START pod: Sherwood Callaway, Founder & CEO, Sazabi “Observability On Autopilot”

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Option 1 (The Two Halves)

Sherwood was using Cursor and Claude Code to build an AI agent. Futuristic tools, futuristic product. Then a production bug fired and he was clicking through Datadog dashboards that looked exactly like 2015.

Option 2 (The Non-Linear Path)

History major. Mining Bitcoin from his dorm room. Turned down an investment banking internship to do a coding bootcamp where people sat on cushions and did yoga. Now he's building the next Datadog.

Option 3 (The Accidental YC Return)

YC's engineering team emailed Sherwood about a job. He said, "Actually I'm building something new." Within minutes they forwarded his email to Aaron Epstein. He didn't even get the double opt-in.

Option 4 (The Dalton Moment)

Dalton Caldwell told Sherwood, "I don't believe you really want to start this company. You're still at Brex." Sherwood said, "I'm begging you. I'll quit today." He quit that day.

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Sherwood was using Cursor and Claude Code to build an AI agent. Futuristic tools, futuristic product. Then a production bug fired and he was clicking through Datadog dashboards that looked exactly like 2015.

The first half of software development got automated. The second half didn't. That contrast felt so obvious to him he thought about it obsessively for two weeks before deciding to quit and build Sazabi.

His path to this moment is one of the most non-linear I've heard. History major at Davidson College. Mining Bitcoin from his dorm room. Turned down an investment banking internship to do Dev Bootcamp batch zero in 2014 where people sat on cushions and did yoga. Got a job at Crunchbase. Then employee 70 at Brex, where he built the observability team and watched the company go from $1B to $12B. Then started a medical billing company through YC. Then built an AI SDR at Eleven-X that grew past $10M ARR.

The first time he did YC, Dalton Caldwell told him "I don't believe you really want to do this. You're still at Brex." Sherwood said, "I'm begging you. I'll quit today." Quit that day.

The second time, YC's recruiting team emailed him about a job. He said he was building something new. They forwarded his email to Aaron Epstein. He didn't even get the double opt-in.

Now he's building the next-generation observability platform for teams of 5 to 50 engineers shipping in the age of AI. His thesis: "Code is basically free. System design, architecture, and reliability are the new bottlenecks."

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🎙️ Sherwood Callaway, Founder & CEO, Sazabi on Fondo START pod

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01:08 Building AI-native observability for fast-moving engineering teams

02:07 "Code is basically free"

02:36 Why architecture and product thinking are the new bottlenecks

07:10 Building Brex's observability team from employee 70

09:00 History major to Dev Bootcamp batch zero to Brex

11:30 "I'm begging you. I'll quit today." The Dalton Caldwell moment

13:33 The Cursor vs. Datadog contrast that inspired Sazabi

15:10 "We'll automate the second half of the software lifecycle"

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Check out www.sazabi.com