Shawn Ryan: I Watched Tier 1 Operators Get Destroyed in CIA Tryout

About this video

Ritland recounts his guest’s experiences working as a CIA contractor following special operations service. The guest describes the month-long tryout process with its difficult shooting and fitness qualifications, high attrition rates, and the multi-unit culture. He then shares stories from rotations in Afghanistan and anti-piracy work, including defensive engagements, a 12-hour ordeal after being compromised at a safe house, and the undercover nature of the work.

Key takeaways

• Ritland’s guest recounts that the CIA contractor tryout involved rigorous shooting qualifications (especially at 25 yards from concealed carry) and physical tests, with only about 3 out of 15 candidates passing in his class.
• The guest describes anti-piracy contracting work as mostly monotonous shipboard duty interrupted by brief, intense encounters with armed Somali skiffs, some involving coordinated ambush tactics.
• According to the guest, CIA mobile security work often involved extended undercover operations with small teams in high-risk environments, where engagements were typically quick and defensive in nature, with the goal of avoiding detection rather than seeking contact.

Episode details: published June 10, 2026 · 349.5K views · 29:06 long. Summary written by Self Growth Videos from the episode itself. Stories told by Mike Ritland’s podcast guests are the guests’ own accounts, attributed to them — not independently verified. Commentary is Ritland’s, presented as his analysis.

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