The Money Knight

Inside the Smart Choices Wealth Management Process

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
In this episode, Wade walks through what a structured, relationship-based planning experience actually looks like from start to finish. You’ll hear why good planning isn’t about quick recommendations, but about clarity, confidence, and follow-through. If you’ve ever wondered what working with us would be like, this conversation sets expectations.
Wade emphasizes that the Smart Choices process is ultimately about stewardship- helping clients make wise, intentional choices with the resources God has provided so they can worry less and enjoy life more.
Here’s some of what we discuss in this episode:
🔍 Discovery Meeting: Understanding goals, concerns, and priorities
🤝 Mutual Commitment: Deciding if the relationship makes sense
🛡️ Advanced Planning: Protecting, growing, and transferring wealth
📈 Progress Monitoring: Ongoing reviews and adjustments
📄 Preparation Tips: What to bring to the first meeting
 
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.

When Should You Do a Roth Conversion?

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
When does a Roth conversion actually improve a retirement plan? Roth conversions can be powerful, but only when they’re done with purpose. Wade highlights when conversions help, when they can backfire, and why guessing is one of the worst things you can do.
For this week’s Kingdom Minute, Wade reflects making financial decisions with wisdom, patience, and a long-term perspective. Rather than chasing short-term tax wins, the focus is on aligning money decisions with purpose, responsibility, and care for the future.
Here’s some of what we discuss in this episode:
🔄 Roth Strategy: How conversions support long-term planning
📊 Tax Bracket Factors: Income changes, timing, and opportunity years
🧠 Strategic Considerations: Coordinating Roth moves with your full plan
🧾 Side Effects Matter: Social Security, Medicare, and tax ripple effects
 
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.

Charitable Giving: Donating Assets vs Cash

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
Some people think generosity starts and ends with writing a check. But what if what you give matters just as much as how much you give? In this episode, Wade explains the difference between donating cash and donating assets, and why asset-based giving can create powerful tax advantages while increasing your impact.
For this week’s Kingdom Minute, Wade reflects on Charles Dickens' "A Christmas Carol," drawing parallels to biblical teachings about wealth and stewardship. He emphasizes that true riches come from honoring God with our resources, rather than accumulating possessions.
Here’s some of what we discuss in this episode:
💸 Cash vs. Assets: Rethinking how you give
📈 Tax Benefits: Turning tax dollars into giving dollars
🧾 Estate Planning: Charitable bequests done right
🤝 Advisor Role: The power of coordinating generosity with strategy
🎄 Kingdom Minute: A holiday reflection on stewardship
 
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.

How to Ask Better Questions About Retirement

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
You’ve heard the saying, “There’s no such thing as a bad question.” But in retirement planning… some questions are definitely better than others. The way you frame your question often determines the quality of your answer and, in some cases, the quality of your retirement. In this episode, Wade shows how small shifts in the way you frame your questions can completely transform your financial clarity, confidence, and long-term outcomes.
He shares practical examples, real client stories, and simple frameworks to help investors think beyond surface-level answers and toward a true, personalized financial plan. The episode finishes with a powerful Kingdom Minute about budgeting as biblical stewardship.
Here’s some of what we discuss in this episode:
💵 “How much do I need?” → “How much income do I need?”
📈 “Highest return?” → “Return that supports my plan.”
🧾 “Lower taxes now?” → “Lower taxes now and later.”
🕒 “62 or 70?” → “Best Social Security strategy for my plan.”
⚖️ “Avoid risk?” → “Take the right amount of 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.

Is Social Security Going Broke? Facts and Strategies

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
 
Wade tackles the endless headlines about Social Security running out of money and explains why the fear around it often overshadows the facts. This conversation brings perspective to an issue people worry about far more than they need to, especially when planning for retirement. If you’ve ever wondered what’s true, what’s political noise, and what actually matters for your retirement plan, this episode will give you the clarity you’ve been looking for.
Here’s some of what we discuss in this episode:
❗ Social Security Myths: separating fear from reality
📜 The Real History: why predictions of collapse have been wrong for decades
💸 Government Spending Factors: what headlines leave out
⚙️ Possible Fixes Ahead: how adjustments, not collapse, are most likely
🧩 Personalized Planning: how to make smart claiming decisions for your situation
The Dallas Morning News Article: 
https://www.dallasnews.com/timeless-in-texas/2025/09/21/ye-of-little-faith-little-green-spacemen-and-social-security/
 
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.

What Can You Expect at Advisor Meetings?

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
Meeting with a financial advisor for the first time can feel intimidating, but it doesn’t have to be. In this episode, Wade walks through exactly what to expect when you schedule time with Chessman Wealth Strategies. From the first phone call to the discovery meeting and beyond, Wade explains how his team helps clients clarify goals, uncover financial “blind spots,” and design a personalized Smart Choices Wealth Management plan.
For this week’s Kingdom Minute, we discuss timeless biblical wisdom for how parents should consider passing wealth to the next generation. Should every child get the same amount, or should they receive an inheritance according to their individual needs and circumstances? Tune in the find out!
Here’s some of what we discuss in this episode:
💬 Discovery Meeting: getting to know you, your goals, and what matters most
📈 Smart Choices Strategy: developing a personalized plan to guide your finances
📅 Easy Scheduling: how to book a meeting and start the process hassle-free
🎯 No Clear Goals? how Wade helps clients clarify what they really want
 
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.

Retirement Health Care Costs Just Jumped Again (2025 Update)

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
Health care costs in retirement are climbing faster than ever, and the newest Fidelity estimate proves it. The average 65-year-old couple retiring today will need $172,500 to cover health care expenses, up dramatically from just a few years ago. In this episode, Wade breaks down what’s driving these rising costs, the biggest misconceptions about Medicare coverage, and how to plan ahead so these expenses don’t derail your retirement.
Here’s some of what we discuss in this episode:
💰 Rising Costs: Fidelity’s 2025 estimate shows retiree healthcare expenses climbing sharply
🧭 Plan Ahead: why healthcare planning is essential to a successful retirement strategy
🏥 Medicare Breakdown: understanding what’s covered, what’s not, and what it really costs
💳 HSA Benefits: how Health Savings Accounts create powerful long-term tax advantages
📈 Smart Strategies: practical ways to manage and reduce future healthcare costs
 
Fidelity Investments® Releases 2025 Retiree Health Care Cost Estimate:
https://newsroom.fidelity.com/pressreleases/fidelity-investments--releases-2025-retiree-health-care-cost-estimate--a-timely-reminder-for-all-gen/s/3c62e988-12e2-4dc8-afb4-f44b06c6d52e 
 
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.

Retirement Planning Quiz: How Ready Are You?

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
Think you’re ready for retirement? Let’s find out. Today, we’ll put you in the hot seat with a rapid-fire retirement quiz. Five questions. Multiple choice. Real-world consequences. Social Security timing, IRA limits, and RMD rules aren’t just trivia—they’re decisions that can make or break your financial future.
Along the way, Wade explains why so many people miss the mark, clears up common misconceptions, and shows how a simple rule of thumb like the 4% rule can backfire if you don’t have a customized plan. So grab a pen, keep score, and see how you measure up. If you don’t ace this quiz, don’t worry—you’ll walk away with clear action steps to boost your retirement readiness and confidence.
Here’s some of what we discuss in this episode:
🧠 Test your retirement knowledge with 5 key questions
🕰️ Why Social Security timing is critical
📈 IRA contribution limits for 2025 explained
📑 Which accounts require RMDs (and which don’t)
⚠️ The biggest risks retirees must prepare for
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.

The Hidden Medicare Penalty You Might Be Paying

📞✨ 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.

The 4 Things You Can Control in Retirement

📞✨ 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.