Cleared Hot – Episode 404

Guest: Matt Graham
Title: Air Marshals, the CIA, and the World's Best Mission Timers
Date: August 25, 2025
Host: Andy Stumpf

Overview

In this episode, Andy Stumpf welcomes Matt Graham—a military veteran, former air marshal, CIA contractor, and founder of Ares Watches—for a riveting, in-depth discussion. Together, they explore Matt's unconventional career path from law enforcement to federal service and covert agencies, the evolution of “foundership” and belief in leadership, the realities of government operations, and Matt’s journey creating the world’s premier operational watches. Throughout, the duo unpacks leadership lessons, tales from federal work, and the heart of American small-business manufacturing.

Key Discussion Points

The Unusual Paths to Success and Entrepreneurship

(00:45–11:30)

• Starting Out: Matt Graham describes his upbringing surrounded by civil servants—firefighters, cops, teachers—and his early aspirations to become a firefighter, then police officer.
• Air Marshal Genesis: After 9/11, opportunity and curiosity led Matt into the Air Marshal Service, inspired by the tactical challenges of boarding and securing aircraft.
• Federal Service Realities: The application processes for both Air Marshals and the CIA involved chance, networking, and the willingness to move and adapt.

“Normally… how I went from small town law enforcement to the CIA, the answer is a series of poor life decisions. But as is the case often.”
—Matt Graham (32:59)

The Nature of Foundership and Leadership

(10:34–23:00)

• Defining Foundership: Matt introduces “foundership” as a first-principles discipline—the ability of the founder to carry belief through growth, time, and context, separate from traditional leadership models.
• Military vs. Civilian Models: Andy and Matt discuss how military leadership’s buy-in and sacrifice rarely maps to civilian workplaces. Civilian employees need belief, not just orders.
• Struggling with School: Matt explains going back to school (MBA program) to learn the “foreign language” of business and provide tools for his family business.

“How come I’m getting these poor grades when it comes around leadership in business?...These aren't leadership issues. They're foundership issues.”
—Matt Graham (16:24)

Learning, Language, and Becoming “Fluent” in New Arenas

(06:13–11:10, 35:00–41:00)

• The Importance of Business Fluency: Matt likens learning finance to learning a foreign language: essential in the new world of business and entrepreneurship.
• Transferring Knowledge: Discusses whether a founder, by learning and teaching, unintentionally robs the next generation of their own hard-won experience.

“If I’m going to build this and steward this, then I should have those things to be able to translate that and push that forward.”
—Matt Graham (08:09)

The Realities and Ironies of Air Marshal & Agency Operations

(34:55–56:00)

• Living the Job: Matt chronicles daily air marshal life: endless flying, intensive shooting quals, and a pay-for-performance system (“shoot for pay”) with unlimited ammo.
• Operational Tactics: Stories from the field—hijack training, weapons qualifications, and high standards.
• Transition to the Agency: Through an unlikely series of connections, Matt moves from Air Marshals to a CIA training role, recounting hiring processes and personal struggles during family emergencies.

“As a guy that came from a shooting background...they reward me based on my ability to run a gun? Like, who’s doing that?”
—Matt Graham (43:44)

The Culture of Elite Organizations—From Inside and Out

(13:54–16:50, 61:45–68:30)

• Selection and Peer Groups: High standards, the necessity to “earn the seat at the table,” and the value of learning from seasoned operators.
• Operational Simplicity: Even the top agencies rely on practical, sometimes low-tech, solutions—like “mission timers” marked on hands with Sharpies, not high-tech gadgetry.

“People will be disappointed to hear that at the agency, highly capable individuals [were] writing on their hand with a Sharpie... They would want it to be some high-speed computer screen.”
—Matt Graham (28:08)

Leaving the Agency and “Foundership” in Practice

(68:30–79:08)

• Endings and New Beginnings: Matt shares the story of his final days at the agency, the leadership summit on training/values, and how that solidified his focus on organizational “belief.”
• Personal Closure: Matt’s symbolic “pencil rubbing” of a fallen colleague’s star at CIA HQ marks his transition from national service to entrepreneurship.

“I took that dry erase marker and… I wrote down ‘What do we believe?’ ...If this is your mission and you believe it, then why do we have this problem?”
—Matt Graham (74:41)

• Why He Left: The inevitable bureaucracy—even in “high-speed” organizations—led to Matt, and others, confronting their own and the organization’s evolving values.

Building Ares Watches: An American Manufacturing Story

(80:19–129:32)

• From Passion to Plan: After leaving the agency, a family conversation about “What would you do if you could do anything?” leads Matt to make watches—his lifelong fascination.
• Purpose over Profit: Ares starts not as a business to maximize profit, but as a mission to make the best operational mission timer possible, inspired by the legacy of iconic field gear.
• Engineering Process: Matt details the challenges of truly building in America vs. just branding—hand-drawing cases and numerals, sourcing components, devising modular chassis to allow multiple movements.
• Field Testing and Community: Ares watches are heavily used in elite, operational environments, but rarely visible in public or social media due to client discretion.

“…Every part of that watch, we’re working to onboard more and more and more. Our dials, our lume, are Swiss because the Swiss make the best lume. But every chamfer, every angle, every part of that case sits the way it sits because I drew it that way.”
—Matt Graham (100:16)

• Business Approach: Pre-paying employees, leading with trust, and refusing to cut corners; Matt adopts practices learned from the CIA to solve problems “off the table.”
• Bespoke Manufacturing: Ares can make “batches of one,” customizing watches unlike mass brands, and seeing their field and diver watches recognized as new Mil-Spec standards.
• Next Steps: The “Liberty Project” aims to further bring manufacturing in-house, selling 2,500 watches to fund new infrastructure, with each buyer’s name embedded in Ares’s foundations.

Notable & Humorous Moments

• Sharpie Reticle Anecdote:
  Matt describes watching an agency instructor draw a shooting reticle on his hand with a Sharpie—demonstrating that wisdom and confidence often come in humble forms. (22:01–27:39)

• Presidential Shoe Incident:
  Andy and Matt recount President Bush dodging a shoe, then joking he wished he’d caught it, and Bush’s intervention to save the shoe thrower from execution by locals—insight into American values and leadership composure. (46:44–49:24)

• Red Watch Banter:
  A rolling joke about building a fully red watch for Andy, culminating in mockery, design tweaks, and the implications of “standing out” in operations. (85:57–89:42)

Timestamps for Important Segments

• Defining Foundership & Leadership: 10:34–23:00
• Career Path: Law Enforcement → Air Marshal → CIA: 29:30–68:30
• Inside Agency Selection, Culture & Training: 66:39–68:30
• Air Marshal Training/“Shoot for Pay” System: 42:08–44:19
• The Presidential Shoe Story & Agency Protection Lessons: 46:44–49:24
• Leaving the Agency—Leadership Whiteboard & Star Rubbing: 74:41–79:08
• Making Ares Watches—Philosophy, Process, and Challenges: 80:19–102:59
• Bespoke Manufacturing, Legacy, and Future Plans: 109:32–129:32

Selected Quotes

• “Foundership is a first principles discipline to steward belief across growth, time, context, all of that.”
  —Matt Graham (10:40)

• “What have I done today that gets me invited back tomorrow? ... This organization can have anybody they want—the best in the world.”
  —Matt Graham (71:08)

• “People who are wildly experienced… never took the attitude of ‘oh, you want to rely on your memory?’ Because the most experienced people know you can free up bandwidth.”
  —Andy Stumpf (27:06)

• “If you have made something…that performs…why would you change that? I’m not going to do that. We’ve made something that works and it performs.”
  —Matt Graham (125:19)

Where to Find Ares Watches

• areswatches.com
  • The home for Ares’s American-built field and diver watches, including info on the Liberty Project and bespoke ordering.

Takeaways

Matt Graham’s journey is one of relentless curiosity, learning, and a refusal to accept “this is just how things are done.” From patrol car to airplane to blacked-out SUV, he’s sought uncomfortable challenges, built skills layer by layer, and ultimately poured his energy into building tools for those on the front lines. His story illustrates that belief—in mission, in product, in people—remains the foundation of lasting, meaningful work.

For Further Listening

• Past episodes with founders, military/agency leaders, or operational gear designers.
• Future episodes on entrepreneurship, craftsmanship, and high-performance teams.

[End of Summary]