Tactical Wealth: From Military to Money

Gebbia Media
  • 5.0 (4)
  • Entrepreneurship

Tactical Wealth is the show built to empower the military and veteran community to take control of their financial future. From navigating the military to civilian life transition, to launching businesses, growing your income, and building long-term wealth, each episode brings you real stories and actionable insights from those who’ve gone from boots on the ground to building lasting wealth. Hosted by Kaj Larsen, former Navy SEAL, award-winning journalist, and mission-driven entrepreneur. Kaj successfully co-founded a financial technology company and sold the company in 2024. The podcast features hard truth conversations with successful veteran entrepreneurs, CEOs, and top financial experts. Whether you're still in uniform or already charting your next chapter, this podcast gives you the tactical tools to lead with impact in your finances and beyond. Let’s get tactical. Tactical Wealth is a Gebbia Media production, brought to you by Siebert.Valor, a military-focused initiative from Siebert Financial. The Tactical Wealth podcast is for informational and entertainment purposes only. The views expressed by guests are their own and do not necessarily reflect those of Siebert Financial. This podcast does not constitute investment advice, an offer to sell, or a solicitation to buy any securities. Past performance is not indicative of future results. Listeners should consult a qualified financial professional before making any investment decisions. For more information and disclosures, please visit siebert.com/disclosures.

  1. 5d ago

    Inside the Mind of a Combat Cameraman Building the Future of Warfare | Greg Brook

    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 ColumbiaThe Columbia Experience: How Greg balanced an Ivy League education with continued military service and deployments around the worldFrom 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 needBuilding Bastogne AI: How Greg and his co-founder identified a critical problem around AI, compute, communications, and infrastructure in modern warfareThe Future of Warfare: Why AI, autonomous systems, and edge computing are changing how militaries operateBuilding for the User: Why Greg believes defense companies should start by asking the people on the ground what problems actually need to be solvedListening to Experience: Why Greg believes entrepreneurs should listen when someone with more experience tells them they're making a mistakeThe Mission Behind Bastogne: Why Greg's ultimate goal is to help bring service members home alive and reduce the human cost of warAdvice 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 Brook𝕏 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

    Inside the Mind of a Combat Cameraman Building the Future of Warfare | Greg Brook

  2. Sep 1

    How the Ice Cold Leader Rebuilt His Life After Everything Changed | Errol Doebler

    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 motivationThe Cost of Service: How injuries sustained during training and an operation ultimately changed the course of Errol's military careerLosing Your Mission: What it felt like to leave the SEAL Teams after building his identity around military serviceUnderstanding His Injury: How recognizing his traumatic brain injury helped Errol make sense of the struggles he experienced after leaving the militaryStarting Over in Sales: Why Errol's first jobs in the private sector taught him lessons that would later become critical to entrepreneurshipSeptember 11th & the FBI: How 9/11 changed Errol's path and led him back into federal serviceInside the FBI: What Errol learned working terrorism, Russian organized crime, and gang cases, and why the bureaucracy eventually pushed him toward entrepreneurshipServing in Afghanistan: Errol's experience supporting the 75th Ranger Regiment and conducting combat operations alongside elite military unitsBuilding 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 himselfThe Entrepreneurial Transition: Why Errol believes every entrepreneur is ultimately selling something and how sales became a proving ground for his next chapterLeadership & Accountability: Why professionalism, planning, accountability, and setting high standards matter more than simply trying to be likedMoney Lessons: The financial mistake Errol still remembers, the importance of planning, and the military habits he carries into entrepreneurshipFinding 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

    How the Ice Cold Leader Rebuilt His Life After Everything Changed | Errol Doebler

  3. Aug 25

    Choosing the Harder Path: NFL Player Turned SEAL Turned Entrepreneur | Clint Bruce

    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

    Choosing the Harder Path: NFL Player Turned SEAL Turned Entrepreneur | Clint Bruce

  4. Aug 18

    The Lessons Nobody Teaches You: Navy SEAL’s Unconventional Journey to Entrepreneur | Ryan Williams

    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

    The Lessons Nobody Teaches You: Navy SEAL’s Unconventional Journey to Entrepreneur | Ryan Williams

  5. Aug 11

    Navy SEAL Turned Founder: Creating the Future of Human Performance with Velocity AI | Max Darsonval

    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

    Navy SEAL Turned Founder: Creating the Future of Human Performance with Velocity AI | Max Darsonval

  6. Aug 4

    How a Marine Veteran Led NYC Through Crisis and Built an Organization That Saved Lives | Zach Iscol

    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

    How a Marine Veteran Led NYC Through Crisis and Built an Organization That Saved Lives | Zach Iscol

  7. Jul 28

    How a Navy Nuke Built the Company Transforming the Drone Industry | Will Hasting

    In this episode of Tactical Wealth, former U.S. Navy nuclear engineer Will Hasting reveals how he went from operating nuclear reactors to building the next generation of drones. Growing up on a dairy farm in rural Illinois, Will enlisted in the Navy at just 17 years old. After earning a spot in the Navy's elite nuclear program, he learned firsthand how discipline, technical excellence, and operating under extreme pressure could shape a career far beyond military service. Following the Navy, Will accelerated through an aerospace engineering degree, designed IndyCars, developed jet engines at GE Aerospace, helped take a Silicon Valley startup from Series C to IPO, and ultimately founded Angel Aerial Systems to solve one of the biggest challenges in modern drone technology. Will shares how one conversation with a Navy chief changed the trajectory of his life, why your environment determines your future, and how military training prepared him to build cutting-edge technology with real-world impact. In this episode, we dive into:🚁 From Navy Nuke to CEO: How the Navy's nuclear program built the foundation for Will's career in engineering and entrepreneurship.🧠 The Power of Your Environment: Why changing who you surround yourself with can completely change your future.⚙️ Engineering Under Pressure: How operating nuclear reactors prepared him to lead startups through uncertainty.🏎️ Building the Impossible: From designing IndyCars and jet engines to creating next-generation drones.🚀 Starting a Company From Scratch: Why solving customer problems matters more than chasing technology.🇺🇸 Innovation for National Security: How Angel Aerial Systems is developing mission-focused drones for military and civilian applications.💰 Lessons on Wealth & Entrepreneurship: Why taking outside investment changed the way he thinks about responsibility, leadership, and success.⚡ Military Skills That Win in Business: Extreme ownership, attention to detail, and staying calm when everything is on the line. Whether you're a veteran, entrepreneur, engineer, investor, or someone building your next mission, Will shares powerful lessons on leadership, resilience, innovation, and turning technical expertise into 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 RESOURCESConnect with Will Hasting:🌐 Website: angelaerialsystems.com💼 LinkedIn: Will Hasting Connect with Kaj Larsen:🌐 Website: kajlarsen.com📸 Instagram: @KajLarsen👤 LinkedIn: Kaj Larsen

    How a Navy Nuke Built the Company Transforming the Drone Industry | Will Hasting

  8. Jul 21

    Navy SEAL Commander: How Military Service Fueled His Mission to Support Veterans | Jimmy May

    In this episode of Tactical Wealth, we sit down with retired Navy SEAL Commander, CEO, & Founder Jimmy May. After 22 years in the SEAL Teams, Jimmy transitioned from leading elite military teams to building businesses and creating opportunities for veterans searching for their next mission as CEO of Beyond the Brotherhood. Jimmy shares how a mentor changed the trajectory of his life, why he believes veterans don’t need handouts but opportunities, and how the leadership lessons he learned in the military became the foundation for his work after service. From founding veteran-focused initiatives to building his own company, Mayday Executive Services, Jimmy explains how he applied the SEAL mindset of discipline, risk management, and resilience to entrepreneurship. In this episode, we dive into: 🎖️ From Navy SEAL to Entrepreneur: How Jimmy’s 22 years in the Navy shaped his leadership style, decision-making, and approach to business. 🤝 The Power of Mentorship: How finding the right mentor became one of the most important investments of his life and inspired him to help others. 🇺🇸 A New Mission After Service: Why Jimmy dedicated himself to creating opportunities for veterans transitioning into civilian life.🚀 Building Businesses With Purpose: How Jimmy launched companies by starting small, keeping overhead low, and focusing on creating real value.⚔️ The SEAL Mindset in Business: How understanding risk, adapting under pressure, and taking action helped him navigate entrepreneurship.🪜 Not a Handout, a Leg Up: Why veterans need opportunities, support, and a pathway to build their next chapter.📈 Taking the First Step: Jimmy’s advice for veterans and aspiring entrepreneurs looking to start something new.🌎 Building the Next Generation: How Jimmy is creating a legacy by helping the people coming behind him succeed. Whether you’re a veteran, entrepreneur, investor, or someone looking to build your next mission, Jimmy May shares powerful lessons on leadership, resilience, mentorship, and creating impact beyond the battlefield. 👉 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 Jimmy May:🌐 Website: www.beyondthebrotherhood.org 🌐 Website: www.maydayexecutive.com💼 LinkedIn: Jimmy May Connect with Kaj Larsen:🌐 Website: kajlarsen.com📸 Instagram: @KajLarsen👤 LinkedIn: Kaj Larsen

    Navy SEAL Commander: How Military Service Fueled His Mission to Support Veterans | Jimmy May
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Tactical Wealth is the show built to empower the military and veteran community to take control of their financial future. From navigating the military to civilian life transition, to launching businesses, growing your income, and building long-term wealth, each episode brings you real stories and actionable insights from those who’ve gone from boots on the ground to building lasting wealth. Hosted by Kaj Larsen, former Navy SEAL, award-winning journalist, and mission-driven entrepreneur. Kaj successfully co-founded a financial technology company and sold the company in 2024. The podcast features hard truth conversations with successful veteran entrepreneurs, CEOs, and top financial experts. Whether you're still in uniform or already charting your next chapter, this podcast gives you the tactical tools to lead with impact in your finances and beyond. Let’s get tactical. Tactical Wealth is a Gebbia Media production, brought to you by Siebert.Valor, a military-focused initiative from Siebert Financial. The Tactical Wealth podcast is for informational and entertainment purposes only. The views expressed by guests are their own and do not necessarily reflect those of Siebert Financial. This podcast does not constitute investment advice, an offer to sell, or a solicitation to buy any securities. Past performance is not indicative of future results. Listeners should consult a qualified financial professional before making any investment decisions. For more information and disclosures, please visit siebert.com/disclosures.

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