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

**Sherwood Callaway** (0:00)
Sazabi's mission is to be the default observability solution for companies of all sizes during the AI era. And our vision is a world where software heals and improves itself without human intervention or direction. 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. I'm a big believer in like creating, I mean, here we are at Village Global, so we're creating a village.
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.

**Lindsay Pettingill** (0:43)
Welcome to the Village Global Podcast. I'm Lindsay Pettingill, investment partner at Village Global. My guest today is Sherwood Callaway, founder and CEO of Sazabi. Sherwood is a repeat YC founder and early engineer at Brex, where he built the infrastructure and observability systems that kept one of the fastest growing fintechs in the world running. He knows what it looks like when complex systems break at scale.
Today, we're gonna talk about what AI coding tools are actually doing in the software development life cycle. Not the hype version, but the messy reality of what happens when code gets generated faster than anyone can track it in production. We'll get into Sherwood's contrarian take on observability and what self-healing software actually means in practice. This is a conversation for people who build software or invest in the people who do. Sherwood, welcome to the show. Hey, look at that. Here we go.
I'm so excited.

**Sherwood Callaway** (1:40)
Likewise.

**Lindsay Pettingill** (1:41)
We're going to go over hills and valleys, everything in between. Would love to start off with you just talking about who you are, where you're from. We spend so much time talking about where we are today, but I think so much of that is informed by where we've come from.
You can take this in so many directions, but I'm really curious to hear 10-year-old Sherwood, what would he say about where we are today?

**Sherwood Callaway** (2:10)
Gosh, yeah, I'm not sure. 10-year-old Sherwood is pretty judgmental, I think. I think he had a high bar for what a well-lived life looks like.
I think what I was probably most interested in at 10 was guitar and rock music or computers and online games. I was decidedly not interested in any of the things that my parents did. My dad was a doctor. I was a little rebellious and I think-

**Lindsay Pettingill** (2:40)
What did that look like?

**Sherwood Callaway** (2:42)
It just meant frequently being in the principal's office, usually for innocuous things.
It meant getting on my parents' nerves quite a bit. I think that I grew up in North Carolina and was basically a punk in preppy upper middle class North Carolina and really did not resonate with the culture there. And so I think for a long time, I felt like an outsider or I wasn't where I belonged. I remember being ambitious for a long time, like wanting to do something great or to have an impact. But at some point, that was like starting a great band or being a musician.

**Lindsay Pettingill** (3:28)
Well, who were the influences as, what kind of music were you listening to?

**Sherwood Callaway** (3:32)
I've always loved like hard rock, metal, punk rock, post hardcore.
I mean, just this morning, I was listening to like early Fall Out Boy, early Green Day. Shout out to Green Day Bay Area band.

**Lindsay Pettingill** (3:44)
Yeah.

**Sherwood Callaway** (3:45)
Like I think in some sense, my musical taste is regressed. That's how I got in order.

**Lindsay Pettingill** (3:50)
We seek comfort when we're founding something.

**Sherwood Callaway** (3:52)
Exactly.
I don't have a lot of time to discover right now. So I reach for old and familiar music. But I mean, when you start your day with a hard rock, Green Day song, every day, I think it probably says something about who you are.

**Lindsay Pettingill** (4:06)
You're showing up. Yeah.
So you also played sports, right? So I guess I'm curious about, did that counterbalance the feelings of not fitting in? Was it orthogonal to all of that? Because sports are such a part of Southern culture, right?

**Sherwood Callaway** (4:26)
Though I guess maybe you played non-modal sports. I mean, I played ice hockey, which maybe is actually archetypally not a fit for growing up in North Carolina.

**Lindsay Pettingill** (4:36)
Yeah.

**Sherwood Callaway** (4:37)
I always grew up playing contact sports. My dad's from Tennessee and my mom's from North Carolina, so they aren't exactly the type to be concerned about.