Tactical Wealth: From Military to Money

About Tactical Wealth: From Military to Money

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.

Publisher

Gebbia Media

Category

business · education

Language

en

Explicit

No

First episode

10 Jun 2025

Latest episode

6 Oct 2026

Latest episodes

33 episodes in the feed.

1. 

   6 Oct 2026

   Reinventing the Car Industry by Turning a Real-World Problem Into a Business | Scott Painter

   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 (https://mailchi.ch/siebert/valor-newsletter-signup)

2. 

   29 Sept 2026

   Building a Company in a War Zone and Becoming a Leading Angel Investor | Paige Craig

   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 (https://mailchi.ch/siebert/valor-newsletter-signup)

3. 

   22 Sept 2026

   Find a Way or Make One: Navy SEAL on Losing Everything to Building a Defense Empire | Mike O’Dowd

   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 (http://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 (https://mailchi.mp/siebert/valor-newsletter-signup)

Who has been a guest on Tactical Wealth: From Military to Money

Names identified in recent episode analyses. Showing up to five guests.

• Mitch Aguiar
• Dr Brenden Borrowman
• Patrick J Murphy

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

4 ratings

Spotify

5.0 / 5

8 ratings

Podcast Authority Score: 53 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

94

Social presence

0

YouTube

0

Engagement

32

Contact Tactical Wealth: From Military to Money

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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