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.
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EPISODE RESOURCES
Connect with Paige Craig:
📸 LinkedIn: Paige Craig
📸 Instagram: @outlandervc
Connect with Kaj Larsen:
🌐 Website: KajLarsen.com
📸 Instagram: @KajLarsen
👤 LinkedIn: Kaj Larsen
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