122. Timing the AI Wave with Brian Raymond | All Quiet on the Second Front Podcast
30m | Jun 23, 2026Getting AI out of the POC and into production has been the defining challenge of the last three years. Brian Raymond has lived it from the inside — building infrastructure, mistiming bets, and figuring out in real time what "enterprise-ready" actually requires.
This episode covers:
- What it takes to get AI out of the demo and into production at scale
- Why senior engineering judgment matters more than headcount in the AI era
- How Unstructured crossed the Valley of Death without forking their stack — same core code base on Game Warden and in financial services
- What a decade at CIA taught Brian about paranoia as a leadership practice
- Why the dam may have finally broken on enterprise AI adoption
Brian Raymond is CEO and co-founder of unstructured.io, an AI data infrastructure company with $65M raised, 70M open source downloads, and customers spanning financial services, defense, and enterprise SaaS.
Connect with Brian:
- LinkedIn: Brian Raymond
Connect with Tyler:
- LinkedIn: Tyler Sweatt

All Quiet on the Second Front
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