From Special Ops Pilot to Defense Innovator: Lessons from Forrest Underwood

I recently had the privilege of sitting down with Forrest Underwood, and let me tell you—his story is one you don’t hear every day. Forrest went from bagging groceries in high school to becoming a U.S. Air Force Academy graduate, flying MC-130Js for Special Operations, and later stepping into some of the most complex corners of defense technology, venture capital, and government acquisition. Today, he’s serving as Chief of Joint Investment Strategies at the Office of the Secretary of Defense.

But what really stood out to me in this conversation wasn’t just Forrest’s résumé—it was how his journey sheds light on the massive challenges and opportunities that exist in defense contracting today. Whether you’re a founder, a tech leader, or someone trying to break into government contracting, the lessons here are gold.

The Power of Mentorship and Serendipity

Forrest’s path began with a chance encounter—a wing commander who took the time to mentor a high schooler. That simple act shaped his trajectory, leading him to the Air Force Academy and ultimately into a career that has influenced not just his life, but the defense community as a whole.

It’s a reminder we can’t ignore: mentorship matters. In government contracting and defense, relationships, guidance, and leadership often play as much of a role as technical skill or innovation.

From Cockpits to Contracts

What makes Forrest’s perspective unique is that he’s seen both sides of the equation. He wasn’t just a pilot—he lived the operational reality of missions, flew urgent assignments with SOCOM, and then transitioned into acquisition and advising. That real-world experience gave him a rare ability to evaluate technology not as a bureaucrat, but as someone who knows what warfighters actually need in the field.

That’s one of the biggest gaps in defense acquisition today. Too often, technology decisions are made by people far removed from operational realities. Forrest’s story proves that when operational experience informs acquisition, the results are smarter, faster, and more effective.

Why “Product–Mission Fit” Beats the Best Product

One of the key insights Forrest shared is something every startup and contractor needs to hear: in defense, the best product doesn’t always win.

Success comes down to product–mission fit. In other words, does your solution actually solve a mission need? Can it integrate into the environment, make life easier for operators, and move the needle on capability?

This is where so many companies stumble. They bring incredible technology to the table but fail to align it with what the government is truly looking for. Forrest’s advice is simple but powerful—stop selling features, start solving missions.

The Culture Gap in Acquisition

Another point Forrest hit on is the “speed gap” between Special Operations and traditional acquisition. SOCOM can move fast. They have the culture, the urgency, and the streamlined processes to field technology quickly.

But in the broader Department of Defense, things move at a crawl. The FAR, oversight requirements, certifications like FedRAMP or CMMC—all of these create friction. And yet, the need for speed has never been greater, especially with emerging threats in AI, cyber, and space.

This tension—between innovation and bureaucracy—is at the heart of defense acquisition reform. And it’s why acts like FORGE and SPEED, along with expanded use of OTAs, are so critical. They’re attempts to cut red tape and invite new players into the defense marketplace.

Bridging Silicon Valley and the Pentagon

Forrest also talked about one of his passions: connecting innovative tech companies with government buyers. Having spent time working with Silicon Valley venture capital firms, he knows the disconnect firsthand. Startups often don’t know how to navigate the defense market, while government buyers aren’t always aware of the latest commercial technologies.

That’s the gap Forrest has been helping bridge—teaching companies how to translate their solutions into government language, and helping defense leaders see where commercial innovation can give the U.S. an edge.

Where the Money’s Moving: AI, Cyber, and Space

If you’re wondering where defense dollars are flowing, Forrest made it clear: AI, cyber, and space are leading the pack. These areas are receiving heavy emphasis in defense budgets and investment portfolios.

For companies building solutions in these domains, the opportunity is enormous. On the flip side, some areas—like traditional energy or DEI initiatives—are seeing declining government interest. Understanding these shifts can make or break your contracting strategy.

The Future of Defense Innovation

Looking ahead, Forrest predicts we’re in a “calm before the storm.” With rapid advances in technology, evolving threats, and acquisition reform gathering steam, the defense sector is about to transform in a big way.

Imagine a world where companies don’t have to burn thousands of hours writing proposals and where government buyers don’t have to sift through endless paperwork. Instead, both sides could rely on transparent, honest conversations about capabilities, timelines, and funding. That’s the future Forrest envisions—and it’s one that could unlock innovation at a pace we’ve never seen before.

Key Takeaways for Contractors

Here are a few of the most practical lessons from Forrest’s journey:

• Mentorship and relationships open doors. Never underestimate the power of guidance and connection.

• Operational insight matters. If you want to succeed in defense, learn the mission inside and out.

• Product–mission fit beats flashy features. Align with real needs, not just cool tech.

• Speed is a differentiator. SOCOM shows what’s possible—use that model as inspiration.

• Follow the money. AI, cyber, and space are driving the future.

• Speak the government’s language. Translate your value into mission outcomes.

Final Thoughts

Forrest’s journey—from grocery bagger to Air Force pilot, from SOCOM to Silicon Valley, and now shaping strategy at the Pentagon—captures what’s possible when you blend experience, vision, and execution.

For those of us in government contracting, his story is both a wake-up call and an inspiration. The defense market is complex, bureaucratic, and often frustrating—but it’s also filled with opportunities for those who understand how to align innovation with mission needs.

If you’re serious about navigating this space, Forrest’s advice is clear: focus on product–mission fit, respect the process, bridge the cultural divide, and stay ahead of where the money’s moving. That’s how you don’t just win contracts—you actually make a difference.

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