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Tactical Wealth: From Military to Money
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Tactical Wealth: From Military to Money

Author: Gebbia Media

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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.
36 Episodes
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What does it take to modernize the U.S. Navy from the inside? And what happens when the military starts thinking more like a startup?Justin Fanelli, Chief Technology Officer of the Department of the Navy, joins Tactical Wealth for an inside look at how the Navy is rethinking innovation, investing in emerging technologies, and working with the private sector to prepare for the future of warfare.From building a real estate business while working in intelligence to leading technology transformation within the Navy, Justin shares how his experience in both government and entrepreneurship shaped his approach to leadership and innovation. He breaks down why this may be one of the greatest times in history for veteran entrepreneurs, how AI is changing military operations, and why the next generation of defense innovation may come from startups rather than traditional defense contractors.Whether you're a veteran, entrepreneur, investor, or business leader, this conversation offers a rare perspective on the intersection of national security, technology, and entrepreneurship, straight from one of the people helping shape the Navy's future.👉 Subscribe to Tactical Wealth for more conversations on military service, entrepreneurship, investing, and leadership.EPISODE RESOURCESConnect with Justin Fanelli:💼 LinkedIn: Justin FanelliConnect with Kaj Larsen:🌐 Website: KajLarsen.com📸 Instagram: @KajLarsen💼 LinkedIn: Kaj LarsenJoin the Mission Money Community ➡️ https://mailchi.ch/siebert/valor-newsletter-signupSponsored by Blackout Coffee Co. Fresh coffee. Proudly supporting America's military community. Get 20% off your first order at blackoutcoffee.com/TacticalWealth
Retired U.S. Navy SEAL, bestselling author, and entrepreneur Jason Redman shares how surviving a life-threatening injury in Fallujah changed his perspective on leadership, purpose, and what it means to live greatly.After nearly 40 surgeries and four years of recovery, Jason rebuilt his life beyond the military, building businesses, investing in real estate, and helping fellow veterans navigate life after service. He breaks down the financial lessons he learned along the way and how he’s using technology and AI to help veterans access the benefits they’ve earned.We cover:Surviving combat and finding purpose after a second chance at lifeBuilding a nonprofit and navigating the financial realities of entrepreneurshipCreating multiple income streams and investing in real estateLessons from financial mistakes and building long-term wealthLaunching TurboVets to simplify veterans’ access to benefitsThe mindset behind overcoming adversity and living without regretWhether you're a veteran, entrepreneur, or business leader, Jason’s story offers powerful lessons on resilience, wealth-building, and making the most of the opportunities in front of you.👉 Subscribe to Tactical Wealth for more conversations on military service, entrepreneurship, investing, and leadership.EPISODE RESOURCESConnect with Jason Redman:🌐 Website: jasonredman.com📸 Instagram: @jasonredmanwwConnect with Kaj Larsen:🌐 Website: KajLarsen.com📸 Instagram: @KajLarsenJoin the Mission Money Community ➡️ https://mailchi.ch/siebert/valor-newsletter-signupSponsored by Blackout Coffee Co. Fresh coffee. Proudly supporting America’s military community. Get 20% off your first order at blackoutcoffee.com/TacticalWealth
In this episode of Tactical Wealth, Army Ranger, entrepreneur, and Co-Founder of Valor Hunt Club Drew Plateis shares how his experience in the 75th Ranger Regiment shaped his approach to entrepreneurship, leadership, and building businesses with a mission beyond profit.From growing up in New York and finding direction through military service to launching security companies, building luxury fashion and jewelry brands, and creating Valor Hunt Club, Drew explains how military discipline, adaptability, and learning through adversity helped him navigate the challenges of entrepreneurship and find a greater purpose in business.In this episode, we dive into:Finding Direction Through Military Service: How Drew’s difficult upbringing, exposure to the aftermath of 9/11, and early experiences with Army Rangers inspired him to pursue special operationsChoosing the Ranger Regiment: Why Drew pursued the Army Ranger pipeline, his desire to get into combat quickly, and what it took to earn his place in the 75th Ranger RegimentUnderstanding the Ranger Mission: How Rangers operate across land, sea, and air, take on high-value targets, and adapt to complex missions under pressureThe Entrepreneurial Mindset in the Military: Why Rangers learn to accomplish the most with the fewest resources and how that mentality builds confidence, creativity, and problem-solving skillsTransitioning Out of the Military: How injuries pushed Drew to leave active service and the challenges of rebuilding his identity, finding direction, and starting a new chapter as a civilianTaking Ownership of His Future: How Drew moved from working at a security firm to launching his own security business and learning to take responsibility for client acquisition, revenue, and business growthFinding Opportunity in Unlikely Industries: How Drew brought his military background into the luxury fashion and jewelry markets, combining tactical influences with high-end designLearning From Business and Failure: Why Drew measures entrepreneurial success by how much he learns rather than how much money he makes, and how each venture helped him better understand his strengths and prioritiesKnowing When to Pivot: How Drew approached exiting his luxury businesses and reinvesting in opportunities that aligned more closely with his values and long-term missionBuilding Businesses With Fellow Veterans: Why Drew believes military friendships, shared adversity, and the ability to give each other direct feedback can create a strong foundation for entrepreneurshipThe Story Behind Valor: How challenges with an earlier venture shaped Drew’s approach to funding, ownership, and building a business alongside fellow operatorsBuilding Valor Hunt Club: How Drew is creating a home for special operators to share their skills with the civilian community through training, outdoor experiences, and veteran employmentNature, Wellness, and Conservation: Why Drew wants Valor to provide a space for people to reconnect with nature, support their well-being, and contribute to conservation efforts in FloridaDefining Success Beyond Money: Why personal growth, self-awareness, and understanding how you can best contribute to society matter more than material markers of successRapid Fire: Drew shares his best investment, biggest financial mistake, the military skill that has helped him most in business, the habit he still carries from service, a book that shaped his thinking, and his morning routineWhether you're a veteran, entrepreneur, founder, or business leader, Drew’s story offers perspective on finding purpose after military service, building businesses through adversity, learning from failure, and using entrepreneurship to create opportunities for others.👉 Subscribe to Tactical Wealth for more conversations on military service, entrepreneurship, investing, wealth, leadership, and building with purpose.EPISODE RESOURCESConnect with Drew Plateis:🌐 Website: ValorHuntClub.com📸 Instagram: @pewlikedrew👤 LinkedIn: Andrew PlateisConnect with Kaj Larsen:🌐 Website: KajLarsen.com📸 Instagram: @KajLarsen👤 LinkedIn: Kaj LarsenJoin the Mission Money Community ➡️ https://mailchi.ch/siebert/valor-newsletter-signupTactical Wealth is supported by Blackout Coffee Co. Fresh coffee. Proudly supporting America’s military community. Get 20% off your first order at blackoutcoffee.com/TacticalWealth
In this episode of Tactical Wealth, Army veteran, entrepreneur, and ID.me co-founder and CEO Blake Hall shares how his experience leading soldiers in combat shaped his approach to leadership, problem-solving, and building a technology company focused on digital identity and fraud prevention.From serving as an infantry officer in Iraq to founding one of the leading digital identity platforms, Blake explains how lessons from the battlefield helped him navigate the uncertainty of entrepreneurship, recognize when to pivot, and build a company working to protect millions of Americans.In this episode, we dive into:Growing Up in an Army Family: How Blake’s family history of military service and desire to give back to his country led him to commission as an Army infantry officerLeading in Combat: How Blake’s deployment to Iraq challenged him as a leader and taught him to adapt under pressureLearning Through Failure: How Blake’s platoon improved its mission success rate by learning from mistakes, listening to the team, and continuously refining its approachThe Power of Teamwork: How collective intelligence, humility, and trusting the people around you can make the difference when the stakes are highFinding His Next Mission: How Blake transitioned from military service to Harvard Business School and searched for a new purpose beyond the battlefieldFrom Combat to Digital Identity: How his experience with intelligence systems and identifying threats in Iraq inspired the founding of ID.meOvercoming Entrepreneurial Doubt: How Blake navigated the uncertainty of starting a technology company without a technical background and learned to trust his ability to adaptBuilding a Business Around a Mission: How early supporters and investors backed Blake’s ability to learn and execute, even when they questioned his original business planKnowing When to Pivot: Why Blake shifted ID.me from a destination website focused on the military community to a broader digital identity platformScaling ID.me: How a pivotal product launch brought in 48,000 users in 45 days and helped demonstrate product-market fitFighting Fraud and Protecting Americans: How ID.me helps verify identities, prevent identity theft, and address national security threats, including attempts by North Korean operatives to obtain jobs at U.S. companiesDigital Identity, Privacy, and AI: Why strong identity verification matters online and how trusted digital identities could help people use AI agents to complete tasks across government and financial servicesMaking Benefits More Accessible: How ID.me created alternative identity verification options to help veterans, underserved communities, and people who cannot easily access in-person servicesRapid Fire: Blake shares his best investment, biggest financial mistake, the military skill that has helped him most in business, the habit he still follows, and a book that shaped his thinkingWhether you're a veteran, entrepreneur, founder, investor, or business leader, Blake’s story offers valuable perspective on finding purpose after service, learning through adversity, building trusted teams, and turning military experience into a mission that makes a difference.👉 Subscribe to Tactical Wealth for more conversations on military service, entrepreneurship, investing, wealth, leadership, and building with purpose.EPISODE RESOURCESConnect with Blake Hall:🌐 Website: ID.me👤 LinkedIn: Blake HallConnect with Kaj Larsen:🌐 Website: KajLarsen.com📸 Instagram: @KajLarsen👤 LinkedIn: Kaj LarsenJoin the Mission Money Community ➡️ https://mailchi.ch/siebert/valor-newsletter-signupTactical Wealth is supported by Blackout Coffee Co. Fresh coffee. Proudly supporting America’s military community. Get 20% off your first order at blackoutcoffee.com/TacticalWealth
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 birthdayThe Path to West Point: How an unlikely opportunity led Scott from Army enlistment to a presidential appointment at West PointMilitary Lessons in Entrepreneurship: How Scott’s service shaped the way he thinks about systems, innovation, and solving problemsStarting in the Car Business: How Scott went from helping friends buy cars to purchasing 10 to 15 vehicles a week while at UC BerkeleyBuilding His First Company: How Scott turned his side hustle into a real business and eventually sold it before graduating58 Companies Later: What Scott learned from decades of entrepreneurship, fundraising, and building businessesThe Future of AI: Why Scott believes AI could fundamentally change how consumers search for, finance, and purchase vehiclesAutonomous Vehicles: How self-driving technology could change mobility, ownership, insurance, and how people use their timeTurning Around TrueCar: How Scott took TrueCar from losing $2 million a month to making $2 million a month in one quarterBuilding Alignment: Why Scott interviewed all 400 employees before making major changes and focused on identifying who could help move the company forwardRapid 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 routineWhether 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 RESOURCESConnect with Scott Painter:🌐 TrueCar.com👤 LinkedIn: Scott PainterConnect with Kaj Larsen:🌐 Website: KajLarsen.com📸 Instagram: @KajLarsen👤 LinkedIn: Kaj LarsenJoin the Mission Money Community ➡️ https://mailchi.ch/siebert/valor-newsletter-signupTactical Wealth is supported by Blackout Coffee Co.Fresh coffee. Proudly supporting America’s military community.Get 20% off your first order at blackoutcoffee.com/TacticalWealth
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