Guerrilla Intelligence: Bob Gourley on the Real OODA Loop, AI, and Winning the Information War

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Bob Gourley spent 14 years in operational intelligence — tracking Soviet naval movements, supporting ships and submarines in some of the most dynamic environments on earth — before he ever heard the name John Boyd. His regret: nobody told him sooner.

Gourley is the founder of OODA LLC, co-host of OODAcast, and one of the sharpest observers of the intersection where cybersecurity, geopolitical risk, artificial intelligence, and decision making under uncertainty collide. He runs OODAcon — an annual event he describes as less about OODA and more about orientation: what do you need to know to survive the next 12 months?

In this conversation with Brian “Ponch” Rivera and Mark “Moose” McGrath, Gourley draws a direct line from the intelligence cycle — collect, process, analyze, disseminate — to the same linearization error that has plagued every corporate OODA training in every hotel ballroom in America. The cycle fails for the same reason the four-step loop fails: because the adversary is moving while you’re still in phase two.

The conversation ranges from consciousness and psychedelics to AI’s destruction and creation moment across the technology sector. Gourley names what most executives are missing: supply chains built on helium, chips built on radioactive decay, and bond markets that cannot be managed into submission.

He also issues a direct challenge to anyone teaching the OODA loop as a sales process: they are going to suffer in life.

John R. Boyd's Conceptual Spiral was originally titled No Way Out. In his own words: 

“There is no way out unless we can eliminate the features just cited. Since we don’t know how to do this, we must continue the whirl of reorientation…”

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