About this episode

Sherwood Callaway discusses his unconventional path in engineering and the philosophy behind Sazabi's approach to observability.

Sherwood Callaway is the founder and CEO of Sazabi, an AI-native observability platform, and a repeat YC founder. He previously worked as an early infrastructure engineer at Brex, where he built the systems that kept one of the fastest-growing fintechs in the world running. Village Global Luminary LP Lindsay Pettingill sits down with Sherwood for a conversation that moves from his unconventional path into engineering to the contrarian bets behind Sazabi. They dig into why Sherwood believes logs alone can replace metrics and traces, why dashboards mostly serve anxiety rather than insight, and what a world of self-healing software could actually look like. Along the way, Sherwood reflects on the 40-page manifesto that became Sazabi's founding thesis, the angel investor strategy that brought over 100 founders and technical leaders onto his cap table, and the maximalist, Blade Runner-inspired brand built around a name pulled from a 1980s anime. The episode closes on a more personal note, touching on his orthopedic surgeon father's late-career turn toward vibe coding and his sister Hadley's stint at Sazabi as its first non-technical hire before business school. Thanks for listening…

People in this episode

Host: Lindsay Pettingill

Guest: Sherwood Callaway

Topics covered

• AI-native observability
• engineering
• self-healing software
• metrics vs logs
• founder journey
• investor strategy

Keywords

• observability
• metrics
• logs
• self-healing software
• founders
• investing
• technology

Mentioned in this episode

Organizations: Sazabi, Brex

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