Cover Your Assets KC Podcast

Many grandparents want to leave a meaningful financial legacy, but choosing the right assets to pass along isn't always as straightforward as it seems. In this episode, David explores a common estate planning question and discusses why one approach may involve additional tax and administrative considerations. He also reviews several alternative strategies families may want to consider when thinking about transferring wealth to the ...

Roth IRAs can be a powerful retirement planning tool, but they come with some surprisingly confusing rules. In this episode, David breaks down the two different Roth IRA five-year rules and explains why they have almost nothing to do with each other. Learn how withdrawals are taxed, when the 10% early withdrawal penalty may apply, and why Roth conversions could create unexpected complications for some younger investors. David also ...

Most people know Roth IRAs don’t normally have required minimum distributions, but things can change when someone inherits one. In this episode, David explains how inherited Roth IRA rules work, why beneficiary type matters, and when the IRS may still require distributions even from tax-free accounts. David also walks through real-world examples and highlights why beneficiary planning has become much more complicated after re...

David tackles two listener questions from folks standing right on the doorstep of retirement. He explores how timing a large vacation and a sick-leave payout could affect taxes and savings options, and then looks at whether it makes sense to retire before Medicare kicks in, given healthcare costs and subsidies. Throughout, David discusses how the “last mile” decisions could make a difference in retirement confidence.

He...

What happens when a 22-year-old suddenly inherits a significant sum with no guardrails in place? In this episode, David and Walter unpack a listener scenario involving an uncle worried about his nephew’s financial future after an unexpected inheritance. They explore the potential risks of unrestricted wealth, the possible role of trusts, and how family members or advisors can step in to provide guidance.

Here’s some of ...

What happens to your money after you’re gone isn’t always as simple as passing it down. David walks through a reality many families don’t talk about, and why planning ahead can make a meaningful difference. This isn’t just about protecting assets; it’s about protecting people. With the right structure and conversations, you can turn an inheritance into something that lasts.

Here’s some of what w...

For many, the annual financial review is just a routine- show up, review the numbers, and leave. But what if that hour could be very valuable for your financial life? If you’re not leaving with clarity and confidence, you might be missing out. David explains how to turn your review into a meaningful conversation by asking the right questions, focusing on your plan, and actively participating.

Here’s some of what we disc...

Two listener questions spark a conversation about the emotional and practical sides of retirement planning. David talks about strategies for easing back into the market after sitting on the sidelines and how retirees can think about taxes when withdrawing from IRAs, brokerage accounts, and Roth accounts. These are the kinds of questions many investors face as they transition into retirement, and without the right guidance, the wron...

When you hire someone to help with your money, you probably assume they’re legally required to act in your best interest. But here’s the catch: not all financial professionals are held to the same standard. In this episode, David breaks down the often-confusing distinction between brokers and fiduciaries, and why it matters for your retirement confidence.

Here’s some of what we discuss in this episode:

⚖️ The lega...

In this mailbag episode, David answers two practical listener questions about managing unexpected financial opportunities. One listener recently paid off their mortgage and now has an extra $3,000 per month to invest, while another is navigating the tax implications of inheriting an IRA. David walks through several potential options for putting extra cash to work- ranging from CDs and brokerage accounts to fixed annuities- while al...

Financial media loves simple answers: always do this or never do that. But real financial planning doesn’t work that way. Most of the biggest decisions people face in retirement live in the gray. David pulls back the curtain on the sensational advice dominating YouTube and financial media. Instead of chasing rigid rules, he explains why thoughtful coordination across multiple planning areas could potentially produce better ou...

Inheriting a home often comes with a lot of anxiety, especially around taxes. Many heirs assume selling means a massive tax bill, but that concern is often misplaced. In this episode, David breaks down what really happens when you inherit a house, why taxes are usually less painful than expected, and what non-tax issues can complicate the decision. If you’re facing an inherited property, or expect to someday, this conversatio...

The amount of life insurance you need changes significantly as your life and responsibilities evolve. David shares practical considerations for thinking through coverage needs at different stages of life, from early adulthood through retirement years. Rather than focusing on one-size-fits-all answers, David offers general tips to help listeners think more clearly about how life insurance might fit into a broader financial picture.

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Feeling behind on retirement savings can be overwhelming, but it doesn’t mean you’re out of options. In this episode, David walks through five practical steps to help you regain clarity and momentum, whether you’re early in your career or approaching retirement. From tracking spending habits to maximizing workplace retirement plans, this episode focuses on actions you can actually control.

Here’s some of wh...

Today, David is breaking down some of the year’s biggest headlines and what they may mean for your plan moving forward. 2026’s headlines might look different, but the same drama will likely exist. So, what can you do? Aim to control your plan, your savings habits, and your long-term strategy. That’s what can help turn a chaotic year into a confident retirement path.

Here’s some of what we discuss in this ep...

Most people ask good retirement questions, but not always the right ones. In Part 2 of this series, David Dickens shares five more “better questions” pulled straight from real client meetings, revealing how small shifts could lead to better retirement decisions.

From Social Security timing to mortgage payoff strategies and more, we’ll explain how reframing the way you ask the question might change the quality of t...

Sometimes the smartest move in retirement planning isn’t knowing all the answers. It’s about learning to ask better questions.

In this episode of Cover Your Assets KC, David walks through five common financial questions people ask, and then explains how to reframe them to get better results. From “How much money do I need to retire?” to “Where can I pay the lowest fees?”, we’ll explain how ...

Most people think financial planning is about calculators, spreadsheets, and strategies. But that’s only half the story. The fact is, your feelings about money can have just as much impact on your retirement as the numbers do. Today, David explores the emotional side of planning and how your legacy goals can be shaped by what you feel, not just what you know.

Here’s some of what we discuss in this episode:

🧩 Whole-Pers...

Before we get started, please note that when we use the terms ‘safe,’ ‘safety,’ or ‘safe money’ in today’s discussion, we’re referring generally to strategies designed to help manage risk, not to any product or investment that is guaranteed or free from loss or any other risks. All investments involve risk, including possible loss of principal. While some products may offer a level of...