All Quiet on the Second Front

Buying satellite imagery used to take a year of contract negotiations, and the images still arrived as PDFs. SkyFi launched in 2023 to simplify the process and had users in 180 countries within two weeks.

By the time government customers came calling, the product was already battle-tested by commercial users, ready for a market that rarely gives second chances.

This week, Luke Fischer, a 20-year Army veteran, former special ops aviator, and now SkyFi co-founder, joins Sam Gray to share what he's learned building a dual-use company commercial-first.

• Leveraging your commercial base to show up ready for the gov
• Why a continuing resolution can make a dual-use company more attractive to investors
• What happens when warfighters, not leadership, do the selling
• Staying competitive with AI as a small company

Connect with Luke

• LinkedIn: Luke Fischer

Connect with Sam 

• LinkedIn: Sam Gray

Roughly $100 billion a year goes into federal IT, and by GAO’s count about 80% of it goes to maintaining old, complex legacy code bases. As AI speeds up everything built around them, those code bases become the thing the whole enterprise waits on. Jake Sortor ran into this himself as an intelligence officer in Iraq, trying to get a Python script he'd written tested on a secure network. He leads public sector at Blitzy now, and his argument is that AI is the only thing that attacks a backlog this size — with humans still making every decision that matters.

What's happening on the second front:

• Why maintaining legacy code, not model capability, is the ceiling on government software speed
• What “human in the lead” actually looks like when 80–90% of the development lifecycle is automated
• The case that automation turns developer work into judgment — architecture, deployment, configuration — rather than eliminating it
• Why state and local government may be the most underserved and most transferable market in modernization
• What Jake learned teaching himself Python downrange in Iraq to fix a clunky Excel workflow, and the heat he took for it

Jake Sortor is a former Air Force intelligence officer who taught economics at the Air Force Academy, went on to a JD/MBA and a year in corporate law, and now leads public sector at Blitzy while continuing to serve in the reserves.

Connect with Jake

• LinkedIn: Jake Sortor

Connect with Tyler

• LinkedIn: Tyler Sweatt

In 2020, telling people that organized actors were using bots to shape what the public believes got you called a conspiracy theorist. 

The one audience that didn't need convincing was the national security community, which had been thinking about the battle for perception long before it had a commercial market.

Now, the problem has a name — cognitive warfare — and it has changed shape. The target is no longer the information environment. It is cognition itself, and AI has collapsed the cost of attacking it. Blackbird CEO Wasim Khaled returns to All Quiet to walk through what narrative attacks look like now, who is actually getting hit, and why monitoring the problem was never the mission.

What’s happening on the Second Front: 

• Why “misinformation” and fact-checking became the wrong frame, and what narrative intelligence replaced them with
• What AI did to the economics of a narrative attack — from troll farms to autonomous agents, and from “where are the bots?” to “where are the people?”
• Who gets targeted now: members of Congress, CEOs, even shareholder votes — not just the credulous
• Why most platforms stop between observe and orient, and what it takes to close the loop through decide and act
• Prediction that isn’t fortune-telling, it’s reducing the number of futures that can surprise you

Wasim Khaled is co-founder and CEO of Blackbird.AI, whose Constellation platform helped define the narrative intelligence category; a computer scientist by training, he built and scaled an Inc. 500 company before turning to information warfare.

Connect with Wasim

• LinkedIn: Wasim Khaled

Connect with Tyler

• LinkedIn: Tyler Sweatt

Twenty years ago, a young logistics lieutenant solved an impossible field problem with a Franklin Planner, a satellite phone, and a contact who happened to be at his desk. It worked — but it ran on luck. Bill Pessin has spent his career since making sure the mission never has to. He joins Tyler Sweatt to trace the line from Army logistics to leading Salesforce’s Missionforce, and why acceleration, not just speed, is the point.

What's happening on the Second Front:

• How a satellite phone and a Franklin Planner solved an impossible field problem — and why depending on luck is a system failure
• Why Salesforce is the “central nervous system” of the mission enterprise, from HUMINT to workflow
• How Missionforce was born from a single dinner between Marc Benioff and a combatant commander
• What “acceleration” really means when moving faster through the mission is the goal, not the metric
• The one piece of government friction he’d fix first if he had a magic wand

Bill Pessin is SVP of Missionforce at Salesforce and a U.S. Army veteran who has led the company’s national security business since 2014.

• Connect with Bill: https://www.linkedin.com/in/billpessin/
• Connect with Tyler: https://www.linkedin.com/in/tylersweatt

Every veteran gets the same advice on the way out: "your service will speak for itself." It won't. In this episode, Tyler Sweatt sits down with Kyle Eberly, Wyatt Frasier, and Max Cormier, the leadership team behind Sitreps — the recruiting firm that's become the go-to clearinghouse for veteran talent in defense tech and private equity — to give it to transitioning service members straight.

They cover:

• Why civilian employers care about value and dependability, not your combat record — and how to lead with that
• The difference between "signal" and "human capital," and why vets almost always need the former
• Whether an MBA is still worth it (and why "getting an MBA on YouTube" is a trap)
• The negotiation and entitlement mistakes that cost people offers at the one-yard line

Connect with the Sitreps Team:

• Wyatt Frasier, CEO
• Kyle Eberly, Chairman and CTO
• Max Cormier, COO

Connect with Tyler:

• LinkedIn: Tyler Sweatt

A foreign partner's payment has sat in a U.S. government account for nearly a year. The order still hasn't shipped. It's stuck in contracting. That kind of friction is exactly what Church Hutton, Chief Growth Officer at AV, has spent his career navigating: from Senate Armed Services and Appropriations staff, to Army Reserve officer, to leading growth at a company that just doubled in size by acquiring Blue Halo.

Tyler and Church dig into:

• Why "cost per effect" is broken — the U.S. is shooting down $20K threats with million-dollar interceptors
• Why laser weapon systems are finally moving from prototype to production after decades of false starts
• The historical parallel between the Army's interwar cavalry branch and today's Pentagon modernization fights

__________

Church Hutton has spent over two decades moving between Capitol Hill, uniformed service, and defense industry leadership, most recently steering growth at AV through its transformation into a full-spectrum autonomous systems company.

Connect with Church

• LinkedIn: Church Hutton

Connect with Tyler

• LinkedIn: Tyler Sweatt

Breaking into aviation as a startup means years of quiet, brutal work with nothing to show for it publicly. Zach Shore calls it startups on hard mode: the pain is real, but the moat is massive.

Now Hermeus is the fastest company in history from founding to supersonic flight, and its newly minted CEO sits down with Tyler to explain how a small team out-built a 75-year-old industry.

• "Own the outcome, not the action" — the whole job of leadership at scale
• Why adding sales headcount early creates crosscurrents, not coverage
• 74 days from build stand to weight on wheels, and why building more planes makes you faster
• Keeping your mouth shut as go-to-market strategy in a zero-sum budget world

Zach Shore is the CEO of Hermeus, a former Marine SIGINT officer and Anduril early employee who led the Lattice program before joining Hermeus to build its go-to-market motion from scratch.

Connect with Zach

• LinkedIn: Zach Shore

Connect with Tyler 

• LinkedIn: Tyler Sweatt

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