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That Financial Guy is a podcast dedicated to making financial planning and investing easy to understand and to implement. Keith and Jack Wilson are practicing financial advisors who own a financial planning firm, Wilson Financial Advisors. They are a father and son team "spreading a wealth of information" helping you along your personal finance journey. Whether its personal finance including investments, retirement planning, estate planning, financial planning, college funding, budgeting and more you will find it here! Securities and Advisory Services offered through LPL Financial, a Registered Investment Advisor. Member FINRA/SIPC.
54 Episodes
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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 checklist. Those seven pillars are Clarify your goals and priorities, Build a foundation, Invest wit...
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 government shutdown, interest rate cuts, the surge in artificial intelligence stocks, and why a so...
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 through real client stories, including how one client’s commission-based income led to a larger ...
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 beneficiaries, stretch IRA rules for pre 2020 deaths, and how to determine whether the dece...
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 hi...
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...
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...
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