Tactical Wealth: From Military to Money

In this episode of Tactical Wealth, Army veteran, serial entrepreneur, and TrueCar CEO and founder Scott Painter shares the unconventional path that took him from enlisting in the Army and serving as a Spanish interrogator and airborne soldier to building dozens of companies and reshaping the way consumers buy and own cars.

In this episode, we dive into:

Joining the Army: How Scott’s military family and desire for independence led him to enlist before his 17th birthday

The Path to West Point: How an unlikely opportunity led Scott from Army enlistment to a presidential appointment at West Point

Military Lessons in Entrepreneurship: How Scott’s service shaped the way he thinks about systems, innovation, and solving problems
Starting in the Car Business: How Scott went from helping friends buy cars to purchasing 10 to 15 vehicles a week while at UC Berkeley
Building His First Company: How Scott turned his side hustle into a real business and eventually sold it before graduating
58 Companies Later: What Scott learned from decades of entrepreneurship, fundraising, and building businesses
The Future of AI: Why Scott believes AI could fundamentally change how consumers search for, finance, and purchase vehicles
Autonomous Vehicles: How self-driving technology could change mobility, ownership, insurance, and how people use their time
Turning Around TrueCar: How Scott took TrueCar from losing $2 million a month to making $2 million a month in one quarter
Building Alignment: Why Scott interviewed all 400 employees before making major changes and focused on identifying who could help move the company forward
Rapid Fire: Scott shares his best investment, biggest financial mistake, the military habit he still relies on, the book that influenced his thinking, and his morning routine

Whether you're a veteran, entrepreneur, founder, investor, or simply interested in the future of technology and mobility, Scott’s story offers a firsthand look at building around real problems, challenging the status quo, and using technology to rethink an entire industry.

👉 Subscribe to Tactical Wealth for more conversations on military service, entrepreneurship, investing, wealth, technology, and building with purpose.

EPISODE RESOURCES

Connect with Scott Painter:
🌐 TrueCar.com

👤 LinkedIn: Scott Painter

Connect with Kaj Larsen:
🌐 Website: KajLarsen.com
📸 Instagram: @KajLarsen
👤 LinkedIn: Kaj Larsen

Join the Mission Money Community ➡️ https://mailchi.ch/siebert/valor-newsletter-signup

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In this episode of Tactical Wealth, Marine veteran, entrepreneur, and investor Paige Craig shares the unconventional path that took him from growing up dirt poor and serving in the Marine Corps to building a company in the middle of the Iraq War and eventually becoming a leading angel investor.

Paige opens up about growing up poor, his decision to leave West Point, and why he ultimately enlisted in the Marine Corps. He shares how his experience in the intelligence community exposed him to the frustrations of traditional military bureaucracy and led him to think differently about what was possible.

When he was told he wouldn’t deploy to Iraq anytime soon, Paige decided to create his own path into the war. With no company experience, investors, or significant capital, he started a company focused on providing intelligence and technology capabilities in conflict zones. He bootstrapped the business using credit cards and an equity line, traveled into Iraq, and built the operation from the ground up.

Paige talks about growing the company into a major defense business, the risks and challenges that came with operating in a war zone, and the lessons he learned about building something when there is no clear roadmap. He also explains why he eventually moved into venture capital and why he believes the most important investment is often the person behind the company.

In this episode, we dive into:

Growing Up Dirt Poor: How Paige’s early life and family’s military background shaped his path toward service and entrepreneurship

Leaving West Point: Why Paige realized the traditional military academy path wasn’t right for him and chose to enlist in the Marine Corps

From the Marine Corps to Intelligence: How Paige moved into the intelligence community and became frustrated with traditional bureaucracy and slow-moving systems

Building His Own Way Into Iraq: What happened when Paige was told he wouldn’t deploy and decided to start a company that could operate in war zones
Starting With Almost Nothing: How Paige bootstrapped the company without traditional investors, using credit cards and an equity line to get started
Building in a War Zone: How Paige traveled into Iraq, established his first headquarters, and built the company from the ground up
Scaling the Business: How the company grew into a major defense contractor and closed hundreds of millions of dollars in contracts during its first four years
The Reality of Entrepreneurship: The criticism, danger, and setbacks that came with building a company in a conflict zone
From Founder to Investor: Why Paige eventually sold the company and moved into venture capital
Betting on People: Why Paige believes founders matter more than decks, technology, or perfectly executed plans
No Battle Plan Survives: How Paige’s military experience shaped the way he works with founders when things inevitably go sideways
The Veteran Advantage: Why Paige believes veterans can bring a unique strategic advantage to entrepreneurship
The Future of Defense Tech: Paige’s perspective on how inexpensive technology is changing warfare and creating new opportunities in the defense industry
Rapid Fire: Paige shares his best investment, biggest financial mistake, the military habit he still relies on, his approach to lifelong learning, and what his daily routine looks like

Whether you're a veteran, entrepreneur, founder, investor, or simply interested in what it takes to build something from nothing, Paige’s story offers a firsthand look at taking an unconventional path, creating opportunity where none exists, and learning to figure things out along the way.

👉 Subscribe to Tactical Wealth for more conversations on military service, entrepreneurship, investing, wealth, and building with purpose.

EPISODE RESOURCES

Connect with Paige Craig:
📸 LinkedIn: Paige Craig

📸 Instagram: @outlandervc

Connect with Kaj Larsen:
🌐 Website: KajLarsen.com
📸 Instagram: @KajLarsen
👤 LinkedIn: Kaj Larsen

Join the Mission Money Community ➡️ https://mailchi.ch/siebert/valor-newsletter-signup

In this episode of Tactical Wealth, former Navy SEAL, entrepreneur, and Defense Strategies Group founder Mike O’Dowd shares the unconventional path that took him from nearly a decade in the SEAL Teams to building his own security and training company.

Mike opens up about his time in the SEAL Teams, serving in Iraq and Afghanistan, and the lessons he carried with him after leaving the military. He shares what happened when he moved into the corporate world, why he struggled with the siloed nature of traditional business, and the moment he realized he needed to build something of his own.

Then came 2020. Mike’s company went under with roughly 12 hours’ notice. With little savings and no clear safety net, he took two unemployment checks before deciding to start teaching shooting classes through Instagram. His first class sold out, but the road from there was anything but easy.

Mike talks about why he kept going through setbacks, what the SEAL Teams taught him about grit and commitment, and why he believes success comes down to seeing things through to the end.

In this episode, we dive into:

Nearly a Decade in the SEAL Teams: What Mike learned from his time serving in Iraq and Afghanistan and teaching combatives and weapons

The Transition Out of the Military: Why Mike struggled with corporate environments and eventually realized he needed to build something for himself

The 12-Hour Notice: What happened when Mike’s company went under in 2020 and left him without a financial safety net
Starting From Scratch: How teaching shooting classes through Instagram became the beginning of Mike’s next chapter
The $11,000 Setback: How Mike’s first range class ended with a broken-down Land Cruiser and a massive repair bill
Losing $30,000 in Gear: The setback that came when his truck and trailer were stolen and why he refused to quit
The Power of Commitment: Why Mike believes you have to go all in and see things through to the end
What the SEAL Teams Taught Him: How BUD/S and the Teams taught Mike to keep showing up even when things get difficult
Knowing When to Pivot: Why commitment doesn’t mean refusing to change course when a better opportunity appears
Building Defense Strategies Group: How Mike turned his experience into a security and training company serving everyone from beginners to elite SWAT teams

The Military-to-Entrepreneurship Connection: How the military mindset of finding a way to complete the mission translates into building a business
The Cost of Playing It Safe: Why Mike believes getting too comfortable can keep you from reaching your full potential
Advice for Veterans: Mike’s perspective on commitment, risk, failure, and building something of your own after service

Whether you're a veteran, entrepreneur, business owner, or simply interested in the mindset behind building something from the ground up, Mike’s story offers a firsthand look at what it takes to keep moving when the plan falls apart.

👉 Subscribe to Tactical Wealth for more conversations on military service, entrepreneurship, investing, wealth, and building with purpose.

EPISODE RESOURCES

Connect with Mike O’Dowd:
🌐 Website: www.defensestrategies.us

📸 Instagram: @mike_oscar_delta
👤 LinkedIn: Michael O'Dowd

Connect with Kaj Larsen:
🌐 Website: KajLarsen.com
📸 Instagram: @KajLarsen
👤 LinkedIn: Kaj Larsen

Join the Mission Money Community ➡️ https://mailchi.mp/siebert/valor-newsletter-signup

In this episode of Tactical Wealth, Army veteran, entrepreneur, venture capitalist, and Moonshots Capital General Partner Craig Cummings shares the unconventional path that took him from nearly 17 years in military intelligence to building companies, investing in founders, and creating wealth within the military veteran community.

Craig opens up about growing up in a military family, his time at West Point, and the decision to leave the Army before reaching 20 years of service. He shares what it was like going from the structure and safety net of the military to the uncertainty of entrepreneurship, including the early days of a startup that was just 45 days away from running out of cash.

Today, Craig and his team evaluate thousands of companies while looking for the founders and teams they believe have what it takes to build something extraordinary. He shares what he looks for before investing, why teams ultimately matter more than individual founders, and the qualities that separate the companies he backs from the thousands he passes on.

In this episode, we dive into:

Growing Up in a Military Family: How Craig's family shaped his path toward West Point and military service

17 Years in the Army: What Craig learned from nearly two decades in military intelligence, including working with the NSA and JSOC

Leaving Before 20 Years: Why Craig decided to transition out of the Army before reaching a traditional military retirement

The Leap Into Entrepreneurship: What it was like trading the military's safety net for the uncertainty of building a company

45 Days of Cash: The high-stakes moment when Craig's startup was nearly out of money and needed to land purchase orders

Building for the Battlefield: How Craig and his team worked to bring cellular network technology to the battlefield

The Entrepreneurial Mindset: Why Craig believes veterans are uniquely positioned to take the risk of entrepreneurship
From Operator to Investor: How Craig went from building companies to writing angel checks and eventually launching Moonshots Capital
Building Moonshots Capital: How Craig and Kelly Perdue turned investing from a side hustle into a venture capital firm
The Investment Strategy: What Craig and his team look for when deciding which companies to back
The Power of Teams: Why Craig believes teams ultimately win over individual founders
Investing in Veterans: Why Moonshots Capital has a strong connection to veteran founders and the military community
The Future of Defense Tech: Why Craig believes the Pentagon and private technology sector need to work together differently
Advice for Veterans: Why Craig encourages veterans to take the risk of entrepreneurship and understand that failure doesn't mean the end of their career

Whether you're a veteran, entrepreneur, investor, founder, or simply interested in building wealth and creating impact, Craig's story offers a firsthand look at what it takes to turn military experience into entrepreneurship, investing, and a new form of service.

👉 Subscribe to Tactical Wealth for more conversations on military service, entrepreneurship, investing, wealth, technology, and building with purpose.

EPISODE RESOURCES

Connect with Craig Cummings:
🌐 Moonshots Capital: moonshotscapital.com

🌐Blog: medium.com/leadership-prevails

Connect with Kaj Larsen:
🌐 Website: KajLarsen.com
📸 Instagram: @KajLarsen
👤 LinkedIn: Kaj Larsen

Join the Mission Money Community➡️ https://mailchi.mp/siebert/valor-newsletter-signup

In this episode of Tactical Wealth, Air Force Master Sergeant, combat cameraman, Columbia neuroscience graduate, and Bastogne AI co-founder Greg Brook shares the unconventional path that took him from working on the F-22 to documenting combat operations, studying neuroscience, advising defense tech companies, and building a company focused on the future of warfare.

Greg opens up about why he joined the Air Force, how a chance encounter introduced him to the world of combat camera, and what it was like deploying alongside some of the military’s most elite units. He also shares the experience that pushed him toward neuroscience and a deeper understanding of military mental health.

In this episode, we dive into:

Joining the Air Force: Why Greg enlisted in 2006 and initially planned to become a Marine

Working on the F-22: What Greg learned from working with one of the world's most advanced fighter aircraft

Discovering Combat Camera: How a chance encounter introduced Greg to a career documenting frontline operations alongside elite military units

Inside Combat Camera: What it's like to deploy with Special Operations forces and capture some of the most consequential moments of the Global War on Terror

The Cost of War: The experiences that led Greg to question how the military approaches mental health and veteran suicide

Why Neuroscience: How a devastating moment during a deployment pushed Greg toward studying neuroscience at Columbia
The Columbia Experience: How Greg balanced an Ivy League education with continued military service and deployments around the world
From Ukraine to Defense Tech: How working alongside humanitarian and medical teams helped Greg discover the defense technology ecosystem

The Problem With Defense Tech: Why Greg believes too many companies are building technology without first understanding what warfighters actually need
Building Bastogne AI: How Greg and his co-founder identified a critical problem around AI, compute, communications, and infrastructure in modern warfare
The Future of Warfare: Why AI, autonomous systems, and edge computing are changing how militaries operate
Building for the User: Why Greg believes defense companies should start by asking the people on the ground what problems actually need to be solved
Listening to Experience: Why Greg believes entrepreneurs should listen when someone with more experience tells them they're making a mistake
The Mission Behind Bastogne: Why Greg's ultimate goal is to help bring service members home alive and reduce the human cost of war
Advice for Veterans: What Greg would tell service members transitioning into the private sector or considering entrepreneurship

Whether you're a veteran, entrepreneur, technologist, investor, or simply interested in the future of warfare, Greg's story offers a unique look at military service, innovation, neuroscience, and building with purpose.

👉 Ready to stay tactical and stay driven? Hit SUBSCRIBE for more conversations on military service, entrepreneurship, wealth, technology, and building a life of purpose.

EPISODE RESOURCES

Connect with Greg Brook:
🌐 Website: www.bastogne.ai
📸 Instagram: @avantgarde.operator
👤 LinkedIn: Gregory Brook
𝕏 Twitter/X: @BastogneActual

Connect with Kaj Larsen:
🌐 Website: kajlarsen.com
📸 Instagram: @KajLarsen
👤 LinkedIn: Kaj Larsen

Join the Mission Money Community ➡️ https://mailchi.mp/siebert/valor-newsletter-signup

In this episode of Tactical Wealth, former U.S. Navy SEAL, FBI agent, entrepreneur, and author Errol Doebler shares the unconventional journey that took him from the Naval Academy and SEAL Teams to the FBI, entrepreneurship, and building his own leadership philosophy.

Errol opens up about fighting his way into the SEAL Teams after initially being denied a billet, the lessons he learned from his time in the Fleet Navy, and the experiences that shaped him as a leader. He also gets candid about the injuries that ultimately ended his military career, the difficult transition that followed, and how a traumatic brain injury changed the way he understood that chapter of his life.

From selling copiers to working cases at the FBI and deploying to Afghanistan with the 75th Ranger Regiment, Errol explains how each chapter of his career prepared him for entrepreneurship. He shares why sales is one of the best proving grounds for building a business, why every entrepreneur is constantly selling, and what finally pushed him to become the captain of his own ship.

In this episode, we dive into:

Fighting His Way Into the SEAL Teams: How Errol went from missing out on a SEAL billet at the Naval Academy to earning his way to BUD/S

Learning the Grind: The leadership lessons Errol learned from serving in the Fleet Navy and leading sailors with very different levels of motivation
The Cost of Service: How injuries sustained during training and an operation ultimately changed the course of Errol's military career
Losing Your Mission: What it felt like to leave the SEAL Teams after building his identity around military service
Understanding His Injury: How recognizing his traumatic brain injury helped Errol make sense of the struggles he experienced after leaving the military
Starting Over in Sales: Why Errol's first jobs in the private sector taught him lessons that would later become critical to entrepreneurship
September 11th & the FBI: How 9/11 changed Errol's path and led him back into federal service
Inside the FBI: What Errol learned working terrorism, Russian organized crime, and gang cases, and why the bureaucracy eventually pushed him toward entrepreneurship
Serving in Afghanistan: Errol's experience supporting the 75th Ranger Regiment and conducting combat operations alongside elite military units
Building Ice Cold Leader: How Errol turned the lessons from his military, law enforcement, and personal experiences into a leadership philosophy and book

The Ice Cold Leader Mindset: How cold exposure, breathing, and the Wim Hof Method became part of Errol's journey toward rebuilding himself
The Entrepreneurial Transition: Why Errol believes every entrepreneur is ultimately selling something and how sales became a proving ground for his next chapter
Leadership & Accountability: Why professionalism, planning, accountability, and setting high standards matter more than simply trying to be liked
Money Lessons: The financial mistake Errol still remembers, the importance of planning, and the military habits he carries into entrepreneurship
Finding the Next Mission: How Errol learned to take ownership of his future after losing the career he thought he would have

Whether you're a veteran, entrepreneur, leader, or someone navigating a major career transition, Errol's story is a powerful look at resilience, identity, leadership, and finding your next mission when life doesn't go according to plan.

👉 Ready to stay tactical and stay driven? Hit SUBSCRIBE and join us for more conversations on leadership, wealth, entrepreneurship, military service, and building a life of purpose.

EPISODE RESOURCES

Connect with Errol Doebler:
🌐 Website: icecoldleader.com
📸 Instagram: @the_ice_cold_leader
👤 LinkedIn: Errol Doebler

Connect with Kaj Larsen:
🌐 Website: kajlarsen.com
📸 Instagram: @KajLarsen
👤 LinkedIn: Kaj Larsen

Join the Mission Money Community ➡️ https://mailchi.mp/siebert/valor-newsletter-signup

In this episode of Tactical Wealth, former NFL player, U.S. Navy SEAL, and inspiring entrepreneur Clint Bruce shares his unconventional journey from the football field to the SEAL Teams and into the boardroom.

Clint opens up about why he chose to leave a promising NFL career to pursue the SEAL Teams, the lessons he carried from the battlefield into business, and how surrounding himself with people he could learn from shaped every chapter of his life.

He also gets candid about the challenges of transitioning out of the military and entering the business world, including why he found the boardroom more lonely and intimidating than the ball field or battlefield.

In this episode, we dive into:

🇺🇸 From NFL to SEAL Teams: Why Clint walked away from professional football to pursue a harder path

⚔️ Choosing the Harder Path: How Clint's desire to discover what he was made of shaped his biggest decisions

🧠 Preparation & Performance: Why thousands of reps can prepare you for moments you never expected

🤝 Chasing the Right People: How surrounding yourself with people he couldn't keep up with helped Clint grow throughout his career

🎯 The Power of a Map: Why Clint believes that having a map means you may be wrong, but you won't be lost

🏢 The Boardroom vs. the Battlefield: Why Clint says the boardroom was the loneliest and scariest environment he ever experienced

💼 Building Businesses: How Clint transitioned his military experience into entrepreneurship and began building companies

📈 Economic Counterinsurgency: Why Clint believes veterans can use their skills to help rebuild the communities and places that shaped them

👨‍👩‍👧 Family & Stewardship: How Clint thinks about time, leadership, marriage, fatherhood, and making the people he loves proud
💰 Money as a Resource: Why changing the way he viewed money helped Clint make better financial decisions
🎖️ Leadership & Legacy: Why the best leaders focus on building people who can eventually surpass them

Whether you're a veteran, entrepreneur, leader, athlete, or someone considering a major career transition, Clint shares hard-earned lessons on risk, leadership, resilience, purpose, and choosing the harder path.

👉 Ready to stay tactical and stay driven? Hit SUBSCRIBE and join us for more conversations on leadership, wealth, entrepreneurship, military service, and building a life of purpose.

EPISODE RESOURCES

Connect with Clint Bruce:
📸 Instagram: @realclintbruce
👤 LinkedIn: Clint Bruce

Connect with Kaj Larsen:
🌐 Website: kajlarsen.com
📸 Instagram: @KajLarsen
👤 LinkedIn: Kaj Larsen

Join the Mission Money Community ➡️ https://mailchi.mp/siebert/valor-newsletter-signup

In this episode of Tactical Wealth, former U.S. Navy SEAL Ryan Williams shares his unconventional journey from the SEAL Teams to becoming a serial entrepreneur and building multiple successful businesses.

Ryan opens up about the realities of entrepreneurship, from starting his first clothing company with virtually no business experience to making mistakes, selling companies, and eventually building Industry Threadworks. He explains why he believes entrepreneurship is even harder than being a Navy SEAL and how learning to recognize patterns, adapt, and keep moving forward shaped his approach to business.

Ryan also gets candid about one of his biggest business failures, when rapid expansion left his company hundreds of thousands of dollars in debt. He shares what went wrong, how he recovered, and why knowing when to pivot can be just as important as refusing to quit.

In this episode, we dive into:

🇺🇸 From SEAL Teams to Entrepreneurship: How Ryan transitioned from military service into business and discovered entrepreneurship through trial and error
📈 Building Multiple Businesses: How Ryan went from his first clothing company to launching and selling multiple companies
💰 The Reality of Growth: Why growing revenue doesn't always mean having more money and why businesses can become financially dangerous as they scale
⚠️ Learning From Failure: How expanding too quickly nearly put Ryan's company out of business and what he learned from the experience
🧠 Pattern Recognition: Why experience can help entrepreneurs recognize when something isn't working and when to step back
🔄 Knowing When to Pivot: Why quitting an idea isn't the same as quitting on yourself
🤝 Partnership & Leadership: How Ryan learned to define roles, build systems, and surround himself with people who complement his strengths
💼 The Power of a Day Job: Why Ryan believes keeping a job while building a business can actually give entrepreneurs a major advantage
💵 Financial Freedom: How having money can provide the freedom to make better decisions when things get difficult
🎯 Taking the First Step: Why aspiring entrepreneurs shouldn't try to map out every step before they begin

Whether you're a veteran, entrepreneur, founder, or someone considering a new path after military service, Ryan shares hard-earned lessons on resilience, failure, leadership, financial discipline, and building something from the ground up.

👉 Ready to stay tactical and stay driven? Hit SUBSCRIBE and join us for more conversations on leadership, wealth, entrepreneurship, and building a life of purpose.

EPISODE RESOURCES

Connect with Ryan Williams:
📸 Instagram: @invictus5326
🌐 Industry Threadworks: IndustryThreadworks.com
🌐 Archive: archive3pl.com
👤 LinkedIn: Ryan Williams

Connect with Kaj Larsen:
🌐 Website: kajlarsen.com
📸 Instagram: @KajLarsen
👤 LinkedIn: Kaj Larsen

Join the Mission Money Community ➡️ https://mailchi.mp/siebert/valor-newsletter-signup

In this episode of Tactical Wealth, former U.S. Navy SEAL Max Darsonval shares how his journey from elite military service to entrepreneurship led him to found Velocity AI, a company focused on transforming human performance through artificial intelligence.

After serving 12 years as a Navy SEAL, Max faced the challenge of transitioning from military life to entrepreneurship. Drawing on the lessons learned in the Teams, he set out to solve a problem he experienced firsthand: making elite performance coaching and training more accessible through technology.

Max discusses the discipline required to succeed in special operations, the mindset shift that comes with leaving the military, and what it takes to build an AI company from the ground up. He also shares how Velocity AI is helping athletes, tactical professionals, and everyday individuals train smarter by using data to personalize performance and recovery.

In this episode, we dive into:
🇺🇸 Life After the SEAL Teams: The challenges of transitioning from military service into entrepreneurship.
🤖 Creating Velocity AI: Why Max believes artificial intelligence is the future of human performance.
💪 Training Smarter: How data-driven coaching can help people unlock their full potential.
📈 Building a Startup: Lessons from launching a company, overcoming setbacks, and learning through trial by fire.
🧠 The Operator Mindset: How discipline, adaptability, and resilience continue to shape Max's approach to business.
⚡ Performance Beyond the Military: Why elite training principles shouldn't be limited to special operations or professional athletes.
🚀 Innovation Through Service: How solving real-world problems became Max's next mission after the Navy SEALs.
💡 Leadership That Evolves: Why continuous learning and embracing discomfort are essential for long-term success.

Whether you're a veteran, entrepreneur, athlete, founder, or someone striving to reach your full potential, Max shares valuable insights on leadership, innovation, resilience, and the future of human performance.

👉 Ready to stay tactical and stay driven? Hit SUBSCRIBE and join us for more conversations on leadership, wealth, and building a life of purpose.

EPISODE RESOURCES

Connect with Max Darsonval:
💼 LinkedIn: Max Darsonval
📸 Instagram: @vlcty_ai

Connect with Kaj Larsen:
🌐 Website: kajlarsen.com
📸 Instagram: @KajLarsen
👤 LinkedIn: Kaj Larsen

Join the Mission Money Community➡️ https://mailchi.mp/siebert/valor-newsletter-signup

In this episode of Tactical Wealth, former Marine Corps infantry officer Zach Iscol shares how a career built on service led him from the Battle of Fallujah to founding one of the nation's largest veteran mental health organizations and ultimately serving as New York City's Emergency Management Commissioner.

After graduating from Cornell, Zach commissioned into the Marine Corps just one month before September 11th. He volunteered for the infantry, fought in the Battle of Fallujah, helped build the Marine Corps' special operations pipeline, and learned leadership lessons that would shape every chapter of his career.

Following his military service, Zach noticed a growing crisis. Veterans were dying by suicide at alarming rates while access to mental health care remained difficult and stigmatized. That realization led him to found the Headstrong Project, providing veterans with world-class mental health care at no cost and without bureaucracy.

Zach also discusses launching Task & Purpose, building organizations inside existing institutions, leading New York City through emergencies ranging from cyberattacks and extreme weather to the migrant crisis, and why leadership is ultimately about serving the people around you.

In this episode, we dive into:

🇺🇸 From Marine to Public Servant: How combat leadership prepared Zach to lead long after leaving the military.

🧠 Changing Veteran Mental Health Care: Why he founded the Headstrong Project and how it transformed access to care.

🚀 Building Organizations That Matter: Lessons from launching nonprofits, media companies, and mission-driven ventures.

🏙️ Leading New York City Through Crisis: What it takes to manage emergencies affecting millions of people.

📈 Entrepreneurship Beyond the Garage: Why not every startup begins from scratch and how to build inside existing organizations.

💡 Leadership That Scales: The importance of humility, taking care of your people, and creating teams built on trust.

📊 Learning From Failure: Why listening to customers, embracing setbacks, and pivoting early are essential to success.
⚡ Military Lessons That Last: How the Marine Corps shaped Zach's approach to leadership, resilience, and decision-making.

Whether you're a veteran, entrepreneur, founder, public servant, or someone looking to build a mission-driven career, Zach shares powerful lessons on leadership, entrepreneurship, resilience, and creating lasting impact.

👉 Ready to stay tactical and stay driven? Hit SUBSCRIBE and join us for more conversations on leadership, wealth, and building a life of purpose.

EPISODE RESOURCES

Connect with Zach Iscol:
💼 LinkedIn: Zachary Iscol
📸 Instagram: @zachiscol

Connect with Kaj Larsen:
🌐 Website: kajlarsen.com
📸 Instagram: @KajLarsen
👤 LinkedIn: Kaj Larsen