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!
To see more videos discussing personal finance Subscribe:
https://www.youtube.com/channel/UCbDA...

For more resources: 👉 https://wfa-nc.com/insights

📝 Get your Free Retirement Plan checkup
https://wfa-nc.com/retirement-plan-ch...

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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!
To see more videos discussing personal finance Subscribe:
https://www.youtube.com/channel/UCbDA...

For more resources: 👉 https://wfa-nc.com/insights

📝 Get your Free Retirement Plan checkup
https://wfa-nc.com/retirement-plan-ch...

To schedule a complimentary consultation with me: 👉...