Forrest Underwood: The Future of Defense Contracting

14/08/2025 55 min

Listen "Forrest Underwood: The Future of Defense Contracting"

Episode Synopsis

In the GovClose Certification Program, our students learn the government contracting skills to:Start their own consulting business that can earn up to $400k as a “solopreneur” advising businesses that sell to the government.Land high-paying sales executive jobs with companies selling to the government.From Special Ops to the Pentagon: Forrest Underwood on AI, Startups, and the Future of Defense ContractingForrest 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 IndustriesIn 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 / Chapters00:00 – The calm before the storm in defense acquisitions00:40 – AI writing proposals for AI: The growing noise problem01:15 – Special Ops speed: Delivering tech in under 24 hours02:00 – Forrest Underwood: From pilot to defense tech strategist03:00 – The grocery store encounter that launched an Air Force career04:00 – Air Force Academy prep school: Building future officers05:00 – Pilot training pipeline and aircraft assignments07:00 – C-130J missions in Europe and Africa09:00 – Standing up an MC-130J squadron in Okinawa11:00 – Transitioning to joint staff roles in Stuttgart14:00 – SOCOM immersion in Silicon Valley venture capital15:00 – Working with VC firms on AI, cyber, and space tech17:00 – The cultural speed gap in acquisitions19:00 – Overnight integration of mission-critical tech22:00 – Moving into acquisitions leadership at OSD23:00 – Managing $200B in annual defense investments24:00 – Founding Evergreen Industries and product–mission fit28:00 – Navigating the valley of death in defense innovation29:00 – OTAs, SBIRs, DIU, and accelerating acquisition30:00 – Forged Act, Speed Act, and acquisition reform32:00 – Why quality beats volume in proposals34:00 – Non-traditionals vs. primes in the new acquisition era36:00 – Cybersecurity compliance and small business challenges39:00 – Why the best product doesn’t always win40:00 – Mapping capabilities to joint warfighting needs42:00 – Accelerating serious companies into DOD contracts45:00 – Sell it first, build it second in defense tech46:00 – Validating demand before developing solutions47:00 – Discovery-driven selling in the DOD49:00 – Understanding frustrations on both sides of the process50:00 – How acquisitions officers evaluate new tech53:00 – Where defense tech funding is headedJOIN the GovClose CommunityFollow me on LinkedIn for our free GovClose Newsletter and real-world GovCon insights👉 https://www.linkedin.com/in/govclose/