Shawn Ryan on Contracting and Anti-Piracy Work After the SEAL Teams

In a sit-down interview on Mike Ritland's channel, Shawn Ryan opens up about life after the SEAL Teams, walking through his time as a private military contractor and the strange, small-world moments that came with it. The conversation ranges from high-level mobile security work overseas to a stretch doing anti-piracy operations off the Horn of Africa, with Ryan offering candid, unfiltered detail on what that work actually looked like day to day.

Key points

• Contract work surprised the client: Ryan describes teams of mostly special operations veterans being underused at first, until leaders realized the capability they had and started assigning more unconventional missions.
• A battlefield reunion: Ryan recounts running into a former captain, Rick Smothers, by chance in Afghanistan, watching a firefight from a rooftop while catching up on why they both left the Teams.
• Anti-piracy duty near Somalia: Ryan calls the job "like a video game," mostly boredom broken by brief, intense encounters with pirate skiffs armed with AKs and RPGs.
• Close calls at sea: He describes a tense standoff involving over a dozen skiffs that turned out to be a probe, and other engagements that ended almost as soon as they started.
• Why he left: Ryan tells Ritland the decision came down to frustration with politics limiting the work he wanted to do.

Quick take

This is less a tactical breakdown and more a personal, war-stories conversation, but it gives useful context on how contracting work actually unfolds after someone leaves the Teams. Worth a watch for the firsthand detail Ritland pulls out of Ryan.

Watch the full video: Mike Ritland