The Shawn Ryan Show – Episode #257

Guest: Jocko Willink – Commander of SEAL Team-3 Task Unit Bruiser

Release Date: November 27, 2025
Host: Shawn Ryan
Length: ~6 hours

Episode Overview

This Thanksgiving episode brings together two former Navy SEALs, Shawn Ryan and Jocko Willink, for a deeply candid and powerful interview. Jocko discusses his journey from rebellious small-town kid to leader of the most decorated special operations unit in the Iraq War, Task Unit Bruiser. They reflect on SEAL experiences, leadership lessons, profound loss, brotherhood, and Jocko’s transition into business and personal development after his military career. The episode is rich with actionable leadership insight, stories of heroism and tragedy, and emphasis on humility, ownership, and service.

Main Themes

• Leadership and Extreme Ownership: Hard-learned lessons about responsibility, humility, empowering others, and accountability under fire.
• Brotherhood and Sacrifice: The tight-knit bonds of SEAL teams; stories of loss, trauma, and honoring teammates.
• Adaptation and Professionalism: Navigating peacetime SEAL life vs. wartime, and the constant effort to prepare and improve.
• Post-Military Purpose: Jocko’s pivot to business, writing, youth mentorship, and patriotism.

Part 1: Early Life and Military Motivation

[10:35]

• Grew up in a small New England town, middle child, both parents were schoolteachers.
• Not a standout athlete; gravitated to heavy metal and hardcore music—a DIY ethic that influenced his life.
• Describes a rebellious streak driven by the usual teenage angst, energy, and need to break the mold.

"I've always been a little bit of a rebellious kid, and so that kind of made me feel like I was scratching that itch." – Jocko [12:00]

[14:08]

• Obsessed with the military even as a child, collecting action figures and dreaming of being a commando.
• Eventually realized he could do this as a “real” job; naturally drawn to the SEAL Teams.

[17:26]

• Raised Christian, family-oriented values from going to church in youth.

Part 2: Joining the SEAL Teams & Early Career

[21:42]

• Enlisted in 1990 at 18; the Gulf War had just begun.
• Excitement at boot camp; no SEAL mentors prior to arrival at BUD/S.
• Bud/s was tough but approached every failure as opportunity to work harder.

"I overcame failure just by pure, just aggressive hard work." – Jocko [27:52]

• Emphasizes the importance of not quitting:

"Don’t quit. Statistically, that’s how you make it—just don’t quit." – Jocko [31:19]

[31:26]

• Arrival at SEAL Team 1 was intimidating and disciplined; “no fun one” culture.
• Not much combat experience in the peacetime teams, aside from some Vietnam vets.

"As much as the Vietnam guys passed down as much as they could, but it still was like you didn't really know what it was you were training for." – Jocko [37:36]

Part 3: First Leadership Lessons & Life-Altering Losses

[50:32]

• Early in his officer journey, friend and platoon leader Alton Lee Grizzard was killed in a tragic murder-suicide. Led to a first, powerful lesson in perception versus intent and the essential nature of self-awareness as a leader.

"The way you perceive yourself is not going to be accurate all the time ... there's a really good chance their perception is more accurate than your own." – Jocko [55:09]

• Mutiny in his platoon—got a problematic officer fired, replaced by a legendary, humble leader; this contrast became Jocko’s template for leadership.

"He just put that responsibility and gave us ownership. That guy left me with a lot of lessons." – Jocko [61:09]

Part 4: Leadership Philosophy – Caring Beyond the Job

[7:43] (Patreon Q&A)

• Biggest regret as a leader: Not taking more interest in his men’s lives outside the teams—finance, education, life after service.

"I never really cared about what happened after the teams. For me, it was always about the teams." – Jocko [7:43]

"If a guy was having problems with his marriage or kids I would do whatever I could to help him—so he could get back to being in a platoon." – Jocko [9:36]

Part 5: Transition to Officer & Learning Both Sides

[84:49]

• Chose to become an officer to follow in the footsteps of a leader who made life in a platoon “awesome.”
• Experiences as an enlisted and then officer gave him “bilingual” ability—fluency in both E-5 mafia and officer language—helping translate realities up and down the chain of command.
• Emphasis on keeping subordinates informed, context, and explanation.

"If you fail to do that, they'll have no idea, and you won't know that they don't know, and that's a disaster." – Jocko [96:01]

Part 6: Early Combat Deployments and Principles of Ownership

[108:44]

• First combat in Iraq in Baghdad, 2003—platoon deeply integrated in high-tempo direct action missions.
• Early lessons in being in charge, managing risk, and building trust:

"You know why these guys listened to me? Because I listened to them. You know why these guys treated me with respect? Because I treated them with respect." – Jocko [116:27]

Part 7: Task Unit Bruiser – Ramadi

[149:57]

• Chosen as Task Unit Commander, led Task Unit Bruiser—a legendary group (Chris Kyle, Marc Lee, Michael Monsoor, Leif Babin, Seth Stone, et al).
• Renamed unit “Bruiser” for morale and team identity, inspired by Colonel David Hackworth.

"You’re not just Team Alpha or Team Bravo. You’re Task Unit Bruiser. Let’s go." – Jocko [153:19]

• Emphasis on real danger: "I was just enough ahead of the power curve to know what was coming. And I told the task unit on the ground: this is going to be a historic deployment." [161:40]

Part 8: Tragedy, Ownership, and Heroism in Combat

[187:32]

• Detailed account of the first major blue-on-blue (friendly fire) incident in Ramadi.
• Heartbreaking story of how he personally processed the incident, and the moment he realized he must shoulder all responsibility as the leader:

"When you are in charge of a team and something goes wrong, it is your fault." – Jocko [204:33]

• Built immense respect and credibility with the team by owning the failure and immediately implementing lessons to prevent future blue-on-blues.
• Examples of other blue-on-blue near-misses and the need for constant vigilance, communication, and humility.

"The guys in the troop, the guys in the task unit...I think I did what they probably expected I was going to do." – Jocko [207:32]

• Open, raw stories of catastrophic loss:
  • Cowie: severely wounded, begged to stay with his brothers.
  • Ryan Job: shot in the face, later died from complications.
  • Marc Lee and Michael Monsoor: killed on deployment, left lasting legacies.

"Mark was the first SEAL killed in Iraq...It's a heavy weight, we've got to hold the line." – Jocko [170:24]

"[After a loss] I told my guys the truth...I don't know what to tell you, all I know is what I know how to do, and that's work. We're going to go back to work, and we're going to take the fight to these moosh, and we're gonna kill as many as we can." – Jocko [254:23]

Part 9: The Burden of Command and Lessons Translated

[255:54]

• Navigated the aftermath of loss by focusing on work and supporting his team emotionally.
• Leadership requires knowing when to have your men’s back, and also setting clear moral/ethical boundaries.
• Jocko awarded Silver Star for actions during this deployment, but emphasizes—again—that credit goes to the whole team and army/marine partners.

Part 10: Post-Combat, Teaching, and New Mission

[291:59]

• Returned home, assigned himself to SEAL training command (TRADET) to better prepare the next generation for real war.
• Decision to leave after 20 years, focusing on family and recognizing that “if you can't give the teams everything, it's not the best thing.”

"You know, I was married to the teams, and my wife and family came second." – Jocko [300:49]

• Opened a Jiu Jitsu gym, accidentally became a business and podcasting leader, and realized universal applicability of his leadership lessons.
• Emphasis on ownership—personally and in business.

Part 11: Building Legacy – Books, Businesses, and Giving Back

• Jocko’s companies: Echelon Front (leadership consulting), Origin USA and Jocko Fuel (American manufacturing and nutrition), children's books (Way of the Warrior Kid series and "Mikey and the Dragons").
• Upcoming Way of the Warrior Kid movie starring Chris Pratt as Uncle Jake (Jocko has a cameo).
• Purpose-driven entrepreneurship: “If we don't have the ability to make things and be self-sufficient, we will lose.” – Jocko [327:46]

Part 12: Reflections, Patriotism, and Advice

On America’s Divisions:

• Social media algorithms amplify division and anger, but real America, in person, is largely united by desire for strong families, honest work, and optimism.

"Open your eyes, open your ears, listen more, try and understand other people's perspectives, try and figure out where you can agree with them." – Jocko [333:28]

On Leaving the Teams:

• Still battles with the decision: “The teams gave me everything.” [301:08]

On Generational Advice:

• America offers opportunity, but you gotta work for it. Choose your game wisely. Seek “lore”—that is, the stories and struggle that build meaning in your life.

"Enjoy it. When you go through challenges, look at it as an opportunity to make some lore for your existence." – Jocko [344:13]

On Service and Sacrifice:

• Reinforces the sacrifices of conventional forces—soldiers and marines—as deserving of the highest respect.

"There was so much heroism in that city...so many stories—I'm giving you a little fraction of my view." – Jocko [265:12]

On Healing and Grieving:

• "You get sad when you think about your friends—it's okay. You get a tear in your eye when you hear the national anthem—it's alright, man." – Jocko [352:37]

Notable Quotes and Emotional Moments

• [204:33] “When you are in charge of a team and something goes wrong, it is your fault.” (Jocko)
• [164:13] “If you're more concerned about yourself than your platoon, you will not work for me.” (Jocko)
• [254:23] “I don't know what to tell you...all I know is what I know how to do, and that's work.”
• [255:54] "Would I have changed anything? Maybe. But I don't know that there's anything else to do in a situation like that." (Jocko)
• [300:49] "I was married to the teams, and my wife and family came second."
• [337:15] “Almost all people, if you say, you got family, you want your kids to have a nice place to live—they’ll say yes. At least we have that common ground.”
• [344:13] "When you go through challenges, you face things in life, look at [them] as an opportunity to make some lore for your existence."

Key Timestamps

• Leadership reflection & advice: [7:43], [50:32], [61:09], [84:49], [96:01]
• Ramadi deployment: setup & loss: [160:43], [187:32], [254:23]
• Blue-on-Blue Incident/Owning Mistakes: [203:30], [204:33]
• Lessons from leaving service: [291:59], [301:08]
• Building Origin/Jocko Fuel: [326:06], [329:13]
• Way of the Warrior Kid Movie Announcement: [316:30]
• Modern America/Generational advice: [333:28], [344:13]

Summary

Jocko Willink’s appearance on The Shawn Ryan Show is a lesson in humility, deep responsibility, and service. He opens up about loss, leadership, and hard choices with rare candor—never shying from mistakes, but always seeking to learn and grow.

This episode is an immersive look into what makes a true leader and warrior, equal parts tribute to fallen brothers, practical leadership seminar, and a call for personal accountability and unity amid division.

For anyone interested in real insight into military leadership, the bonds of the SEALs, and living a life of honor and extreme ownership, this is essential listening.

Recommended Next Guests:

• JP Donnell
• Debbie Lee
• Johnny Clark (Vietnam grunt, author of "Guns Up")