Jocko Podcast 527: From Ego to Execution, and The Path to Command. With Nate Fry
Host: Jocko Willink with Echo Charles
Guest: Nate Fry – U.S. Army Infantry Officer, Ranger, Mountain Battalion Commander, Vermont National Guard
Release Date: February 11, 2026
Episode Overview
This episode explores the journey of Nate Fry, from his rural childhood and rebellious adolescence to forging his leadership ethos through military service, personal setbacks, and mentorship. Fry shares candid reflections on ego, failure, mentorship, leadership development, and the need for realistic, skills-based military training. The discussion outlines his Army and business career, culminating in his current efforts to innovate leadership training through technology.
Key Discussion Points & Insights
1. Nate Fry’s Early Life & Formative Years
- Rural Roots & Family Background (02:00–05:00)
- Born in Alabama; moved between Alabama and Louisiana.
- Grew up in a poor, rural setting; father was a Vietnam-era Air Force loadmaster.
- Not close to younger brother initially.
- Youthful Rebellion & Redirection (05:00–08:00)
- Brief stint with the "wrong crowd," suspended for smoking.
- Saving intervention: forced into Boy Scouts (“I don’t want to join the nerd Boy Scouts...but the two Scoutmasters were super cool. They became my first mentors.” [05:08, Nate Fry]).
- Influence of Scouts: discipline, outdoor skills, running, and mentoring.
- Dual Identity: Punk Rocker & Boy Scout (06:36–09:00)
- Played bass in a garage punk band while excelling in Scouts.
- Early fascination with adventure and mountains, inspired by outdoor catalogs—road trip to Ozarks as a teenager.
2. Path to the Army: Education, Identity, and Ambition
- Seeking Escape via Education (10:00–13:00)
- Determined to leave Louisiana; guidance counselor introduces West Point.
- Earns entry to West Point despite rebellious streak (“My constitutional right to wear my hair up.” [11:00, Fry]).
- Culture shock at West Point: rigid discipline vs. his creative, punk-leaning personality.
- Pivot to ROTC for Balance (14:07–16:42)
- ROTC at Dickinson College, chosen for its Russian program.
- Experience studying in Russia, including a pivotal loss to a Russian kickboxer, leading to insight about global competition and strategy.
3. Early Military Career: Success, Frustration, and Self-Sabotage
- Commissioning and Initial Success (18:18–24:30)
- Infantry branch, Ranger school—“Ranger School wasn’t as hard as I thought because I took it so seriously and prepped for it.” [27:14, Fry].
- Key preparation advice: focus on tactics, writing notes, and attention to detail rather than just fitness.
- Reality Check as a Platoon Leader (30:09–37:11)
- Assigned to new unit; frustration at lack of challenge, ambition to be scout platoon leader unfulfilled.
- Ego and discontent lead to bad attitudes and missed deployment opportunities.
- Early lesson: “People smell when you’re mad and that always smells like it’s about you.” [34:35, Jocko].
- Ego's Downward Spiral (37:11–45:00)
- Chosen for staff roles instead of combat leadership, grows increasingly bitter.
- Attempts Special Forces (SF) selection; attitude issues continue.
- SF pipeline disrupted by personal crises (missing son’s birth) and team setbacks (recycled in Robin Sage exercise).
- Abruptly quits after being recycled: “Nobody recycles me, Fry. I don’t recycle anything...I’m too good for this.” [43:15, Fry]
- In hindsight recognizes it was a mistake fueled by pride and lack of maturity.
4. Crisis, Recovery & Mentorship
- Post-SF: Adrift and Angry (45:19–53:52)
- Shunted to an S2 (Intel) role, deployed to Afghanistan during the drawdown.
- Returns, leaves active duty after 7 years, plans to study forestry and become a mountain guide in Vermont.
- Turning Point via National Guard & Mentor (57:59–65:00)
- Joins Vermont National Guard; reconnects with purpose and service through Mountain Battalion.
- Life-altering mentorship from Lt. Col. Jason Pelletier:
“Take all the good that you ever saw and bring it here and find all the good that we have here and put it together. Just throw the bad stuff out.” [59:04, Pelletier via Fry] - Organizational culture and mentorship help tame anger and refocus energy: “I was destroying a lot of stuff. And I feel like those guys were like, I love the energy. Let’s put it in a nuclear power plant and get it to do something constructive.” [64:41, Fry]
5. Building Excellence: Mountain Warfare School & International Cooperation
- Army Mountain Warfare School (66:53–71:34)
- Describes the unique, high-caliber instructor culture and world-class training:
“It is one of the best kept secrets in the Army.” [66:58, Fry] - School’s influence on doctrine and international training efforts.
- Collaboration (and rivalry) with Marine Corps’ mountain warfare center.
- Describes the unique, high-caliber instructor culture and world-class training:
- International Duty & NATO (71:43–80:32)
- Assignments as liaison officer in North Macedonia during NATO accession and Russian invasion of Ukraine—responsible for solidifying new member into NATO.
- Strategic take on Russian military tactics and the importance of Ukraine:
“If we allow them (Russia) to win in Ukraine, it’s going to empower them to do anything they want in the Balkans as well.” [76:15, Fry]
6. Modern Military Training and the Future of Leadership
- Critical Assessment of Current Training (83:08–93:31)
- Argues military overindexes on hardware and under-invests in developing people and training skills.
- Driving concept: Leadership, decision-making under pressure, and adaptability are skills that must be trained and assessed, not just taught in books.
- Analogies to Jiu Jitsu and sports: “There are things that can only be learned by doing.” [86:40, Jocko]
- Entrepreneurial Pivot: SpireTG and Mentor Platform (107:22–110:35)
- Launching Spire TG and the Mentor platform—a simulation-based, AI-enabled environment for ROTC cadets to get constant, realistic leadership decision practice.
- “What if we had a tool that allowed us to get a data point every day on where you’re at as a leader?” [103:16, Fry]
- Not a video game, but a tool leveraging gaming engines and data analytics to tailor and track leadership growth, bridge instructor-student gaps, and provide actionable metrics.
- Currently piloted at several universities.
7. Mountain Warfare, Ski-mo, and Military Heritage
- Mountain Leadership and Physical Challenges (110:45–121:14)
- Describes the legendary Edelweiss Raid (military ski-mountaineering event in Austria):
“It’s not just about winning—it’s about functioning as a team in the mountains.” [111:09, Fry] - Army’s Mountain School basics—awarding of the coveted, once unofficial “Rams Head” patch.
- Competition and mutual respect among international mountain warfare units.
- Describes the legendary Edelweiss Raid (military ski-mountaineering event in Austria):
8. The Value of Mistakes, Humility, and Mentorship
(Closing Reflections) [126:34–127:50]
- “Mistakes are okay… You can make enough mistakes at a certain point, you actually bludgeon your way through and realize I can reform and change and recover. And really, it comes down to mentorship… More people investing in other people. All the hardware in the world—we need it—but we need to build the complexity of the American leadership mind.” — Nate Fry, [126:34–127:50]
Notable Quotes & Memorable Moments
"I was the honor graduate from my ROTC class, the honor grad from IOBC, did the Colonel Puckett board in Ranger School... Thought I was hot stuff. But I wasn’t the only one that was good. When you go into this thinking you’re honorary, you better bow down before me...dude, you’re a second lieutenant. Chill out."
— Nate Fry, [37:11]
"The world did not revolve around you. But it took me another eight years to figure that out."
— Nate Fry, [34:03]
"People smell when you’re mad, and people smell when you’re frustrated. That always smells like it’s about you.”
— Jocko Willink, [34:35]
"I was destroying a lot of stuff. And I feel like those guys were like, I love the energy. Let’s put it in a nuclear power plant and get it to do something constructive."
— Nate Fry, [64:41]
"Leadership is the most important thing on the battlefield, and there’s no doubt about it."
— Jocko Willink, [127:50]
"You have to get up every day and get after it."
— Jocko Willink, [139:03]
Important Segments & Timestamps
- Nate’s rural childhood & Boy Scouts: 02:00–08:00
- Punk band & mountains: 06:36–09:00
- Escaping Louisiana—West Point & ROTC: 10:00–16:42
- Russian cultural & kickboxing lesson: 19:00–23:00
- Ranger School & leadership advice: 24:30–30:06
- Career frustrations, missed opportunities: 30:09–45:00
- Mentorship & correction in Vermont Guard: 57:59–65:00
- Mountain Warfare School & international missions: 66:53–80:32
- Strategic assessment of Russian threat: 76:15–80:32
- Building SpireTG & Mentor platform: 107:22–110:35
- Edelweiss Raid, Ski-mountaineering: 110:45–121:14
- Reflections: humility, facing mistakes: 126:34–127:50
Summary & Takeaways
- Resilience From Mistakes: Fry’s journey is one of recurring setbacks driven by ego, eventually remedied by mentors who show him the value of humility, resilience, and focusing on the team over self.
- Mentorship Is Critical: Transformative leadership happens when senior leaders harness, rather than crush, junior leaders’ energy, and redirect it toward mission and growth.
- Train the Mind, Not Just the Trigger Finger: Real combat and organizational effectiveness come from decision-making and adaptability under pressure—skills that require iterative, contextual training, not just lectures or static simulators.
- The Future of Leadership: Fry’s Mentor platform aims to fill the military’s “people-skills” training deficit with scalable, data-driven, simulation-based decision-making reps, enabling persistent, measurable growth.
- Embrace the Team, Embrace the Work: Even standout talents must serve the team and seize every assignment with full effort—attitude and humility go further than credentials.
Connect with Nate Fry & the Mountain Battalion
Whether in combat or business, leadership is not about ego, but about learning, adapting, and investing in the people beside you—every day, on every mission.