Winged Wealth Management and Financial Planning

06/15/2026

We tend to treat financial literacy like a class you take later in life—something you pick up once you have a “real job,” a mortgage, or a growing investment account.

But that’s backwards.

By the time most people start thinking seriously about money, they’ve already formed the habits that will drive the majority of their financial outcomes. Spending patterns, risk tolerance, savings behavior, even emotional reactions to money—those are built early, often long before someone understands what a Roth IRA is.

Financial literacy isn’t about memorizing terms. It’s about building decision-making instincts over time.

And like anything else that matters, the earlier you start, the better the outcome.

When Should Financial Literacy Start?
Short answer: Earlier than most people think.
Long answer: It should evolve in stages.

Early Childhood (Ages 5–10): Build Awareness

At this stage, kids don’t need to understand compound interest or tax brackets. What they can understand is:
• Money is earned
• Money is finite
• Choices have trade-offs

Simple techniques work best:
• Give small amounts of money tied to chores or responsibilities
• Let them make spending decisions (and mistakes)
• Introduce the idea of saving vs spending

The goal here isn’t optimization—it’s exposure.

Pre-Teen to Teen (Ages 11–18): Build Habits

This is where things start to stick.
They’re old enough to understand:
• Delayed gratification
• Basic budgeting
• The difference between wants and needs

Practical steps:
• Open a checking or savings account
• Introduce a debit card with guardrails
• Have them track spending (even loosely)
• Encourage saving for larger purchases instead of instant buying

This is also the perfect time to introduce:
• The basics of investing
• How debt works (before it’s offered)

The biggest win here is helping them connect today’s decisions with future consequences.

Early Adulthood (18–30): Build Systems

This is where most people finally engage with money—and where mistakes get expensive.

Now the focus shifts to:
• Creating a basic financial plan
• Understanding taxes, benefits, and retirement accounts
• Avoiding high-interest debt traps
• Building an emergency fund

At this stage, financial literacy becomes less about knowledge and more about ex*****on.

The Core Principles That Actually Matter

Financial literacy can feel overwhelming because there’s so much information. But most of it boils down to a few foundational ideas.

1. Spend Less Than You Earn
Simple. Not easy.
This is the foundation everything else sits on. Without it, no amount of investing knowledge will save you.

2. Time Is More Powerful Than Timing
You don’t need to be a market expert. You need consistency.
The earlier money is invested, the more time it has to grow. That’s where the real advantage comes from—not picking the perfect stock.

3. Avoid High-Interest Debt
Not all debt is bad, but high-interest consumer debt is one of the fastest ways to stall financial progress.
Understanding how interest works—especially against you—is critical.

4. Simplicity Wins
Most successful financial plans are boring:
• Save consistently
• Invest in diversified, low-cost funds
• Avoid unnecessary complexity

Complications often introduce cost, and cost reduces outcomes.

5. Behavior Beats Knowledge
You can know everything and still fail financially if your behavior doesn’t align.
Consistency, discipline, and emotional control matter more than intelligence in this space.

Techniques That Actually Work
There’s no shortage of financial advice, but only a handful of techniques consistently deliver results.

Make It Visual
For kids and adults alike, abstract concepts are hard to grasp.
• Use jars or buckets for spending, saving, and giving
• Show account balances growing over time
• Use simple charts to demonstrate progress
Seeing money move changes behavior.

Automate Good Decisions
The less you rely on willpower, the better.
• Automatic transfers to savings
• Automatic contributions to retirement accounts
• Auto-pay for bills to avoid late fees
Automation turns good intentions into consistent action.

Let Mistakes Happen (Early and Small)
One of the best teachers is experience.
• Overspending a small amount early is far better than learning that lesson later with a credit card
• Making a bad purchase decision teaches more than a lecture ever will
The key is keeping the stakes manageable.

Talk About Money Openly
For many families, money is either stressful or taboo—often both.
That silence creates confusion.
Instead:
• Talk through decisions
• Explain trade-offs
• Share reasoning, not just outcomes
Financial literacy improves dramatically when money becomes a normal topic.

Connect Money to Goals
Saving “just to save” doesn’t stick.
Saving for:
• A trip
• A car
• Financial independence
• Flexibility in life
That creates motivation.
Money is a tool. People engage with it more when they understand what it’s for.

Common Mistakes to Avoid
Some financial missteps are more about mindset than math—and they can undo years of progress.

❌ Waiting Too Long to Start - The biggest mistake isn’t doing it wrong—it’s not doing it at all. Delaying saving or investing even a few years can have a massive long-term impact.

❌ Overcomplicating Everything - You don’t need complex strategies, constant market updates, or the “perfect” plan. You need a good plan that you stick to.

❌ Learning Only from Social Media - There’s a lot of good information out there—and a lot of noise. Be cautious of “Get rich quick” strategies, overly aggressive investing advice, and content designed more for clicks than outcomes.

❌ Ignoring Taxes and Fees - Small percentages matter more than people think. High fees reduce long-term growth, and poor tax decisions can cost thousands over time. These are quiet drags on performance.

❌ Not Adjusting Over Time - What works at 25 won’t necessarily work at 45. Financial literacy isn’t a one-time event—it’s an ongoing process. Plans should evolve as life changes.

The Bigger Picture

Financial literacy isn’t about turning everyone into an expert. It’s about giving people enough understanding to make informed decisions, avoid costly mistakes, and build a life with more options and less stress. It’s not just about money, it’s about control, flexibility, and peace of mind. And the reality is, most people don’t need to do anything extraordinary to succeed financially. They just need to start earlier, stay consistent, and avoid the major pitfalls.
If there’s one takeaway, it’s this: Financial literacy isn’t a single lesson—it’s a lifelong skill built through small, consistent actions.

Fight’s On!

06/08/2026

Monday Money: Why Veterans Should Embrace The VA Disability Process

For many veterans, filing for a VA disability rating sits somewhere between “I’ll get to it later” and “that’s not really for me.” There’s a quiet resistance to it—sometimes out of pride, sometimes out of discomfort, and often out of a belief that it’s somehow gaming the system.

It’s not.

In fact, for separating or retiring service members, going through the VA disability evaluation process is mandatory. The system is going to evaluate you whether you lean into it or not. The real decision isn’t whether to participate—it’s whether you’re going to approach it honestly and intentionally, or rush through it and potentially leave meaningful benefits on the table.

And for pilots in particular, this conversation hits a little differently.

The Pilot Mentality: “Don’t Go DNIF”:

If you’ve spent time in aviation, you already know the culture.

Aches and pains?
“Just part of the job.”

Something bothering you physically?
“Give it a day.”

There’s always that underlying pressure—spoken or unspoken—to avoid going DNIF (Duties Not Including Flying). Because going DNIF means stepping out of the cockpit, impacting the mission, and sometimes feeling like you’re letting the team down.

So what happens?

You push through.
You “walk it off.”
You rub some dirt on it and keep flying.

That mindset builds great operators. It does not build a great paper trail for your long-term health.

The Problem With Toughing It Out:

What makes you effective in uniform can work against you later.

When it comes time to go through the VA disability process, the system isn’t evaluating how tough you were—it’s evaluating what impact your service had on your body over time.

If you spent years:

Not reporting issues
Minimizing symptoms
Avoiding medical documentation

Then you’re essentially asking the VA to connect dots that were never clearly recorded.

And that’s where many veterans unintentionally shortchange themselves.

This Isn’t About Gaming the System:

There’s a persistent misconception that filing for VA disability—or being thorough in the process—is somehow taking advantage of the system.

It’s not.

The VA disability framework exists to:

Recognize service-connected wear and tear
Provide compensation for long-term impact
Support veterans as those conditions evolve over time

Being honest about your condition isn’t exaggeration.
It’s not “working the system.”

It’s simply participating in the system the way it was designed to work.

Why the Rating Matters More Than You Think:

A VA disability rating isn’t just a number—it’s a gateway to a range of benefits that can meaningfully impact your financial life and your family’s future.

That includes monthly, tax-free compensation, access to healthcare, and eligibility for additional federal and state-level programs. But beyond that, it creates something even more important: a documented record of your conditions.

Because here’s the reality—what feels manageable at 30 or 35 often doesn’t stay that way.

The Value of a 90% Rating (Especially in Virginia):

For veterans living in Virginia, even a 90% disability rating can provide a strong financial and support foundation.

The monthly compensation at that level is substantial and, importantly, tax-free. That alone can create breathing room in a financial plan—whether it’s offsetting living expenses, reducing reliance on earned income, or allowing for more flexibility in career decisions.

It also expands access to VA healthcare, often reducing or eliminating out-of-pocket costs for many services. For someone who has spent years pushing through physical strain, that access becomes increasingly valuable over time.

And then there are the family implications.

The Overlooked Benefit: Chapter 35:

If a veteran is rated at a level that qualifies as Permanent & Total, their dependents may be eligible for Chapter 35 DEA benefits.

This is one of the most underutilized and under-discussed benefits available.

It provides education assistance for spouses and children, including monthly stipends that can be used for college, trade schools, and certification programs. Over time, this can represent tens of thousands of dollars in value, directly supporting your family’s future.

It’s not just about your rating—it’s about what that rating unlocks for the people around you.

The Importance of Being Up Front:

When you go through your VA exams and documentation, there’s a natural tendency—especially among pilots and high-performers—to downplay things.

You might think:

“It’s not that bad”
“I can still function”
“Others have it worse”

All of that may be true. But it’s not what the VA is measuring.

They’re looking at:

Frequency of symptoms
Severity
Impact on daily life

If you minimize those factors, your rating will reflect that. And once that rating is set, correcting it later can be a much steeper uphill climb.

Being up front doesn’t mean exaggerating—it means accurately describing reality, not the version of it you’ve learned to tolerate.

Think About Your Future Self:

The version of you making this decision today is likely still capable, still pushing, still adapting.

But the VA process isn’t about just today—it’s about the next 10, 20, or 30 years.

That knee that aches after long flights.
That back that tightens up after sitting in the cockpit.
That hearing that’s not quite what it used to be.

Those things tend to compound, not disappear.

And if they’re not documented now, connecting them back to your service later becomes significantly harder.

Embrace the Process:

You don’t have to love the VA process. Most people don’t.

But it’s worth reframing how you think about it.

This isn’t:

A handout
A loophole
Or a system to game

It’s part of your transition.
It’s part of closing the loop on your service.
It’s part of taking care of your future.

And most importantly—it’s something you’ve already earned.

Final Thought:

For years, you showed up, did the job, and pushed through whatever came your way—often without complaint.

But this is one area where that same mindset can cost you.

So don’t rush it. Don’t minimize it. And don’t treat it like an afterthought.

Go through the process. Be honest. Document everything.

Because the goal isn’t to get the highest rating possible.
The goal is to get the right rating, based on the reality of what your service required of you.

And that starts with telling the full story—even the parts you’ve been trained to ignore.

06/01/2026

Monday Money: I Know How Much You Spend. Do You?

Of the hundreds of families I’ve served, there is a 99.99% common trait and my family shares it too: we don’t know how much we spend. As virtuous as Davey Ramsey’s “plan and track” every nickel (since pennies aren’t a thing) advice is, it’s tedious at best. If we don’t know what we spend, it’s really hard to plan for the future, especially when the paycheck switch flips to the OFF mode.

Why We Don’t Track Spending:

Even with slick tools like Monarch Money and other financial aggregators, you must review, categorize, process, and acknowledge every electronic transaction in a day/week/month/year. Most families have hundreds of transactions per month, and many transactions span multiple categories. Even if you’re a bookkeeper, you’d be getting paid to do this for someone else. Where’s the compensation for your time, energy, and attention when you track spending in your own home?

Reviewing spending induces lots of emotions, and few of them are “spender’s joy.” It’s all but impossible not to reflect on a month’s worth of spending without thinking things like:

“Where did it all go?”

“Did we really (need to) spend so much at Target/Amazon/Costco?”
“When did things get so expensive?”

“We probably need to start talking before we do some of this spending … and that’s probably an argument…”

Unless we’re one of those rare types who just likes having a tidy profit and loss statement for the household, tracking spending ranks right up there with cleaning gutters and picking weeds.

Here’s What You Spend:

There is actually a really simple way to know what you spend, and it’s how I know what you spend.

Gross Income minus taxes minus savings, divided by 12.

In most cases, this really is the number. But let’s slice this elephant into some mouth-fitting chunks:

1. What was your gross income on your last tax return? Add any VA disability pay and, if you received any significant gifts, those amounts too.

2. What was your tax bill? This one is a little trickier because your 1040 tax form doesn’t show Social Security and Medicare taxes, so you’ll need to pull those numbers from your W-2s. Don’t forget state taxes, but those might be on Schedule A.

3. What did you save (and not pull back out of savings)? For a lot of us, this is two helpings of the IRA annual limit, plus some amount into the TSP/401(k) and maybe some college savings too. If you max out retirement savings and automate college savings, your only homework here might be a review of your year-end taxable brokerage account contributions.

Divide that number by 12, and that’s your average monthly spending.

Is It Really That Simple?

Yes and no. It might be helpful to parse out non-discretionary spending, such as mortgage/rent, insurance, education costs, and any charitable giving—expenses you’re probably going to fund in almost all circumstances. But everything else: food, transportation, clothing, utilities, shopping, subscriptions, personal care, pets, hobbies, travel, etc, it fits inside:

Gross Income minus taxes minus savings (minus must-spend spending), divided by 12.

If it doesn’t, we’re pulling money from savings to get through the year, carrying credit card balances, or taking out new loans. Those factors usually don’t escape our attention, so add them to the math if needed.

Does it Matter What We Spend?

No one is still reading unless they answer yes. So here’s why we probably want a decent sense of this number:

1. Are we saving enough? We save so we can spend later. We need to know spending now because it’s probably what we need to spend later. We need some compounding returns to help bridge this gap.

2. Are we saving too much? If we don’t spend much and we save a lot, we’ll probably have trapped gas because of compounding—we’ll have lots of money when we don’t have lots of health and energy in our 70’s+.

3. How much do we need to retire? This is really the same question, but if our current spending is $10K per month, we probably don’t want to tighten our belt in retirement—at least not in the early go-go years.

4. Can we afford to buy an “X?” If we want an RV/boat/vacation home, we need to know where the money comes from for it. Where is the “squish” in the spending that we can reallocate?

5. Is this okay? Sometimes we just want a sense of well-being from knowing that our money is going to the missions we support.

Cleared to Rejoin:

Detailed dollar tracking isn’t for most of us, but we should know what we spend in a year to make sure our money takes care of our needs, wants, and some wishes, too. The math is bar napkin easy. Give it a shot. What do you think about your number?

05/25/2026

Monday Money: Free Financial Planning After SGLI/VGLI

When a service member or veteran passes away, the system usually moves quickly. Claims get filed. Benefits get processed. Paperwork flows.

But there's one benefit that consistently slips through the cracks — not because it doesn't exist, but because almost nobody mentions it.

What You're Entitled to After an SGLI or VGLI Claim

Once a beneficiary receives an SGLI or VGLI payout, a quiet clock starts ticking. For two years from that date, they're eligible for something most people never use:

Up to 40 hours of free financial planning with a fee-only, fiduciary Certified Financial Planner (CFP®).

No products. No commissions. No sales pitch dressed up as advice. Just a credentialed professional who is legally required to act in the client's best interest.

It's called the VA Beneficiary Financial Counseling Service, and you can find it here. The catch is that you must know to look for it in the first place.

Why Most Families Miss It

The VA doesn't proactively connect beneficiaries with a financial planner. There's no warm handoff. No automatic follow-up call. No "here's your next step."

Instead, there's usually a brief mention buried in the Explanation of Benefits package — the same paperwork people are sorting through in the middle of grief, logistics, and a hundred other decisions.

What often happens instead: weeks pass, financial decisions start piling up, and MAYBE someone eventually mentions the program — a casualty assistance officer, a fellow beneficiary, or a follow-up letter from the VA. Only then does the survivor realize the opportunity was there the whole time.

By some estimates, only 30–40% of eligible beneficiaries ever hear about it. That number should be much higher.

Even the Professionals Don't Always Know

Here's what I find particularly striking: many of the people closest to this process have never heard of it either.

Installation financial counselors. Casualty affairs teams. Even financial advisors who specifically serve military families (especially those tied to large national firms selling annuities and whole life policies).

If the professionals in the ecosystem don't know it exists, families are working with a pretty significant information disadvantage.

How the Program Actually Works

The VA sponsors the benefit but contracts administration to a company called ComPsych, which runs the program under the name "Financial Point." They match survivors with fiduciary planners in their area — sometimes within one to two weeks, though timing varies because of the time delays between the loss, the VA claim, the VA’s notification to the survivor and the VA’s notification to its contractor.

That structure is relentlessly confusing. You receive a benefit from the VA, then get handed off to a company you've never heard of, under a program name that's different still. It's easy to see why people hesitate or disengage.
But if you push through the friction, what's on the other side is genuinely valuable.

Over up to 40 hours, a planner can help with cash flow and budgeting, investment decisions, tax considerations, debt management, and longer-term planning. All of it without any product being sold. The conflicts of interest are about as low as possible on the advisor’s side.

Why This Matters

When a large lump sum arrives at the same time someone is processing loss, the wrong kind of attention tends to follow: Sales-driven firms, Insurance products, Advisors whose interests may not line up with the client's, Scammers, Fin-fluencers—basically the part of the industry that belongs in the dust bin of history.

A fiduciary advisor gives the survivor a trusted voice in their corner before the decisions get made. In many cases, the most valuable thing isn't a complex financial strategy. It's having someone objective help you avoid a costly mistake.

If You're Connected to the Military Community

Whether you're a service member, a spouse, a veteran, or someone who advises military families — this program is worth knowing about and worth sharing.

The benefit exists. The funding is there. The advisors are fiduciary.

The only thing missing is awareness.

And that part, we can fix.

05/17/2026

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