. And he's probably done four or five courses at this point. I don't want to. He'll be upset with me if I undersell. Because he's worked very hard on them. And he's built some impressive applications. Like he's built full-stock applications, deployed them into the cloud. A lot of the technologies they're teaching are technologies that are a little bit hard to use that you would probably not reach for today, like VMs.

1:21:52Sherwood Callaway:So he really knows his stuff. He's taken AI courses on sort of traditional AI with CNNs.

1:22:03Sherwood Callaway:And he's learning AI concepts that actually even predate me. So it's fun to sort of trade notes. Then more recently, as agents have become popular, I've taken the opportunity to kind of show him how he can use things like Cloud Code to redo all of the things that he's learned in the past, over the past year or two. And at first he was, I think, intensely frustrated because it's like, what the heck? I just spent two hours debugging my PyCharm IDE. And it took forever just to get this simple app working and Cloud Code is just one shot at it. But then I think he's now at the point where it feels like a creative unlock for him.

1:22:52Sherwood Callaway:He's able to build so much more. It creates this amazing learning, rewarding feedback loop that he's really running with. So he sends me projects that he works on. He sends my sister projects. We're in a group text. My younger sister is an engineer as well. It's mostly him sending things to us.

1:23:11Lindsay Pettingill:So did he ever get onto the Mac Mini? Is he on VMs now?

1:23:16Sherwood Callaway:I think he's got some stuff running in the cloud. I'm not sure if he's bought himself a Mac Mini. For a long time, he was taking his computer science courses on a Lenovo ThinkPad. And I was like, Dad, we've got to get you out of PowerShell. Just wait until you get a MacBook.

1:23:30Lindsay Pettingill:Trust me.

1:23:31Sherwood Callaway:Trust me.

1:23:33Lindsay Pettingill:That's awesome.

1:23:34Sherwood Callaway:And it's been really fun. Recently, his passion has been OpenClaw. He's really excited about it. And I think he's been amazed at what, like, the amazing, like, it's just the incredible use cases and how people are running and building and running entire businesses using OpenClaw.

1:23:50Lindsay Pettingill:Yeah, yeah. Yeah, it does make you wonder how his, you know, again, I don't know much about his career practicing medicine, but what would have changed, right, if he had access to OpenClaw, right?

1:24:03Sherwood Callaway:Yeah, that would be interesting. I mean, orthopedic surgery in particular is so manual. Although my dad has like an inventor streak. He's invented multiple medical devices over the course of his career, which like if you spend 40 years doing ACL repairs, like you come up with some good ideas. I'm sure that AI would have made the process of designing and developing and bringing those things to market. Yeah, yeah. 3D printers.

1:24:29Lindsay Pettingill:I mean, you know. On the subject, to continue down the family tree, I guess. So your sister works with you. which is really cool. I've met her. She's rad. She's going to HBS in a couple of months. And in the meantime, she's getting really a front row seat to building in Silicon Valley, which is cool. What is it like working with her? How does she change you? Are you intentional about, like, you know, what you want to impart to her out here?

1:24:59Sherwood Callaway:Yeah. I mean, so my sister's name is Hadley. She's five years my junior, which I think is a really good gap because five years is like you're close enough that you're friends, you empathize with each other, you have sort of shared experiences, but not so close that you compete. And Hadley, to her credit, I think has been maybe five years of professional software engineering experience under her belt at some top companies.

1:25:24Lindsay Pettingill:Was she at Brex as well?

1:25:25Sherwood Callaway:She was at Brex, but although we did not overlap, we missed each other by just a couple of months. And then she went to Doppel, which is an Andreessen-backed cybersecurity company. and more recently has been thinking about transitioning into business roles or operations roles. Wanted to sort of explore what's available to her outside of engineering and that led her to apply to business school. She's going to HBS in the fall. She'll probably still be involved with Sazabi while she does that. We'll see how long she lasts before she's... I want her to have some of that experience, but I also will be...

1:25:59Sherwood Callaway:It'll be a big loss for us. After getting into business school, she decided to come join Sazabi as their first non-technical hire, ironically, because she is an engineer. But she's been basically shadowing me and serving as chief of staff. In a lot of ways, because I'm a solo founder, I think she serves in kind of a co-founder capacity or supporting co-founder capacity.

1:26:17Lindsay Pettingill:For sure.

1:26:18Sherwood Callaway:She's there to kind of jam with me on fundraising strategy, on product questions like pricing or how to sequence our launches or manage relationships with our PR people or throw our coming out of stealth party, which was a massive success. Big hit. So she kind of fills in a lot of different gaps. I think she's honestly perfect for this role in part because she has a different personality than me. she is uh she's careful and thoughtful and uh considered and i tend to be a little bit like more bold creative and uh um like excited and i think it's there's there's a nice uh dynamic there um also i think uh obviously because she's my sister and because we have 26 years of shared history, there's a huge amount of trust there.

1:27:14Sherwood Callaway:So I can be really honest with her about challenges that I am experiencing or ways that I think her performance could be better or risks to the business. I can be completely open with her and honest with her. And I know that we both have each other's best interests at heart. And it's never, none of the feedback we share is ever critical. We're focused on making Zazabi succeed and helping each other grow. And so I don't know what to say. It's going to be a big loss. It's been amazing working with her. I've still got her for three or four months and then in a full-time capacity. And she's going to help me kind of backfill some other non-technical roles, which will, I think, take over some of the responsibilities that she's been owning.

1:28:01Sherwood Callaway:But I'm hopeful that she'll continue to own with us and maybe join us again in the spring or summer.

1:28:07Lindsay Pettingill:Out of curiosity, did you approach her? Did she approach you? Like how did that?

1:28:11Sherwood Callaway:I approached her. And this is like probably there's a pattern here where I'm often thinking about like what might be a great next move for Adley. And I want to be mindful of the fact that like that can be constructive. And I'm sure she appreciates that in some cases.

1:28:29Lindsay Pettingill:It can also probably be super annoying to like have someone who's like overbearing

1:28:33Sherwood Callaway:or cultivating you. And so I always want to give Hadley opportunities and information and choices and then to get out of her way. In this case, I told her that I thought one of the best ways for her to learn about startups and entrepreneurship and operations and how to launch something would be to come do it with me at Sazabi, which just so happened to be at an inflection point where we needed someone with her skills. What's ironic is she's been going back, she's gone back to HBS once for like a, you know, admission, admitted students, visitor day. And they're like having lectures about how to start companies, like what entrepreneurship is about.

1:29:15Sherwood Callaway:And Hadley's like, I just like raised the seed round for this thing. And like I launched the company. So I think she's really, it's funny for her to experience both sides of that. But I approached her with the idea, and there was some hesitation, I think, at first from both my parents and my sister. But everyone seems extremely happy with the outcome. Hadley has obviously performed incredibly well, and I think she's learned a lot, and she's loved San Francisco. This is her first time living here. Yeah. Yeah, it turned out to be great. That's great.

1:29:48Lindsay Pettingill:But, yeah, I don't often see it. So it's cool to meet her and hear from both sides. How did you hear about Village? Why did you choose Village? You obviously had a ton of options.

1:30:02Sherwood Callaway:So I guess when I kicked off the seed fundraise, and this video will come out when the seed is public so everyone will know the details of the raise and who was involved. We initially erased some money from J2 Ventures, which is a fund based out of Boston. They're best known for defense tech and deep tech. I had a relationship with the team at J2 through Christine Kyung, who was basically an advisor to me during my first company. Not an investor. I think she was patiently waiting for me to find the right thing to work on. And then when she heard that I was working on Sazabi, she realized this was it.

1:30:41Sherwood Callaway:I loved J2 immediately. I mean, I love Christine and Alex and John. They were very supportive from the get-go, even before I had a 40-page memo and recognized good founder market fit, I think, in a point of view, and wanted to be involved. My concern was that they were based out of Boston and that as a company that's being based in San Francisco and being in the dev tools market, it was important for me to have a reputable brand based here in San Francisco, a team on the ground in San Francisco. And so I was looking for, J2 and I really were looking for the right partner to bring in. J2's team knew the Village team because they had done some deals together and put them forward as a potential option.

1:31:28Sherwood Callaway:And I was open-minded. I had a great conversation with Ann and with Ben. But in particular, I think it was my conversation with you that sold me on it. To this day, probably one of the best pitches I've ever done. And it's the pitch is pitching itself because you're like, you get bought in and then at some point we're just jamming on ideas and riffing. And I think it meant a lot to me to have a partner who really understood my vision and knew why I was the right person to be building this company.

1:31:59Lindsay Pettingill:For sure.

1:31:59Sherwood Callaway:And it felt like you really got me. Yeah.

1:32:02Lindsay Pettingill:It was mutual. I remember the pitch. It was very easy, I think, on both sides. Because, like you said, I knew – I understood the language that you're speaking, you know, this sort of proto-thesis that I shared earlier around, you know, my language was headless BI, but –

1:32:21Sherwood Callaway:It's so funny. Often you're like, we're pitching the same ideas. Yeah. But we call them different things.

1:32:26Lindsay Pettingill:Yeah, exactly.

1:32:27Sherwood Callaway:And then we realize that that's what's happening.

1:32:29Lindsay Pettingill:Yeah.

1:32:30Sherwood Callaway:It makes the pitch super easy. Yeah, yeah. Having pitched hundreds of times now over five years, and sometimes in a sales context, sometimes in a fundraising context, you know that when someone gets it in the first five minutes, we're doing this.

1:32:47Lindsay Pettingill:Yeah, yeah, yeah, exactly. Go through the motions.

1:32:49Sherwood Callaway:That's how I felt with you. It was fun. And I got to know the rest of the Village team. Yeah. And they're obviously exceptional. They have a big portfolio of companies that we can sell into. Absolutely. in all different spaces and a very strong pedigree. And I like the village model. I think that's what we're trying to do with Angels is we're trying to bring in lots of people and create like a supporting cast of characters to help make Sazabi a success.

1:33:15Lindsay Pettingill:Well, thank you for that. We're thrilled to be working with you. And I've said this to you personally, but one of my favorite things about working with you is you have a plan and you execute on the plan, like according to schedule, Which is so hard to predict, right? Again, this comes back to, I think, the extent to which you lived and breathed this problem for years, thought really deeply about it. And then, you know, there's so many pieces that are required to build a successful startup to hit PMF. And, you know, you're on the path there. But you bring so much intention to it. You know, it's a surprise, right?

1:33:52Lindsay Pettingill:Investing is a surprise because you don't spend too much time with folks, right?

1:33:56Sherwood Callaway:You make a snap decision and then you have to spend years getting to know each other afterwards.

1:34:02Lindsay Pettingill:Yeah, and sometimes we're just gathering data points the whole time. And in spite of, I'm guessing, getting hit in the head a lot as playing lacrosse, playing ice hockey, you seem to learn quickly. You have a growth mindset, which makes it a joy to be a part of.

1:34:24Sherwood Callaway:So this is great. Lucky to have you on board.

1:34:27Lindsay Pettingill:I'm so excited to be on board. This is just the beginning, right?

1:34:33Sherwood Callaway:Hey, this is Ben Kaznoka, co-founder of Village Global. Thanks so much for tuning in to the Village Global podcast, where we go deep on all of the biggest topics in tech. If you enjoyed this conversation, please subscribe to our YouTube channel. You can check us out on Spotify, Apple, wherever you get your podcasts. We'd love to see you for the next one.