The Money Knight

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
Many retirees are caught off guard when they discover Medicare isn’t always truly “free.” If your income is too high, you could face a hidden surcharge called IRMAA (Income Related Monthly Adjustment Amount), that can potentially reduce your Social Security check by thousands each year. In this episode, Wade breaks down what IRMAA is, who it impacts, and how to plan ahead so it doesn’t derail your retirement income.
We’ll explain the income thresholds that trigger IRMAA, why widows often get hit harder, and the types of income that can push you into higher Medicare costs. He also shares strategies to help minimize the impact, from Roth conversions and QCDs to charitable giving techniques and tax diversification.
For this week’s Kingdom Minute, Wade reflects on Jesus’ words in Luke, warning us to “be on guard against all covetousness.” True security comes not from collecting more, but from aligning our money and choices with values that last. Instead of striving for more, we’re called to use what we have with wisdom and purpose, investing in things that truly last.
Here’s some of what we discuss in this episode:
🧾 IRMAA: a hidden Medicare surcharge based on income
💸 Who is most likely to be impacted by IRMAA penalties
🔄 Strategies to avoid paying extra premiums
🌱 Tax diversification may help minimize surprises
 
Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
The opinions voiced in The Money Knight podcast with Wade Chessman of Chessman Wealth Strategies are for general information only and are not intended to provide specific advice or recommendations for any individual. Past performance is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing.
Investment advisory services offered through CWM, LLC, an Investment Advisor. Carson Partners, a division of CWM, LLC, is a nationwide partnership of advisors.

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
Retirement can feel overwhelming when so much seems out of your control. Markets rise and fall, tax laws shift, and Social Security’s future makes the news every few months. But here’s the good news: stressing about those things won’t improve your retirement. What will help is focusing on the four key areas you can control. In this episode, Wade shares the levers that actually move the needle for retirees and pre-retirees.
Wade explains how to avoid emotional decisions that could derail your plan and covers everything from managing your market risk exposure to building reliable income streams. He also dives into proactive tax planning—why it’s written in pencil, not pen—and how to think about Social Security realistically without leaning on it as your primary income source. You can’t stop volatility or predict what Congress will do next, but you can put yourself in a stronger position with the choices you make today.
Here’s some of what we discuss in this episode:
📉 Control how much market risk you take on
🕰️ Plan for longevity, because no one knows how long they’ll live
💵 Use tax planning to your advantage (not just tax prep)
🧭 Social Security’s true purpose: safety net, not primary retirement income
🗝️ The power of planning gives you control where it matters most
 
Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
The opinions voiced in The Money Knight podcast with Wade Chessman of Chessman Wealth Strategies are for general information only and are not intended to provide specific advice or recommendations for any individual. Past performance is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing.
Investment advisory services offered through CWM, LLC, an Investment Advisor. Carson Partners, a division of CWM, LLC, is a nationwide partnership of advisors.

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
 
On a recent hiking trip, Wade noticed how Moses, his Cavapoo, darted after every squirrel, bird, and chipmunk along the trail. It was funny to watch, but it also reminded him of how investors behave when chasing the latest “hot” trend. Many of us have been tempted by tech stocks, crypto, and gold, only to jump in at the wrong time and drain our savings and sanity in the process. In this episode, Wade draws parallels between Moses’ squirrel-chasing and investor habits, contrasting that with the calm, steady retrievers who stick to the path.
He shares why defining your goals, staying leashed to your plan, and ignoring distractions are keys to lasting success. Plus, Wade reflects on timeless biblical wisdom about patience, diligence, and building wealth little by little. If you’ve ever been tempted by the “next big thing,” this conversation is a reminder that financial freedom isn’t about chasing squirrels; it’s about staying on the trail. Tune in to learn how to keep your plan and your future steady.
For this week’s Kingdom Minute, we’re reminded how chasing quick wins- whether it’s money, success, or the next “shiny thing”- often leaves us worn out and empty-handed. God’s Word calls us instead to steady, faithful stewardship, where wealth and wisdom are built little by little. True growth comes through patience, discipline, and walking faithfully with His plan.
 
Here’s some of what we discuss in this episode:
🥾 Picking your trail: define goals before the journey
🐕 DOG acronym: dangers, obstacles, and gaps on the path
💡 Harness lessons: freedom within guidelines builds discipline
🌲 Enjoying the hike: wealth is about the journey, not just the destination
📖 Proverbs & Galatians: “little by little” growth is God’s way
 
Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
The opinions voiced in The Money Knight podcast with Wade Chessman of Chessman Wealth Strategies are for general information only and are not intended to provide specific advice or recommendations for any individual. Past performance is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing.
Investment advisory services offered through CWM, LLC, an Investment Advisor. Carson Partners, a division of CWM, LLC, is a nationwide partnership of advisors.

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
The Big Beautiful Bill may not have overhauled the entire tax system, but it quietly introduced a wave of limited-time tax opportunities, and the clock is already ticking. In this episode, Wade shares seven strategic tax moves to consider before many of these provisions expire in 2028. These changes could impact how much you owe, how much you save, and how fast you reach your goals.
Buried in the bill are real, actionable tax advantages—if you know where to look. Charitable deductions, auto loan interest write-offs, bonus depreciation—there’s a lot packed into the Big Beautiful Bill, and Wade breaks it all down in plain English. Miss this window, and you might be leaving money on the table. The rules have changed, but only for a few years. What you do now could shape your finances for the next decade.
For this week’s Kingdom Minute, Wade shares key biblical perspectives on taxes, pointing to scriptures in Matthew and Romans. He explains that while paying taxes is a civic duty, it's also part of honoring God’s appointed authorities. Wade also reminds us that generosity, like charitable giving, is both encouraged in scripture and recognized by the tax code.
 
 
Here’s some of what we discuss in this episode:
🎁 Front-load charitable giving to maximize new deductions
🍽️ No taxes on tips—if you report properly
🏗️ Use Section 179 and QBI to your advantage
🏘️ Bunch property taxes for max SALT deduction
👶 “Trump Accounts” offer $1K seed + tax-deferred growth
📖 Biblical reflections on taxes in the Kingdom Minute
 
Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
The opinions voiced in The Money Knight podcast with Wade Chessman of Chessman Wealth Strategies are for general information only and are not intended to provide specific advice or recommendations for any individual. Past performance is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing.
Investment advisory services offered through CWM, LLC, an Investment Advisor. Carson Partners, a division of CWM, LLC, is a nationwide partnership of advisors.

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
A new tax bill has officially passed (you’ve probably heard it mentioned as the “Big Beautiful Bill”). And while most headlines are focused on politics, Wade is focused on what really matters: how it impacts your retirement and financial plan. The choices you make in the next year or two could have a significant impact on how much you keep and how much goes to Uncle Sam.
In this episode, Wade breaks down what’s changing (and what’s not), including updates to tax brackets, standard deductions, and SALT caps. The good news? There are some new opportunities for retirees and pre-retirees to take advantage of, but it’s still a relatively short window to act before some of these new components expire in 2028, or before a new Congress changes things again.
Here’s some of what we discuss in this episode:
📊 Trump-era tax brackets extended beyond 2025
💸 New $12K deduction for couples over 65
🏡 SALT cap raised, especially impactful in high-tax states
🪙 Bonus depreciation win for small biz & landlords
🎁 Above-the-line deduction now available for givers
🚘 Auto loan deduction & EV credit deadlines
Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
The opinions voiced in The Money Knight podcast with Wade Chessman of Chessman Wealth Strategies are for general information only and are not intended to provide specific advice or recommendations for any individual. Past performance is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing.
Investment advisory services offered through CWM, LLC, an Investment Advisor. Carson Partners, a division of CWM, LLC, is a nationwide partnership of advisors.

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
 
The thing about assassins in the real world is that they’re sneaky and you don’t see them coming. The same is true for retirement planning. It’s not always the obvious threats that do the most damage. It’s the ones that creep in quietly, unnoticed, and unplanned for. In this episode, Wade breaks down what he calls the “retirement assassins,” those stealthy financial risks that can sneak up and completely derail your retirement if you’re not careful.
Wade walks through the biggest threats he sees time and time again: like inflation, losing a spouse, or just living longer than you planned for. These aren’t flashy risks, but they’re real, and they can quietly eat away at your savings if you’re not paying attention. The good news? With the right plan in place, none of them have to take you out. This episode is all about spotting the silent threats before they strike, so you can defend your retirement before it ever gets ambushed.
For this week’s Kingdom Minute, Wade reminds listeners that while we talk a lot about financial planning, it’s important to remember that trusting God doesn’t mean avoiding preparation. Scripture supports thoughtful, wise planning (Proverbs 21:5, 24:27, and 15:22), and biblical figures like Noah and Joseph are clear examples of faithful planners. Planning allows you to align your resources with God’s purpose, create margin for generosity, and act with intention.
Here’s some of what we discuss in this episode:
📉 Inflation: the slow and steady threat to your income
🏥 Long-term care: the most avoided conversation in retirement
💸 Taxes: today’s rates won’t last forever
🕊️ Widowhood: financial strategies for life’s hardest moment
⏳ Longevity: when a long life becomes a financial risk
Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
The opinions voiced in The Money Knight podcast with Wade Chessman of Chessman Wealth Strategies are for general information only and are not intended to provide specific advice or recommendations for any individual. Past performance is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing.
Investment advisory services offered through CWM, LLC, an Investment Advisor. Carson Partners, a division of CWM, LLC, is a nationwide partnership of advisors.

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
Giving to charity feels great. But what if you could do it in a way that also gave you a tax break, without needing to itemize? That’s where a Qualified Charitable Distribution (QCD) comes in. And if you're over 70½, this could be a game-changer. In this episode, Wade brings in a special guest: Sean Phillips, Vice President of Wealth Management at Chessman Wealth. Together, they break down everything you need to know: what QCDs are, how they work, and why the IRS finally made a move to improve how they’re reported.
It’s a great step, but there’s still a lot of confusion. Wade and Sean make it easy to understand how QCDs can reduce your taxable income, count toward your RMDs, and help you support causes you care about—without triggering more tax headaches. They also share why custodians aren’t exactly racing to implement the new IRS update, what to watch out for when reporting QCDs, and how to make sure your CPA and advisor are on the same page.
Here’s some of what we discuss in this episode:
📜 What a QCD is & why it matters
💸 Why writing a check might cost you more in taxes
📉 Reduce your taxable income with QCDs
🧾 The IRS’s new QCD reporting rule (and why custodians aren’t ready)
⚠️ The mistake that leads people to pay taxes they didn’t need to
 
Connect with Sean: https://www.chessmanwealth.com/team-members/sean-phillips/ 
 
Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
The opinions voiced in The Money Knight podcast with Wade Chessman of Chessman Wealth Strategies are for general information only and are not intended to provide specific advice or recommendations for any individual. Past performance is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing.
Investment advisory services offered through CWM, LLC, an Investment Advisor. Carson Partners, a division of CWM, LLC, is a nationwide partnership of advisors.

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 risks start to grow quickly.
Wade shares the most common errors he sees in self-filed returns, from misreporting investment income to missing out on valuable deductions. He also explains the key difference between tax preparation and true tax planning, and how financial advisors and CPAs can work together to spot opportunities before they expire. If you’ve ever used DIY tax software and found yourself wondering if you did it right, you’re not alone. Find out how you can make more informed choices for next year’s tax season.
Here’s some of what we discuss in this episode:
🧾 When DIY taxes actually make sense
🚨 Common self-filing mistakes that trigger IRS letters
💡 The difference between tax prep and tax planning
🤝 How advisors and CPAs team up for better outcomes
🧠 Missed deductions = missed opportunities
Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
The opinions voiced in The Money Knight podcast with Wade Chessman of Chessman Wealth Strategies are for general information only and are not intended to provide specific advice or recommendations for any individual. Past performance is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing.
Investment advisory services offered through CWM, LLC, an Investment Advisor. Carson Partners, a division of CWM, LLC, is a nationwide partnership of advisors.

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, it’s smart to have a plan grounded in reality. Wade shares real client experiences, practical alternatives, and stress-test strategies that can help you prepare for the what-ifs of retirement with clarity and confidence. This episode will help you trade guesswork for peace of mind, whether you’re 5 years away from retiring or already in the “go-go” years.
For this week’s Kingdom Minute, Wade discusses the spiritual significance of money in the Bible, and what it reveals about our hearts and what we truly value.
 
Here’s some of what we discuss in this episode:
💸 Counting on lower taxes in retirement? Think again.
🏥 A common long-term care myth
🍽️ Why you might spend more, not less, after retiring
💰 Can Social Security really carry you through?
🏃‍♂️ The risky plan of “I’ll just keep working”
 
Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
The opinions voiced in The Money Knight podcast with Wade Chessman of Chessman Wealth Strategies are for general information only and are not intended to provide specific advice or recommendations for any individual. Past performance is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing.
Investment advisory services offered through CWM, LLC, an Investment Advisor. Carson Partners, a division of CWM, LLC, is a nationwide partnership of advisors.

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 risks might be lurking in accounts you’ve forgotten about.
You’ll also hear about the consequences of scattered investments, how “de-worsification” can happen when old accounts accumulate, and the real advantages (and limitations) of IRAs. He also covers common mistakes to avoid, the importance of a thorough cost-benefit analysis, and how tax implications can vary depending on how the rollover is handled.
For this week’s Kingdom Minute, Wade explores how to leave an inheritance with both wisdom and love. Instead of dividing everything equally by default, it encourages parents to consider each child’s unique needs and situation. Clear communication and thoughtful planning can help prevent conflict and strengthen family unity.
Here’s some of what we discuss in this episode:
📂 What really happens when you leave your 401(k) behind
⚖️ The pros and cons of rolling over into an IRA
📉 Why too many accounts can lead to “de-worsification”
🧭 How investment guidance fits into your rollover decision
🗣️ A biblical approach to inheritance that encourages unity
 
Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
The opinions voiced in The Money Knight podcast with Wade Chessman of Chessman Wealth Strategies are for general information only and are not intended to provide specific advice or recommendations for any individual. Past performance is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing.
Investment advisory services offered through CWM, LLC, an Investment Advisor. Carson Partners, a division of CWM, LLC, is a nationwide partnership of advisors.