That Financial Guy

Most people think they have a financial plan. But in reality, they just have a collection of accounts. In this episode, I break down what a real financial plan actually looks like — not theory, not fluff, but how it works in real life. At its core, a financial plan should address three major areas: retirement, survivorship, and education planning — with tax strategies woven through all of it.  We...

Most financial decisions are not about right or wrong. They’re about tradeoffs. In this episode, I walk through some of the biggest financial tradeoffs I see when working with clients — and how to think through them in a practical, real-world way. We talk about saving more now versus living more now, paying off your mortgage versus investing, retiring early versus retiring comfortably, and how to...

Most people think their portfolio is the problem. Performance is off. The market feels uncertain. Something just doesn’t feel right. So the natural reaction is to start changing investments. But in many cases, the issue isn’t the investments. It’s the lack of a clear plan. In this episode, I walk through why so many people focus on the wrong thing and how a well-structured financial plan creates c...

Some of the most criticized retirement strategies are not bad strategies… they’re just misunderstood. In this episode, I walk through several of the most commonly disliked financial strategies and explain when they may actually make sense within a well-structured plan. I cover topics like annuities, Roth conversions, holding cash, paying off your mortgage before retirement, the 4 percent rule, spe...

In this episode, I answer three real questions that recently came up in client meetings — questions that many people are probably wondering about themselves. First, we talk about 401k savings rates. Should you count your employer match as part of your savings rate? I explain why I prefer to separate your personal savings discipline from the company match, and how to think about what your true savi...

How do ordinary families quietly become millionaires? Not by chasing hot stock tips. Not by building tech startups. Not by getting lucky. In this episode, I break down what I call the Middle Class Millionaire Formula — the simple, disciplined habits that consistently build seven-figure net worths over time. We talk about steady income, avoiding lifestyle creep, participating in employer retirement...

Retirement is not a finish line. It is a phase. In this episode, I wrap up the Plan First Financial Path with Pillar Seven: Live, Adjust, Repeat. After clarifying goals, building a foundation, protecting the plan, investing with purpose, paying less taxes over time, and turning savings into income, this final pillar is about what happens next. Most financial plans assume life stays the same. Same...

This is the moment everything has been building toward. In this episode, I break down Pillar Six of the Plan First Financial Path, Turn savings into income. After clarifying goals, building a foundation, protecting the plan, investing with purpose, and planning to pay less taxes over time, this is where we convert decades of saving into a structured retirement paycheck. I talk about the mindset sh...

Most people think tax planning is about getting the biggest deduction this year. Real tax planning is about paying the least amount of tax over your lifetime. In this episode, I break down Pillar Five of the Plan First Financial Path, Pay less taxes over time. This pillar focuses on making intentional tax decisions that align with your long-term goals, not just the current tax return. We dive deep...

Investing should support your plan, not drive it. In this episode, I break down Pillar Four of the Plan First Financial Path, Invest with purpose. This pillar focuses on slowing down and being intentional about how and where you invest, instead of chasing speculative ideas or the next hot stock tip. We talk about why time horizon matters, how different types of accounts serve different roles, and...

A strong financial plan is not just about growth. It is about resilience. In this episode, I break down Pillar Three of the Plan First Financial Path, Protect the plan. This pillar focuses on building safeguards that keep progress intact when life throws the unexpected your way. We talk about the role of emergency funds, why credit cards are not a substitute for true cash reserves, and how insuran...

Last week, we talked about the first pillar of the Plan First Financial Path, Clarify your goals and priorities. Because once you know where you want to go, the next question becomes practical. Do your day to day money habits actually support those goals? In this episode, I break down Pillar Two of the Plan First Financial Path, Build a foundation. This pillar is all about understanding where your...

Most people think financial planning starts with numbers. In reality, it starts with clarity. In this episode, I break down the first pillar of the Plan First Financial Path, Clarify your goals and priorities. Before any investment, tax, or retirement strategy makes sense, you have to know what your money is actually for. I explain why vague goals lead to reactive financial decisions, how prioriti...

Most people think financial planning starts with picking investments. In reality, it starts with a plan. In this episode, I introduce the Plan First Financial Path, a holistic framework built to help people make smarter financial decisions with intention, not reaction. The Path is made up of seven interconnected pillars that work together to support your specific goals, not a one size fits all che...

In this year in review episode of That Financial Guy Show, Keith Wilson looks back at what actually happened in the markets in 2025 and why it mattered for investors. From the early year market correction known as the Tariff Tantrum to a strong recovery that pushed markets to new highs, Keith breaks down the lessons learned. He also covers the One Big Beautiful Bill, changes to tax planning, the g...

Most people don’t fail financially because they lack information. They fail because behavior breaks down when life gets emotional, unpredictable, or uncertain. In this episode, I explain why a written financial plan changes behavior in a way advice alone never can. A real plan isn’t about predicting the future perfectly. It’s about being prepared when life changes, because life always does. I walk...

 In this episode I walk through one of the most confusing areas in retirement planning today, the rules for inherited IRA and inherited Roth IRA accounts. I start with the simplest scenario, when a spouse inherits an IRA, and then work step by step into increasingly complex situations including non spouse beneficiaries, the ten year rule, Required Beginning Date considerations, eligible designated...

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 oth...

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 sh...

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:  ...

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 no...

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...

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 ho...

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...

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 y...