SHOW / EPISODE

122. Timing the AI Wave with Brian Raymond | All Quiet on the Second Front Podcast

30m | Jun 23, 2026

Getting 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.


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