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From Special Ops to the Pentagon: Forrest Underwood on AI, Startups, and the Future of Defense Contracting
Forrest Underwood’s career spans flying MC-130Js for Special Operations, standing up new squadrons overseas, embedding with SOCOM on urgent missions, working with Silicon Valley venture capital firms, and now serving as Chief of Joint Investment Strategies at the Office of the Secretary of Defense and the CEO of Evergreen Industries
In this conversation, Forrest explains:
How AI, cyber, and space tech companies can break into defense contracting.
Why “product–mission fit” is the key to winning contracts without wasting resources.
The cultural speed gap between Special Operations and traditional acquisition.
How the Forged Act, Speed Act, OTAs, and acquisition reform will change the landscape.
Why the best product doesn’t always win — and how to fix it.
If you’re a founder, tech leader, or government contracting professional, this episode is packed with actionable insights to help you navigate — and win in — the defense market.
Connect with Forrest on LinkedIn: https://www.linkedin.com/in/forrestunderwood/
Timestamps / Chapters
00:00 – The calm before the storm in defense acquisitions
00:40 – AI writing proposals for AI: The growing noise problem
01:15 – Special Ops speed: Delivering tech in under 24 hours
02:00 – Forrest Underwood: From pilot to defense tech strategist
03:00 – The grocery store encounter that launched an Air Force career
04:00 – Air Force Academy prep school: Building future officers
05:00 – Pilot training pipeline and aircraft assignments
07:00 – C-130J missions in Europe and Africa
09:00 – Standing up an MC-130J squadron in Okinawa
11:00 – Transitioning to joint staff roles in Stuttgart
14:00 – SOCOM immersion in Silicon Valley venture capital
15:00 – Working with VC firms on AI, cyber, and space tech
17:00 – The cultural speed gap in acquisitions
19:00 – Overnight integration of mission-critical tech
22:00 – Moving into acquisitions leadership at OSD
23:00 – Managing $200B in annual defense investments
24:00 – Founding Evergreen Industries and product–mission fit
28:00 – Navigating the valley of death in defense innovation
29:00 – OTAs, SBIRs, DIU, and accelerating acquisition
30:00 – Forged Act, Speed Act, and acquisition reform
32:00 – Why quality beats volume in proposals
34:00 – Non-traditionals vs. primes in the new acquisition era
36:00 – Cybersecurity compliance and small business challenges
39:00 – Why the best product doesn’t always win
40:00 – Mapping capabilities to joint warfighting needs
42:00 – Accelerating serious companies into DOD contracts
45:00 – Sell it first, build it second in defense tech
46:00 – Validating demand before developing solutions
47:00 – Discovery-driven selling in the DOD
49:00 – Understanding frustrations on both sides of the process
50:00 – How acquisitions officers evaluate new tech
53:00 – Where defense tech funding is headed
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