The Captain + Jess
Captain Cunningham + Jess
Brian is a former Navy SEAL and technology strategist. Jess interrupts his work to ask honest, sometimes ridiculous questions about topics from leadership to his time in the military.
The Captain + Jess
Brian is a former Navy SEAL and technology strategist. Jess interrupts his work to ask honest, sometimes ridiculous questions about topics from leadership to his time in the military.
About us
Brian is a former Navy SEAL and technology strategist. Jess interrupts his work to ask honest, sometimes ridiculous questions about topics from leadership to his time in the military.
Capt. Brian G. Cunningham
USN (Ret.) · Technology Strategist · Speaker
Two careers in environments where the cost of a wrong call is paid in real consequences. Speaks, writes, and advises on leadership, decision-making, and the future of conflict.
Jess Cunningham
The one with the questions
The honest, sometimes ridiculous ones. The ones nobody else gets to ask the Captain. The reason any of this actually gets said out loud.
The Captain's Reading List · Free
I get asked the same question in every boardroom and at every speaking engagement: what should I be reading? This is the actual list — the books I've returned to across two careers in Naval Special Warfare and the technology executive world. Each one earned its spot.
Get the list
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The list is on its way. If you don't see it in a couple of minutes, check your promotions tab — or just open it now.
Open the list now →Partnerships
The brands, gear, and places that have earned a spot in our day-to-day. Each one is a partnership we stand behind — and a link you can use to get the same thing.
Interested in partnering with us?
Reach out here →Connect
The places we share what we're reading, what we're building, and what we're learning along the way. Pick your platform.
“The list is his. The questions are mine. The next chapter is ours — and you're early.” — Jess