Lisa Sutton Gunderson has never worn a uniform. But as a General Partner at The Veteran Fund — a seed-stage VC backing veteran-led critical technology companies in defense tech, autonomy, space, and AI — she might have more conviction about what veterans are capable of than most people who have. 

We get into why the "step down and start over" script handed to transitioning veterans is wrong, what an elite operator looks like when they bet on themselves, why her fund pairs veteran operators with technical co-founders, and why treating veterans as a charity case instead of a competitive advantage gets the whole thing backwards. 

The Veteran Fund: https://www.veteran.fund
Lisa on LinkedIn: https://www.linkedin.com/in/lisasongsutton 

A Paralax production. 
© 2026 Paralax Media. All rights reserved. 

The veteran hiring system isn't broken because nobody cares. It's broken by design. 

Brian Nichols has sat on the other side of the table for his entire career — as a Navy recruiter, at Wounded Warrior Project, running talent acquisition for some of the largest employers in the country. Over 25,000 placements. More than 5,000 veterans. 

He knows exactly how the machine works... and why it keeps failing you. 

A Rompus Media production. 
© 2026 Rompus LLC. All rights reserved. 

Keith Dupont left the Army after a strong run as a top-rated company commander and battalion operations officer. What followed was a compressed transition, 100 job applications, and... silence. 

We talk through what that actually felt like, where the process broke down, and what ultimately helped Keith find traction. This is a grounded look at transition from someone who went through it in real time. 

A Rompus Media production. 

© 2026 Rompus LLC. All rights reserved. 

Kyle Packard and I get into what actually creates leverage after service, what people get wrong about money and planning, and why a lot of vets are in a much stronger position than they realize. 

Kyle — Army strategist, CFP®, and entrepreneur — breaks down what actually matters: pension, optionality, business ownership, and why blindly following advice will box you in. 

A Rompus Media production. 

© 2026 Rompus LLC. All rights reserved.

The wrong map. The wrong assumptions. The wrong expectations. 

In this Field Notes episode we move from diagnosing the environment to owning your position inside it: speed, risk, timing, tradeoffs, and the decisions that only belong to you. 

If the terrain feels disorienting, it’s because you were handed the wrong map. Start where you’re actually standing. 

A Rompus Media production. 
© 2026 Rompus LLC. All rights reserved.

Endless advice. Endless engagement. No accountability... 

In this Field Notes episode, we examine the military transition “industry”: the attention loops, the placement pipelines, and the incentives, money, and grift that shape what veterans are told. 

Look closely at who the military transition industry actually serves. 

A Rompus Media production. 
© 2026 Rompus LLC. All rights reserved.

A senior title. A respected logo. Proximity to power. But the scope, authority, and compensation don’t match what you’ve already demonstrated you can do. 

In this Field Notes episode, we unpack how prestige can mask a step down, why veterans keep getting encouraged to “take the step-down role,” and why that trade almost never corrects itself later. 

A Rompus Media production. 
© 2026 Rompus LLC. All rights reserved.

We’ve been handed a story about the military-to-civilian transition... one that sounds clean, seamless, and inevitable. It rarely is. 

In this first Field Notes episode, we unpack the myth of the “perfect landing,” why so many capable veterans feel lost, and how expectation quietly turns into frustration. 

If your transition hasn’t gone according to plan, you’re not broken. You’re just operating inside a narrative that doesn’t match reality. 

A Rompus Media production. 
© 2026 Rompus LLC. All rights reserved.