Tactical Wealth: From Military to Money

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.

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

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