We help retiring military veterans, airline pilots, and veteran business owners make the right financial decisions in the right order during high-stakes transitions.

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Who We Serve

Specialized planning for specific transitions.

Financial planning for senior military officers

Senior Military Officers

Pension elections, SBP structure, TSP, second-career income coordination, and irreversible decision sequencing.

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Military pilots transitioning to the airlines

Military-to-Airline Transitions

Pension sequencing, SBP elections, TSP, and airline compensation structure through the transition year and beyond.

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Financial planning for veteran airline pilots

Airline Pilots

Career fragility modeling, retirement plan stack integration, and income planning through peak earning years.

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Financial planning for fractional aviation pilots

Fractional Aviators

Variable income planning, gateway domicile, 401(k) contract specifics, and fractional career transition strategy.

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How We Help

Structure before optimization.

Transition-Focused Financial Planning
Guidance for high-stakes career, retirement, and liquidity transitions — with an emphasis on decision sequencing and coordination.
Investment Strategy & Portfolio Structure
Thoughtful portfolio construction and risk management aligned to long-term objectives — not short-term market noise.
Retirement & Pension Decision Planning
Analysis and coordination of military and civilian retirement decisions, including SBP and income replacement considerations.
Tax-Aware Planning & Coordination
Integrated tax planning designed to reduce friction across income, investments, and major life events.
Military Benefit Integration
Strategic use of TSP, VA disability, and related benefits within the broader financial picture — not in isolation.

We Are ILS Financial

Clarity for High-Stakes Financial Transitions

At ILS Financial, we work with retiring military veterans, airline pilots, and veteran business owners navigating complex, high-stakes financial transitions.

Our approach focuses on decision sequencing — ensuring critical choices around retirement, taxes, investments, and risk are made in the right order before they become difficult or impossible to undo. Rather than leading with products or performance, we prioritize clarity, coordination, and long-term confidence in direction.

We understand the unique complexity these transitions create and help clients move forward with discipline, intention, and alignment.

Matt Samson, MBA, CPWA® — ILS Financial
MBA CPWA® Marine Aviator

Matt Samson, MBA, CPWA®

Founder, ILS Financial

High-stakes financial transitions often feel manageable—until multiple decisions begin to converge at once.

I founded ILS Financial to help retiring military veterans, airline pilots, and veteran business owners navigate these moments with clarity and discipline. My work focuses on decision sequencing—ensuring critical choices around retirement, taxes, investments, and risk are made in the right order before they become difficult or impossible to reverse.

Before entering financial services, I spent over ten years on active duty as a Marine aviator — flying the F/A-18 Hornet before transitioning to UAS and Space Operations. That background in disciplined decision-making, risk management, and preparation under pressure continues to shape how I approach financial planning today.

I transitioned into financial planning in 2015 and founded ILS Financial LLC in 2020. I continue to serve in the Marine Corps Reserves, bringing over twenty-three years of combined active and reserve experience to the work.

As a fiduciary and CERTIFIED PRIVATE WEALTH ADVISOR® professional, I help clients coordinate complex financial decisions across multiple domains — not by leading with products or promises, but by creating clarity, alignment, and confidence in direction during pivotal transitions.

Additional Resources

Further reading by audience.

We've put together some additional resources we hope you may find helpful.

The Briefing Room
The Briefing Room Explore
Senior Military Officer Resources
Senior Military Officer Resources Explore
Military to Airline Transitions
Military to Airline Transitions Explore
Commercial Pilot Resources
Commercial Pilot Resources Explore
Fractional Aviator Resources
Fractional Aviator Resources Explore

Financial transitions don't require urgency — they require clarity.

If you're approaching a significant decision or transition and want confidence that the most important choices are being made in the right order, a fit meeting can help determine whether working together makes sense.

Book A Fit Meeting Today

How ILS Supports Business Owners in Transition

Business ownership creates opportunity — and complexity. Liquidity events, reinvestment decisions, tax exposure, and personal financial planning often converge at the same time.

At ILS Financial, we help veteran business owners navigate these moments by focusing on decision sequencing and coordination across personal and business finances. Our role is to ensure critical choices are made intentionally and in the right order before implementation begins.

This approach helps business owners move forward with confidence, clarity, and alignment — particularly when decisions carry long-term consequences.

Find Out How