The Money Knight

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ 
Nobody enjoys tax season, but retirement introduces a whole new set of rules, and many retirees don’t realize the impact until it’s too late. In this episode, Wade breaks down some of the most common tax mistakes new retirees make and explains why tax planning shouldn’t be treated as a once-a-year task, but as a strategy that works for the next decade and beyond.
Later in the episode, Wade answers listener questions, offering insights on common retirement challenges- like whether to keep heavily concentrated stock in a 401(k) and how to manage taxes on an inherited IRA.
Here’s some of what we discuss in this episode:
💣 RMD Time Bomb: Future withdrawals can create massive tax hits
🔁 Roth Strategy: Conversions must be timed and coordinated carefully
💸 Social Security Taxes: Benefits can be more taxable than expected
🧮 Short vs Long-Term: Tax prep isn’t the same as tax planning
‍❤️ Survivor Impact: Taxes often rise after one spouse passes
Read The 5 Biggest Tax Mistakes New Retirees Make in the First 5 Years
https://www.kiplinger.com/taxes/tax-planning/biggest-tax-mistakes-new-retirees-make-in-first-years
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/ 
There’s no shortage of financial advice out there and unfortunately, not all of it is good. Some of the most damaging retirement mistakes don’t come from reckless behavior. They come from myths that sound reasonable, get repeated often, and quietly work their way into your planning decisions. Wade breaks down some of the most common retirement myths and explains why believing them can quietly wreck your long-term strategy, and what to do instead.
For this week’s Kingdom Minute, Wade shares the story of Elisha and the widow from 2 Kings to illustrate how God often uses what we already have, however small, as the basis for His provision.
Here’s some of what we discuss in this episode:
📘 Bigger Plan Better?: Thick binders don’t equal clarity
📜 Just A Will?: Simple estates still need key documents
💔 Half Income Myth: Surviving spouse needs far more
🏦 Social Security Reliance: It’s a foundation, not full income
💵 Lower Taxes Assumption: Retirement brackets may surprise you
 
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/ 
New government-backed savings accounts for kids are coming, and on the surface, they sound like a win. The Trump Accounts promise $1,000 in free money for eligible newborns, long-term investing, and a potential financial head start. But once you look under the hood, important questions emerge. In this episode, Wade breaks down what we know so far, the pros and cons, and how these new accounts might fit — or not fit — into your family’s long-term strategy.
Here’s some of what we discuss in this episode:
💵 Free Money Window: $1,000 for eligible newborns
⚖️ Pros and Trade-Offs: Simple setup but tax implications
📊 Account Comparisons: 529s, Roths, and UTMAs
🏢 Private Sector Support: Employers and donors may contribute
 
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 year often brings small changes that quietly add up. In this episode, Wade walks through what’s different in 2026 for retirees and those approaching retirement and why paying attention early matters. From income adjustments to planning opportunities, these shifts can affect cash flow, taxes, and long-term strategy.
For this week’s Kingdom Minute, we talk about how the Bible emphasizes daily faithfulness and trust in God over frantic New Year reinvention, reminding us that God’s mercies are new every morning.
Here’s some of what we discuss in this episode:
📈 Social Security Updates: How cost-of-living changes affect income
🏥 Medicare Costs: Why healthcare expenses continue to rise
🧾 Senior Tax Breaks: New deductions and planning considerations
⏳ Catch-Up Opportunities: Expanded ways to boost retirement savings
💳 Debt Decisions: How planning changes after debt is gone
 
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/ 
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.

📞✨ 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.

📞✨ 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.

📞✨ 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.

📞✨ 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.

📞✨ 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.