Matt Samson, CPWA®, MBA

Military Retirement, Airline Pilot, & Veteran Business Owner Financial Planning

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ILS Financial Matt Samson, CPWA®, MBA

Omaha, NE

Serving Clients Nationwide

Military Retirement, Airline Pilot, & Veteran Business Owner Financial Planning

(402)204-0230

Website

Areas of Focus

Estate Planning
High Net Worth
Investment Management
Retirement Planning
Tax-Smart Accumulation Planning
Tax-Smart Distribution Planning

About Matt Samson, CPWA®, MBA

Matt Samson, CPWA®, MBA, is the President of ILS Financial, a Nebraska-registered Registered Investment Adviser based in Omaha. He specializes in helping retiring military officers, airline pilots, and veteran business owners navigate high-impact financial decisions in the correct order.

His practice centers on a simple but often overlooked principle: major financial outcomes are driven less by product selection and more by the sequence in which irreversible decisions are made.

Matt works with clients facing complex intersections of:
Military pensions and SBP elections
TSP rollover timing
VA disability integration
Airline 401(k) coordination and employer contributions
Company stock concentration risk
Tax-aware retirement income sequencing

As a former Marine Corps F/A-18 aviator, Matt understands both the cultural and structural realities of military transition and aviation careers. His approach reflects that background — disciplined, analytical, and decision-focused.

Rather than beginning with investment allocation, Matt begins with decision architecture:
Identify irreversible decisions
Clarify tradeoffs
Sequence major elections properly
Optimize portfolio structure afterward

This framework is particularly important for senior officers and airline pilots, where pensions, benefits, tax exposure, and career risk interact in ways that generic planning models often miss.

Professional Designations

Certified Private Wealth Advisor (CPWA)
Master of Business Administration (MBA)

Primary Location

10050 Regency Cir, Suite 533 Omaha, NE 68114

Meeting Options

Video Conference
In-Person
Phone

Book Intro Call

Compensation Methods

Commissions
Hourly Rate
One-time Financial Plan
Percentage of Assets Managed
Subscription

What to expect in the first meeting

Click the 'Book Intro Call' button above to schedule a free Fit Call. We'll start our journey with a brief, yet meaningful, conversation. Through a Fit Call, we aim to learn more about you, your aspirations, and whether our services can provide genuine value. This initial connection sets the foundation for our partnership and ensures that we are aligned in pursuing your financial well-being. I look forward to speaking with you.

Offers Investment Management

Yes

About ILS Financial

ILS Financial is a Nebraska-registered Registered Investment Adviser based in Omaha, serving clients nationally. The firm specializes in retirement decision planning for senior military officers, airline pilots, and veteran business owners navigating complex financial transitions.
At ILS Financial, we believe financial outcomes are driven less by product selection and more by the order in which major decisions are made. Our planning process emphasizes disciplined decision sequencing — identifying irreversible elections first, clarifying tradeoffs, and structuring retirement income before optimizing portfolio construction.
Many of our clients operate in multiple financial systems simultaneously — military pensions and SBP elections, TSP and civilian retirement accounts, VA disability benefits, airline compensation structures, and concentrated employer equity. These systems often intersect in ways that generic planning models fail to address.
Our role is to bring structure to those intersections.
Rather than beginning with asset allocation, we begin with decision architecture:
• Identify high-impact and irreversible decisions
• Evaluate tax and income implications
• Sequence elections appropriately
• Align investments with the finalized structure
This framework is particularly relevant for military retirees and airline professionals, where pension timing, benefit integration, and career risk can materially affect long-term outcomes.
ILS Financial operates as a fiduciary advisory firm, providing financial planning and investment management services tailored to clients with complex retirement and transition considerations.

If you are navigating a military transition, airline career complexity, or high-impact retirement decisions, I welcome a conversation.
Call (402) 204-0230 or email matt.samson@ilsfinancial.com to schedule an introductory discussion. We can review your current structure, identify key decision points, and determine whether a disciplined sequencing approach makes sense for your situation.

Education

University of Nebraska-Lincoln, Bachelor of Science (B.S.)|University of Nebraska at Omaha, Master of Business Administration (MBA)| Yale School of Management, Certificate in Wealth Management Theory and Practice

Hobbies and Interests

Baseball
Church
Family
Football
Sports
Traveling

SEC Lookup

View Disclosure

Who We Serve

Airline Pilots
Baby Boomers
Business Owners
Corporate Executives
Families
Government Employees
Military
Veterans

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