In this episode of That Financial Guy Show, Keith Wilson welcomes a special guest — his son, Jack Wilson — for a candid and entertaining conversation about how different generations think about money. From patience vs, impatience to lifestyle creep, adaptability, communication, and the classic “start early” lesson, Keith and Jack break down what younger and older investors can learn from each other.

Jack shares the real financial mindset of today’s 20 somethings, including the pressures of higher costs, student loans, and the desire for flexibility over traditional retirement timelines. Keith offers the perspective of investors who grew up prioritizing stability, consistency, and long term planning. Together, they reveal how these different money lenses can complement each other rather than clash.

The two tackle the myths each generation carries, the habits that hold people back, and the opportunities that open up when families talk honestly about money. You’ll hear about adapting to new financial tools, avoiding lifestyle creep, building patience, and using early habits to your advantage no matter your age.

If you want a fun, relatable look at money through two different generational perspectives — with plenty of father son banter mixed in — this episode delivers real insights anyone can use.

Helping you to be wise with your money!
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The first decade of retirement isn’t just another phase — it’s the most important chapter of your entire retirement journey.

In this episode of That Financial Guy Show, Keith Wilson breaks down why the first 10 years set the trajectory for everything that comes after. From spending patterns and taxes to Social Security timing, sequence of returns risk, identity shifts, and health — this episode shows why your early retirement decisions matter more than you think.

You’ll learn:
 • Why the “Go-Go Years” (your 60s and early 70s) set the pace for spending
 • How sequence of returns can make or break a portfolio in the early years
 • Why your first decade is a tax-planning goldmine
 • How Social Security timing shapes long-term income
 • The emotional side of retirement that people don’t talk about
 • Common mistakes retirees make early — and how to avoid them
 • How to build habits that make the next 20 years smoother and more secure

Retirement isn’t something that happens to you — it’s something you design.
And the first decade is where the blueprint comes together.

🎧 Tune in to learn how to make the early years of retirement intentional, flexible, and financially confident.

Helping you to be wise with your money!
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Retirement isn’t just about what you earn — it’s about what you keep.

In this episode of That Financial Guy Show, Keith Wilson breaks down the overlooked tax traps that quietly drain retiree income and create unnecessary stress. From Social Security taxation to IRMAA surcharges, Keith explains how to spot — and avoid — the hidden tax bites that come from well-intentioned decisions.

You’ll learn:
 • How the “stacking rule” for income determines whether your capital gains are taxed at 0%, 15%, or 20%
 • Why even municipal bond interest can make your Social Security taxable
 • How one large IRA withdrawal can raise your Medicare premiums two years later
 • The truth about Required Minimum Distributions (RMDs) and how Roth conversions or Qualified Charitable Distributions (QCDs) can help
 • Why mutual fund distributions can create surprise tax bills in taxable accounts
 • What the 3.8% Net Investment Income Tax (NIIT) really applies to
 • How to design an income sequence across taxable, tax-deferred, and Roth accounts to stay efficient for life

Because managing taxes in retirement isn’t about doing more — it’s about doing things in the right order.

🎧 Tune in for a clear, practical deep dive into how to make your money last longer by keeping more of what you’ve already earned.

Helping you to be wise with your money!
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Every year teaches investors something new — and 2025 was no exception.

In this episode of That Financial Guy Show, Keith Wilson looks back at the biggest financial lessons from the year — what the markets reminded us, what changed for good, and what timeless truths still hold.

You’ll learn:
 • Why the February–April correction proved that patience beats panic every time
 • How corrections are normal (they happen nearly every year) — and why staying invested works
 • Why cash is useful, but not a long-term strategy
 • How The One Big Beautiful Bill changed the tax landscape — and why smart planning still matters
• Why inflation never really disappears (and what it means for retirees)
• How simplicity and clarity can bring more confidence than complexity ever could
• And why the best financial plan is one you keep updating, not one you file away

Because real financial success isn’t about predicting the next move — it’s about learning, adapting, and preparing for whatever comes next.

🎧 Tune in to reflect on 2025 — and make sure 2026 starts on the right foot.

Helping you to be wise with your money!
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You’ve spent decades focused on growing your money — but once you retire, the game completely changes.

In this episode of That Financial Guy Show, I explain why successful retirement isn’t about chasing returns, it’s about building reliable income that lasts.

You’ll learn:
 • The crucial difference between investment planning and income planning
 • How to protect yourself from sequence-of-returns risk — the silent portfolio killer
 • Why creating a “retirement paycheck” is more important than tracking daily market swings
 • How to organize your money into short-term, mid-term, and long-term buckets for stability and growth
 • The role of taxes and withdrawal order in maximizing retirement income
 • How to build flexibility so your plan holds up in both good and bad markets

Because the real goal isn’t to have the biggest portfolio — it’s to have the most dependable lifestyle.

🎧 Tune in and learn how to turn your savings into an income plan that works as hard as you did.

Helping you to be wise with your money!
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They say opposites attract… until it’s time to talk about money.

In this episode of That Financial Guy Show, I unpacke the emotional and practical side of managing money as a couple — and why love and finance often speak completely different languages.

You’ll learn:
 • Why most money fights aren’t really about money at all — and what they actually mean
• The four common money personalities and how they clash (Saver, Spender, Avoider, Planner)
• How couples miscommunicate about retirement goals, daily spending, and “financial fairness”
• Simple steps to create transparency, reduce resentment, and build teamwork around finances
• How to turn money from a source of stress into a shared vision for your future together

Whether you’re newly married, approaching retirement, or somewhere in between — this episode helps you bridge the financial gap between love, logic, and lasting partnership.

Because financial planning isn’t just about numbers — it’s about understanding the person across the table.

Helping you to be wise with your money!
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Your Social Security filing decision isn’t just about you, it’s about your spouse, your survivor, and your family’s long-term income.

In this episode of That Financial Guy Show, I break down one of the most misunderstood parts of retirement planning: spousal and survivor benefits. You’ll learn:

• How spousal benefits actually work and why they’re capped at 50% of your spouse’s Full Retirement Age amount
 • How delaying your own benefit can permanently raise your spouse’s survivor benefit for life
• What divorced spouses need to know, including the 10-year rule and the remarriage age cutoff
• How recent changes in 2025 repealed the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO), increasing benefits for millions of retirees
• Smart timing strategies to coordinate Social Security with pensions, annuities, and portfolio income
• How to protect your plan from the sequence-of-returns risk in early retirement

If you’re married, divorced, or just starting to plan your retirement income, this episode will help you make smarter, more confident Social Security decisions — and maybe even boost your lifetime benefits

Helping you to be wise with your money!
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You’ve probably heard it before: “Just max out your 401(k) and you’ll be fine.”
But here’s the truth, if that’s your only strategy, you could be setting yourself up for a massive tax problem later.

In this episode of That Financial Guy Show, Keith Wilson explains why focusing only on your 401(k) can limit your flexibility in retirement and what to do instead. You’ll learn:
• Why every dollar in your 401(k) is fully taxable later and how that can lead to higher taxes and Medicare premiums.
• Why your savings rate matters more than contribution limits.
• How to use a 25% savings rate as a framework for smarter, more balanced saving.
• The power of tax allocation by spreading savings across 401(k), Roth, and brokerage accounts.
• How building tax flexibility now gives you more control over your retirement income later.

Because real wealth isn’t about maxing out a single account, it’s about creating options across all of them.

🎧 Tune in and learn how to make your savings work smarter, not just harder.

Helping you to be wise with your money!
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We’ve all heard the retirement “rules of thumb”, save a million bucks, withdraw 4%, you’ll be fine. But what if those old rules are setting you up for mistakes?

In this episode of That Financial Guy Show, Keith Wilson takes aim at the five most common retirement myths that can derail even the smartest savers. You’ll learn:

• Why the “$1 Million to Retire” rule is misleading (and how inflation + cost of living change everything).
• The truth about Social Security, why it’s not going away, and what really matters.
• Why the famous 4% rule isn’t one-size-fits-all (and what Bill Bengen, Michael Kitces, and even Dave Ramsey get wrong).
• How lifestyle creep quietly eats away at high earners and how to stop it without living like a monk.
• Why money alone doesn’t guarantee happiness in retirement and what to focus on instead.

Retirement isn’t about myths, magic numbers, or fear it’s about clarity, flexibility, and purpose.

🎧 Tune in now to learn what really works when it comes to building and living your best retirement.

Helping you to be wise with your money!
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If you’re in your 40s or 50s and feel like you’ve fallen behind on retirement savings, this episode is for you. Maybe you’ve heard the advice to start investing early—but life happened, and now you’re wondering if it’s too late to build a secure future. Spoiler: it’s not. In this episode of That Financial Guy, I’ll walk you through ten realistic, actionable steps to help you catch up, rebuild, and create a retirement plan that works—starting right now. From money mindset shifts and tracking your spending, to building an emergency fund, increasing your income, and redefining what retirement can look like, we’re covering it all. No fluff. Just clear, practical guidance for people ready to take control. You’re not too late—you’re right on time.

Helping you to be wise with your money!
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