The Money Knight

Tax software makes it easier than ever to file your return on your own, but just because you can do your taxes yourself, doesn’t mean you should. In this episode, Wade explores when DIY tax filing makes sense and when it could lead to costly mistakes. If you’re a W-2 employee with no extra income streams, doing your own taxes might be just fine. But add a rental property, a home sale, a K-1, or retirement distributions, and the ris...

A little hope can go a long way, unless it's the foundation of your retirement plan. In this episode, Wade breaks down five common examples of wishful thinking that can quietly sabotage even the most well-intentioned retirees. From underestimating healthcare expenses to assuming you’ll just “keep working,” Wade explains why these hopeful assumptions can lead to stress, shortfalls, and lost opportunities.

Instead of vague optimism, ...

Millions of people leave jobs each year, and often leave behind their 401(k) accounts too. But what actually happens to that money, and when should you consider rolling it into an IRA? It’s not as straightforward as some advisors make it sound. In this episode, Wade walks through the critical factors to consider before deciding whether to move your old 401(k), including why a rollover isn’t always the right move and what hidden ris...

The headlines are loud and the markets are a bit messy. Your gut might be telling you to something – anything – but you’re not actually sure what to do. In this episode, Wade offers calm, practical guidance to help you avoid panic and make smarter choices during market downturns. If your instinct is to react fast, Wade shows you why slowing down might actually be the best move.

You’ll learn four essential questions to ask when the ...

You’ve done a good job saving, but now what? In this episode, Wade tackles a question many people face as retirement approaches: how do you take solid savings and build a reliable, long-term plan around it? Wade breaks down the essential steps for transitioning from a lifetime of saving to a strategy for generating income, maintaining flexibility, and preparing for uncertainty.

He covers everything from taking inventory of your f...

What does a world-class golf tournament have to do with your financial future? Turns out quite a bit. The Masters is a beautiful reminder of just how much strategy, patience, and long-term focus goes into a great round of golf. Think about it: a hole-in-one may be thrilling, but it won’t win the tournament. Just like chasing a hot stock or one-time windfall will not secure your financial future.  

Today, we’re teeing up a few key l...

April Fool’s Day is all about jokes and pranks, but when it comes to retirement planning, getting fooled can cost you real money. Today, we’re uncovering the beliefs that fool retirees and pre-retirees into making bad financial moves. We’ll cover some of the most common myths that can derail your retirement plans and explain why they might not be as true as they seem.

Should you really claim Social Security as soon as possible? Wil...

The day President Trump took office, he announced plans to implement a 25 percent tariff on goods from Mexico and Canada. Additional tariff conversations have exploded since that day. How might this impact your personal finances and the economy? Today, we’ll explain a bit of the backstory of tariffs and discuss these new tariffs.

For those looking to understand more about managing their finances in the face of uncertainty, this sho...

Financial mistakes can happen at any age, but they can have a particularly significant impact in your 60s. In this episode, Wade discusses six critical financial mistakes that individuals often make during this pivotal decade. Understanding and avoiding these pitfalls can make the difference between a secure retirement and a financially precarious future.

There are numerous financial missteps that can occur as you prepare for retir...

In today's economic climate, the rising cost of healthcare is a pressing concern for many, especially those approaching retirement. In this episode, we will discuss the factors driving these costs and provide insights on how to manage them effectively.

Healthcare expenses have been outpacing general inflation, with costs rising by 5 to 6% annually. According to Fidelity, the average retiree spends about $4,300 per year on out-of-po...

For ​a ​lot ​of ​people, ​giving ​money ​to ​charities ​or beneficiaries ​that ​are ​close ​to ​them ​is ​very ​important. ​But ​oftentimes ​it's ​done ​as ​part ​of ​the ​estate ​planning process. ​Now we’re seeing a trend where more and more people are deciding to give while they’re still alive. Is this a good idea? ​Today's ​episode ​is ​all ​‘giving while you’re living’ and the planning decisions that go into gifting money now.

“Test everything; hold fast what is good.” - 1 Thessalonians 5:21.

In that verse, the Apostle Paul teaches that we should practice discernment in all things and we submit that includes financial advice. So this episode will tackle a common question: What should you ask a potential financial advisor?

When it comes to choosing someone you can trust and who is a good fit for your financial situation, it’s essential to ask the right qu...

Retirement is a phase of life that many of us look forward to, but what happens when it comes earlier than expected? An early retirement can put stress on your finances if you aren’t prepared and this episode will get into the challenges and planning opportunities you can expect.  

Did you know that most Americans retire earlier than planned, often due to unforeseen circumstances like health issues or job changes? According to rese...

In the wake of the recent election, many investors find themselves questioning how political outcomes might affect their portfolios. In this episode, Wade sheds light on why mixing politics with investing isn't always the best strategy and offer listeners valuable insights into the market's reaction to political events.

With this big event finally behind us, let’s talk about where you should be focused moving forward and the key fa...

What makes you unique? That’s a question that you should be asking a prospective advisor during your search for the right fit. In this episode, Wade will break down exactly what sets Chessman Wealth Strategies apart from other financial services companies and explain the core values that we apply to everything we do.

If you’ve listened to any of our shows before, you know the role faith plays in our planning. We’ll tell you more ab...

Financial fraud and scams are seemingly everywhere these days. It seems like barely a day goes by without a new attempt to trick you through email, text, or social media. And now, there’s a new scam out there known as pig butchering.

In this episode, Wade will break down this pig butchering scam, along with other common financial scams that you may be targeted by. We’ll also discuss strategies that you can use to protect yourself f...

Real estate is often heralded as an easy method for generating income in retirement. While it can certainly be a great way to supplement your income, there’s a lot that you want to take into consideration when it comes time to decide whether you want to add a rental property to your portfolio.  

As Wade discusses in this episode, there needs to be a focus on cash flow when you make decisions, as well as a determination on if you wa...

Every couple takes a different approach to their finances, and sometimes that leads to a lack of communication when it comes to money. Are you and your spouse on the same page when it comes to what retirement is going to look like? If not, it’s time to talk.

Listen to this episode where we'll explore why it’s so important for couples to have detailed conversations about their finances and retirement futures. We’ll cover exactly w...

When we work with people to come up with an effective investment strategy, one of the key tools that can help understand and manage the ups and downs of the market is the concept of standard deviation. In this episode, Wade breaks down this crucial metric and explains its significance in investing.

Standard deviation is a statistical measure that quantifies the amount of variation or dispersion of a set of values. In the context of...