The End of Manual Debugging

In this episode of Founder Firesides, YC General Partner Aaron Epstein talks to Sherwood Callaway, founder of Sazabi (P26), who exited his first YC company and is coming back through YC for a second time. Sazabi is an AI-native observability platform that replaces tools like Datadog, letting engineers ask plain-English questions about their production systems instead of digging through dashboards. They discuss why logs are the only telemetry you need, lessons from building a company that didn't play to his strengths, and why maintaining software is AI's biggest untapped opportunity. Apply to Y Combinator: https://www.ycombinator.com/apply Work at a startup: https://www.ycombinator.com/jobs Chapters: 00:00 — Back to YC for a second time 00:24 — The AI tool fixing production bugs 01:36 — “Logs are all you need?” 03:43 — Inside observability at Brex 07:42 — Starting a healthcare startup 12:21 — When the first startup unraveled 17:02 — The insight behind Sazabi 22:51 — Returning to YC 27:00 — Lessons for founders + hiring

Aaron EpsteinhostSherwood Callawayguest

Mar 27, 202629mWatch on YouTube ↗

EPISODE INFO

Released: March 27, 2026
Duration: 29m
Channel: YC Root Access
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

In this episode of Founder Firesides, YC General Partner Aaron Epstein talks to Sherwood Callaway, founder of Sazabi (P26), who exited his first YC company and is coming back through YC for a second time. Sazabi is an AI-native observability platform that replaces tools like Datadog, letting engineers ask plain-English questions about their production systems instead of digging through dashboards. They discuss why logs are the only telemetry you need, lessons from building a company that didn't play to his strengths, and why maintaining software is AI's biggest untapped opportunity. Apply to Y Combinator: https://www.ycombinator.com/apply Work at a startup: https://www.ycombinator.com/jobs Chapters: 00:00 — Back to YC for a second time 00:24 — The AI tool fixing production bugs 01:36 — “Logs are all you need?” 03:43 — Inside observability at Brex 07:42 — Starting a healthcare startup 12:21 — When the first startup unraveled 17:02 — The insight behind Sazabi 22:51 — Returning to YC 27:00 — Lessons for founders + hiring

SPEAKERS

Aaron Epstein
host
Host of YC Root Access.
Sherwood Callaway
guest
Founder of Sazabi (AI-native observability) and previously founded Opkit (YC S21); former infrastructure/observability engineer at Brex.

EPISODE SUMMARY

In this episode of YC Root Access, featuring Aaron Epstein and Sherwood Callaway, The End of Manual Debugging explores sazabi bets AI-native observability makes manual debugging largely obsolete forever Sazabi positions itself as an AI-native successor to Datadog/Sentry, letting engineers ask natural-language questions to quickly identify root causes, affected customers, and responsible commits during production incidents.

RELATED EPISODES