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%, ...

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 i...

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...

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 retireme...

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...

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. ...

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 ...

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 y...

It’s not just what you invest in, it’s where you invest it that makes the difference. In this episode of That Financial Guy Show, I break down how to use different types of accounts: 401(k)s, IRAs, Roth IRAs, and brokerage accounts, to maximize growth and minimize taxes. You’ll learn: How each account is taxed and why that matters.Why mutual funds in a brokerage account can create surprise tax bills.How one big index fund in a brokerage account could limit tax-loss harvesting.Why Roth account...

Most retirement planning advice is about saving enough. But what happens when you’ve saved, you’re ready to retire… and you still can’t bring yourself to spend? In this episode of That Financial Guy Show, I dive into the surprising psychology of spending in retirement. You’ll hear: Why many retirees feel guilty about spending—even when the numbers say they’re fine.The three biggest behavioral traps: fear of running out, lifestyle guilt, and market anxiety.How a financial plan acts like a perm...

Everywhere you turn these days, people are talking about Roth conversions like they’re the ultimate retirement hack. But from what I’ve seen in working with real families, the truth is… Roth conversions can be overrated. In this episode of That Financial Guy Show, I share real stories from my own clients — times when a Roth conversion made sense, and times when it would have been a costly mistake. You’ll hear about: A client who almost converted in his peak earning years (and why that would’v...

Most people think saving for retirement is simple: load up the 401(k), defer taxes, and let it grow. But here’s the truth when Required Minimum Distributions (RMDs) hit, Uncle Sam may take a bigger bite than you expect. In this episode of That Financial Guy Show, I break down: Why putting everything into a 401(k) can backfire in retirement.The Go-Go, Slow-Go, and No-Go years of retirement spending—and why your healthiest years matter most.Real client stories where updating the financial plan ...

Two people, same age and income, but very different retirement outcomes—what made the difference? It wasn’t luck—it was strategy. In this video, I break down the five essential moves to make in the final five years before retirement. From maximizing savings and designing a steady income plan, to shielding yourself from market dips, optimizing taxes, and envisioning your ideal lifestyle—this is your blueprint to retire confidently and on your own terms. Don’t let indecision or poor planning de...

Are you wondering if you’re truly ready to retire? In this episode, we explore the 8 key signs you’re ready to retire, covering everything from financial planning and health insurance to emotional readiness and lifestyle goals. Whether you're in your 50s or early 60s and asking, “Can I retire soon?”—this episode breaks down: How to tell if burnout and stress are signs it’s time to retireWhy emotional and mental readiness are just as important as moneyThe importance of retiring to something me...

In this episode of That Financial Guy Show, I breakdown the massive new legislation known as The One Big Beautiful Bill—without the politics, just the financial facts. What’s permanent? What’s temporary? And most importantly… how does this affect your bottom line? We cover: Permanent tax cuts (and what that really means)Bigger standard deductions—especially for seniorsThe new "Senior Bonus Deduction"SALT cap changes and estate tax updatesTax-free tips and overtime (yes, seriously)What’s happe...

🕖 It’s Sunday night. Time for... The Bottom Line. Tonight’s story starts in a garage. Two friends. One big idea. And the company that would put a computer in every home. But just as fast as it all rose… He was out. Fired from the very company he built. Most people would’ve disappeared. He got better. Started over. Bought a little animation studio you might have heard of — Pixar. And then… found his way back What came next? Well… you’re probably holdi...

Retirement isn’t just a financial decision — it’s a relationship one. In this episode of That Financial Guy, I walk you through the three (okay, four) critical conversations every couple should have before they leave the workforce. We’ll cover: How to align on your retirement lifestyle and monthly spendingWhat to do when one spouse wants to retire early and the other doesn’tHow to plan for “what ifs” like illness or losing a spouseAnd why dreaming together might be the most powerful financial...

What happens when you retire… and then unretire just four days later? In this episode of That Financial Guy, I tell the true story of Jim — a 64-year-old IT professional who thought he was ready for retirement until a surprise tax bill and market dip sent him back to work by Tuesday. We’ll walk through his short-lived retirement and unpack the three key lessons that could save you from the same fate: Why retirement isn’t just a math problemHow tax diversification can make or break your income...

In this episode of That Financial Guy, I’m doing something a little different. I’m pulling money lessons from some of the most iconic characters in pop culture — Seinfeld, The Office, and Star Wars. Yep, I went there. What can George Costanza teach us about emotional investing? Why does Michael Scott’s idea of bankruptcy make the perfect case for financial literacy? And what does Anakin Skywalker’s impatience have to do with long-term wealth building? I’ll walk you through: Why following your...

Are your financial decisions really based on logic — or are they being shaped by deep-rooted beliefs you don’t even realize you have? In this episode of That Financial Guy Show, financial planner Keith Wilson explores the concept of money scripts — the unconscious money beliefs formed in childhood that influence how we save, spend, invest, and plan for retirement. You’ll learn about the four most common money scripts: Money Avoidance, Money Worship, Money Status, and Money Vigilance — and how...