From US Army Intelligence to Private Sector Intelligence Advisor - Interview with Jeremy Levin (S02E05)

In this interview, Jeremy Levin shares his journey into US Army intelligence and subsequent move into private sector intelligence. Jeremy has extensive experience in intelligence analysis, training, and management, emphasizing the importance of adaptable skills, continuous learning, and effective team utilization in the field.

Jeremy Levin accidentally entered military intelligence in the mid-90s by joining the U.S. Army intelligence. He served nearly 30 years in various government intelligence roles and as a contractor. After moving into the private sector he founded Questimation (“Better decisions discovered”) to teach thinking, analytic methods, and explore more objective calibration of qualitative probabilities.

This in-depth interview explores the challenges and opportunities in intelligence analysis, focusing on metrics, training, AI integration, and the mindset needed for future success. Discover how to measure impact, foster analyst development, and adapt to technological advances.

Resources and references mentioned

Questimation - https://www.questimation.com/

Julia Galef - The Scout Mindset - https://www.amazon.com/Scout-Mindset-Perils-Defensive-Thinking/dp/0735217556

IARPA Reason Project for AI in Analysis - https://www.iarpa.gov/research-programs/reason

US Intelligence Standards ICD 203 - https://www.dni.gov/files/documents/ICD/ICD-203.pdf

UK Intelligence Standards - https://www.gov.uk/government/publications/phia-common-analytical-standards/phia-common-analytical-standards

New Zealand Code of Ethics - https://nziip.org.nz/code-of-ethics/

Chapters

00:00 Meet Jeremy Levin

07:52 Contractor Life and 9/11

22:43 Going Independent and forming Questimation

30:30 What Counts as Intelligence

35:22 Analyst Tasks and Management

41:53 Value of Warning and Training

57:51 Metrics Drive Output

01:02:20 Measuring Intelligence Value

01:12:00 Defining Success Metrics

01:22:18 Analytic Standards Matter

01:25:48 AI and Tradecraft Future

01:48:10 Mentors and Closing

This conversation is a compressed edit of an interview Freddy has conducted as part of his PhD research. The interview happened on July 2nd, 2025 in London, UK.

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