Jocko Willink (@jockowillink) is one of the scariest human beings imaginable. Jocko did his first interview with tim and it took the Internet by storm. Now he is back for round two to answer the questions you’ve been asking.
Jocko is a lean 230 pounds. He is a Brazilian jiu-jitsu expert who used to tap out 20 Navy SEALs per workout. He is a legend in the Special Operations world. His eyes look through you more than at you.
Jocko spent 20 years in the US Navy and commanded SEAL Team 3’s task unit Bruiser, the most highly decorated special operations unit in the Iraq War. Upon returning to the US, Jocko served as the officer in charge of training for all West Coast SEAL teams, designing and implementing some of the most challenging and realistic — and perhaps psychotic — combat training in the world (his words, not mine).
After retiring from the Navy, he co-founded Echelon Front, a leadership and management consulting company and authored the number one New York Times bestseller Extreme Ownership: How US Navy SEALs Lead and Win.
Ryan Holiday (@RyanHoliday) is a strategist and writer. He dropped out of college at 19 to apprentice under Robert Greene, author of The 48 Laws of Power, and later served as the director of marketing for American Apparel. His company, Brass Check, has advised clients like Google, TASER, and Complex, as well as many prominent bestselling authors. Holiday has written four previous books, including The Obstacle Is the Way, which has been translated into 17 languages and has a cult following among NFL coaches, world-class athletes, TV personalities, political leaders, and others around the world. Ryan lives on a small ranch outside of Austin, Texas, and his latest book is Ego Is The Enemy.
Ryan and Tim cover a lot in this conversation, including:
Meltdowns and how Ryan handles them
Workaholics Anonymous — How it works, what worked for him, what didn’t
The tipping points for his last book, The Obstacle Is the Way
External versus internal obstacles
Sherman versus Grant leadership and “success”
Howard Hughes versus Elon Musk
Thinking of “first principles”
If you only have 5 minutes, listen to what Ryan believes is one of the biggest threats to your creativity.