About VA Wingman

VA Wingman is built for veterans who are trying to move forward—and don't have time to decode a broken process.

We're building the roadmap we wish existed: clear steps, plain language, and no judgment.

The Problem

The VA claims process is complex, nuanced, and intimidating. For many veterans, it hits at the worst possible time—during transition, when the priority is survival: jobs, money, family, housing.

A lot of veterans don't file, or they under-file—not because they don't deserve benefits, but because:

  • They don't know what counts
  • They don't know where to begin
  • They don't believe they'll be taken seriously
  • They feel overwhelmed and alone navigating a system full of jargon

The "done-for-you" options can cost thousands—out of reach for many separating enlisted families

So benefits get delayed, missed, or avoided entirely—often for years.

The Solution

VA Wingman is TurboTax-style guidance for VA claims, with the veteran in control.

The core of the product is what we call VA Claims TTPs (tactics, techniques, and procedures): bite-sized condition guides that break the process into plain steps:

  • What counts (plain language + references)
  • What the VA evaluates and what actually matters
  • Evidence checklists + templates
  • How to describe functional impact honestly
  • A next-step checklist you can follow without guessing

We're not here to replace VSOs or attorneys. We're here to help veterans start confidently, DIY the right way first, and know when it's time to escalate.

Why We're Building This

VA Wingman started with a simple observation: a strong claim shouldn't require extreme tenacity.

Dave went through separation with a family and real pressure—trying to figure out civilian life while also navigating injuries and paperwork that felt designed to confuse. He learned the system the hard way, then realized something important:

If the process can be learned, it can be taught—and it can be made to feel doable.

That's what VA Wingman is: the "wingman" most veterans never get.

Our Team

Dave Hunt — Cofounder

Combat veteran. Separated after years of service and firsthand experience with how overwhelming the claims process can be. Building VA Wingman so other veterans don't have to start from zero.

Devon Garbalosa — Cofounder

Civilian ally and builder, passionate about veteran outcomes and making sure this gets shipped—not someday, but soon.

We're starting with pilots through TAP at JBMDL, where Dave went through transition himself.

Who It's For

  • Separating service members (0–180 days)
  • Veterans who never filed because they didn't document much
  • Anyone navigating the VA system who needs clarity and confidence

Get In Touch

We're raising $250k for tranche one to build a pilot-ready MVP, publish the first 30 VA Claims TTPs (condition guides), and run a TAP pilot with 25–50 separating service members.

If you're interested in being a Founding Sponsor—or you know someone who funds veteran outcomes—we'd love to connect.

Contact: [email protected]