That Financial Guy

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 + cos...

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...

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 b...

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 t...

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...

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 spendi...

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 you...

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 retire Wh...

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 seniors The new "Senior Bonu...

🕖 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… fou...

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 spending What to do when one spouse wants to retire early and the other doesn’t How to plan for “wha...

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 f...

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...

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...

In today’s episode of That Financial Guy Show , I’m diving into one of the hardest conversations in retirement planning: What do you do when your adult children ask for financial help — but your retirement savings are on the line? As a parent, wanting to help is natural. But giving away too much money during retirement can derail your financial security, strain relationships, and even lead to fina...

What to Do When the Stock Market is Down If you've checked your investment accounts lately and felt a little uneasy — you're not alone. But the good news? Market downturns don’t have to derail your financial future. In this episode, I’m breaking down what really happens when the market drops, what a correction and bear market actually mean, and most importantly — what you can do about it...

 In this episode of That Financial Guy Show , I’m challenging some of the most popular financial "rules" you've probably heard—like the 4% rule for retirement withdrawals, saving 10 times your salary, the 100-minus-your-age rule for investing, or always maxing out your 401(k). The truth is, not all of these rules make sense for everyone. Some are outdated, some are just guidelines,...

In this episode of That Financial Guy, I break down the various investment accounts available for kids and how they can set the foundation for a strong financial future. From saving for college to teaching them about investing early, I will explore the key differences between: 529 Plans – The go-to option for education savings with tax advantages, but with restrictions on how the funds can be used...

In this episode, I take a straightforward look at managing your 401k after retirement. I will be discussing practical options, such as whether to transfer your 401k to an IRA or maintain it in your current plan, and explain the pros and cons of each choice. Our conversation covers: Conversion Options: Evaluating the benefits and drawbacks of different rollover strategies. Withdrawal Strategies:  T...

In this episode, we’re diving into the world of Health Savings Accounts (HSA) —one of the most powerful yet often misunderstood financial tools. We’ll break down how to maximize your HSA benefits , common mistakes to avoid, and strategies to turn your account into a long-term wealth-building asset. Join us as we discuss: ✔️ Who qualifies for an HSA and why it matters ✔️ The best ways to save, inve...

So, you have saved and invested diligently all your working life and the time has come to retire. You feel comfortable,,,, but there could be things you haven't thought about that could ruin the plans you laid forth! LIKE: -Sequence of returns risk - Risk of long term care expenses - Investing too aggressively/speculatively in retirement - Investing too conservatively in retirement - Over con...

There are some new tax law changes for 2025! 401k contribution limits have changed to $23,500. Over 50 is $31,000. There is now a new "super" catch up provision for ages 60 to 63 with a maximum 401k contribution of $34,750. Inherited IRA's will now have to start taking required minimum distributions as well as empty that IRA within 10 years (if you inherited the IRA in 2020 or later...

In this episode I talk with Kelly Augspurger, CLTC, CSA  who is a Long Term Care specialist. We dive into topics of just what is long term care? What are the chances of needing long term care? We break down the myths associated with long term care and how to pay for it? Check out Kelly's YouTube channel @steadfastinsuranceagency Check out Kelly's Podcast @steadfast care planning send you...

If you inherited an IRA or Roth IRA in 2020 or after, The IRS has just changed the rules! The updated 10-year rule and its impact on beneficiaries. Whether you're inheriting a traditional or Roth IRA, understanding these regulations is key to avoiding penalties and maximizing your inheritance. What the 10-year rule means for required distributions? Differences for eligible designated benefici...

Is an Annuity Right for You? 🤔 Considering an annuity but unsure if it’s the right fit for your financial goals? In this podcast, we break down the basics of annuities, their benefits, and potential drawbacks. Whether you're planning for retirement, looking for guaranteed income, or just exploring your options, we’ll help you decide if an annuity aligns with your needs. 📌 What You'll L...