Getting AI out of the POC and into production has been the defining challenge of the last three years. Brian Raymond has lived it from the inside — building infrastructure, mistiming bets, and figuring out in real time what "enterprise-ready" actually requires.

This episode covers:

• What it takes to get AI out of the demo and into production at scale
• Why senior engineering judgment matters more than headcount in the AI era
• How Unstructured crossed the Valley of Death without forking their stack — same core code base on Game Warden and in financial services
• What a decade at CIA taught Brian about paranoia as a leadership practice
• Why the dam may have finally broken on enterprise AI adoption

Brian Raymond is CEO and co-founder of unstructured.io, an AI data infrastructure company with $65M raised, 70M open source downloads, and customers spanning financial services, defense, and enterprise SaaS.

Connect with Brian:

• LinkedIn: Brian Raymond

Connect with Tyler:

• LinkedIn: Tyler Sweatt

High-level policy decrees and exciting national security headlines don't win wars. Execution does.

This week, Meagan Metzger (Founder & CEO of Dcode) joins Tyler Sweatt to pull back the curtain on the unsexy, high-stakes reality of defense acquisition reform. While leadership pushes for rapid commercial tech adoption, the "fingers-on-keyboards" workforce is left managing legacy constraints, budget shifts, and an inherent fear of administrative risk.

What’s happening on the second front:

• The critical execution gap between strategic mandates and tactical reality.
• Re-engineering the internal operating models of DoW programs to maximize authorities.
• Why commercial founders must understand the defense ecosystem better than their buyers.
• Transitioning from line-item product procurement to budgeting for mission outcomes.
• Realigning the incentives within federal labs and research communities toward true mission impact.

Connect with Meagan

• LinkedIn: Meagan Metzger

Connect with Tyler

• LinkedIn: Tyler Sweatt

At some point, every founder runs into reality.

Not just the pitch or the vision. But the part where it breaks, gets hard, and no one is coming to fix it for you.

This is where most companies are decided.

Paige Craig (Managing Founder & Partner at Outlander VC) joins guest host Sam Gray to break down how he evaluates founders in defense tech: how conviction is earned, what stands out early, and what separates the teams worth betting on.

What’s happening on the Second Front:

• What earns a first check (and what doesn’t)
• Insight, obsession, and character—and why they matter more than experience
• How strong teams handle setbacks vs. hide from them
• The reality of founder dynamics as companies grow
• Where defense tech is going—and who’s going to build it?

Connect with Paige

• LinkedIn: Paige Craig

Connect with Sam

• LinkedIn: Sam Gray 

Cyber isn’t just a compliance problem anymore.

It’s operational. It’s persistent. And it’s moving faster than the systems built to manage it.

Katherine Sutton (Assistant Secretary of War for Cyber Policy and the Principal Cyber Advisor to the Secretary of War) joins Tyler Sweatt to talk about keeping pace across policy, technology, training, experimentation, and most importantly - the people.

What’s happening on the Second Front: 

• Why cyber can’t be treated as a compliance exercise anymore
• The real bottleneck to adopting new technology (and it’s not the tech)
• How to get capability into operators’ hands faster
• Rethinking talent, training, and career paths in the cyber force
• Why incremental change won’t keep up—and what transformation actually requires

Connect with Katherine Sutton

• LinkedIn: Katherine Sutton

Connect with Tyler

• LinkedIn: Tyler Sweatt

John Price, Founder and CEO of Highground, has worked across special operations, the Senate, and private markets. Now, he’s focused on helping investors and builders understand what the government actually wants and how it buys.

He joins Tyler Sweatt to break down how demand shows up, where teams misread it, and how to identify where real programs—and real money—actually sit.

What’s happening on the Second Front

• How government demand actually shows up, and why it’s often misread
• What separates real opportunities from noise in defense markets
• How investors and operators evaluate where to place bets
• Where founders lose time (and how to move earlier in the process)
• Making the system more predictable instead of relying on luck 

Connect with John

• LinkedIn: John Price

Connect with Tyler

• LinkedIn: Tyler Sweatt

Today, Armada is opening its first Galleon Experience Center in Washington, DC.

A live environment showcasing what it actually takes to run AI at the edge—bringing together ruggedized infrastructure, cloud, and secure software deployment. With 2F Frontier as part of the stack, extending DevSecOps to disconnected, real-world environments.

And with Offset 2026 right around the corner, it felt like the right time to revisit a timely conversation from last year.

On the Offset stage, Tyler Sweatt, Pradeep Nair (Armada), Leigh Madden (Microsoft), and Korie Seville (DISA) got into:

• The gap between data and decision at the edge
• What breaks between connectivity, compute, and deployment
• Why speed to mission still comes down to authorization 

And if you want to be part of where this is going next, register for Offset 2026.

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From oil platforms to special‑ops posts, cloud infrastructures are now being deployed in environments they weren’t initially designed for. This panel explores how customized edge architectures and commercial integrations orchestrate distributed services and securely manage intermittent connectivity. All while addressing ongoing challenges in latency, interoperability, and standardization to deliver resilient, mission‑critical private clouds.

Connect with the speakers:

• Tyler Sweatt
• Pradeep Nair
• Leigh Madden
• Korie Seville

Are we even having an honest conversation about AI?

Right now the public discourse seems to bounce between two extremes: AI will save the world and AI will destroy the world.

Neither is particularly helpful.

The more interesting questions are things like: Why is there so much distrust of AI? How should governments actually think about adoption? And how can technology shorten the distance between knowledge and decision-making?

In this episode of All Quiet on the Second Front, Tyler Sweatt sits down with Igor Jablokov, Chairman & Founder of Pyron to unpack the conversation we should probably be having about AI, trust, and the future of technology.

Connect with Igor

• LinkedIn: Igor Jablokov

Connect with Tyler

• LinkedIn: Tyler Sweatt

Winning a contract isn’t the same as deploying capability.

This week, Andrew Vanderhoof (Director of DAF CLOUDworks at AFRL) joins Tyler to talk about what actually happens between “award” and “operational.”

They cover:

• Getting commercial software into classified environments
• Why OTAs and zero-dollar agreements matter
• The real weight carried by DAOs and AOs
• Scaling innovation without breaking trust
• And why the timeline is now weeks to months — not years

If you care about commercial-first actually meaning something, this one’s for you.

Connect with Andrew

• LinkedIn: Andrew Vanderhoof

Connect with Tyler

• LinkedIn: Tyler Sweatt

Government contracting moves $750B+ a year.

But the system still runs on PDFs, spreadsheets, and human bottlenecks.

This week, Derek Hoyt — CEO & Co-Founder of GovSignals — joins Tyler to talk about what happens when you aim AI directly at procurement.

They dig into:

• Why contracting shops are gutted but the dollars keep growing
• The hidden cost of B&P burn inside defense companies
• Why most new defense startups underestimate procurement
• How shrinking a 30-day cycle to a week changes everything
• And what it would take to move from risk-averse to risk-on

Connect with Derek

• LinkedIn: Derek Hoyt

Connect with Tyler

• LinkedIn: Tyler Sweatt

If we want to win the next fight, we have to outlearn first.

This week, Tyler sits down with Sir Tom Copinger-Symes, former Deputy Commander of UK's Cyber & Specialist Command (CSOC), to talk about the hard shift from infantry officer to cyber leader — and what that journey reveals about where defense is behind.

What’s happening on the second front:

• Industrial-age systems in an information-age world
• Why cyber and electronic warfare are decisive
• Why recruitment is a flow problem, not a patriotism problem
• The cognitive battlefield shaping outcomes every day
• And what dialing up risk really means

No backbone → no speed.

No speed → no advantage.

Connect with Sir Tom Copinger-Symes

• LinkedIn: Sir Tom Copinger-Symes

Connect with Tyler

• LinkedIn: Tyler Sweatt