The Money Knight

Hosted by Wade Chessman

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162

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Jun 2026

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About the show

Financial and retirement guidance from CERTIFIED FINANCIAL PLANNER™ professional Wade Chessman, President, Wealth Advisor of Chessman Wealth Strategies in the Dallas, Texas area. Wade is the author of Giving Transforms You and hosts this podcast to help you better prepare for your financial future and to retire with financial confidence. Investment advisory services offered through CWM, LLC, an SEC Registered Investment Advisor. Carson Partners, a division of CWM, LLC, is a nationwide partnership of advisors. 7557 Rambler Road, Suite 1010, Dallas, TX 75231. 214-572-2120.

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June 4, 2026Episode 16417 min

How Scammers Target Retirees and How to Fight Back

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ Financial scams are becoming more sophisticated, more believable, and more expensive than ever before. With artificial intelligence, fake voices, spoofed phone numbers, and convincing emails, today's scammers have more tools than ever to target retirees and steal hard-earned savings. Wade breaks down some of the most common scams affecting retirees and provides practical ways to protect yourself. For this week’s Kingdom Minute, Wade talks about how protecting yourself from scams is part of biblical stewardship. He cites passages from scripture to stress slowing down, avoiding get‑rich‑quick schemes, watching out for “wolves in sheep’s clothing,” and seeking wise counsel before making financial decisions. Here’s some of what we discuss in this episode: 📈 Investment Fraud: Crypto schemes and fake returns 🏛️ Government Impersonators: IRS, Medicare, and Social Security scams ❤️ Romance Scams: Emotional manipulation and financial theft 💻 Tech Support Fraud: Fake alerts and computer access tricks 🛡️ Protection Strategies: Slowing down and verifying everything 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.

May 21, 2026Episode 16317 min

You've Managed Your Own Money Successfully - Why Would You Need an Advisor Now?

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ You’ve spent decades saving, investing, and managing your money responsibly. So why would you suddenly need a financial advisor right before retirement? In this episode, Wade tackles that exact question from a listener who’s done well investing on their own but is hesitant to “turn everything over” to an advisor. In this week’s Kingdom Minute, Wade explores Jesus’ command to “render unto Caesar” and what it teaches us about stewardship, ownership, and where our ultimate trust belongs. Here’s some of what we discuss in this episode: 💰 Why accumulating wealth and living off wealth require different skill sets ⚠️ The costly retirement mistakes that are harder to recover from 🧾 Tax planning, Social Security, Medicare & RMD complexities 🤝 Why working with an advisor doesn’t mean losing control 🏌️ Wade’s golf analogy for how one bad financial decision can derail retirement 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.

May 7, 2026Episode 16215 min

What Golf Teaches Us About Financial Planning

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ At first glance, golf and financial planning don’t seem to have much in common, but look a little closer, and the parallels are hard to ignore. In this episode, Wade breaks down how certain concepts on the golf course translate directly into smarter financial decisions. It’s a fresh way to think about building a plan that actually works over time. Here’s some of what we discuss in this episode: ⛳ Hole-in-One: Luck won’t drive long-term success 🎯 Stay Consistent: Methodical play wins over time 🧰 Right Tools Matter: Use diverse investment strategies 🧭 Trust Your Guide: Expert advice improves outcomes 🏌️ Pro Lessons: Stick with one clear strategy 🏁 Finish Strong: Stay focused on the long game 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.

April 16, 2026Episode 16116 min

From Zero Savings to a 3 Million-Dollar Exit

📞✨ Get in touch with Chessman Wealth: https://www.chessmanwealth.com/ Going from little to no retirement savings to a multi-million-dollar windfall sounds like a dream, but it comes with a whole new set of challenges. And one wrong move early on can have long-term consequences. Today, Wade walks through what to do after a major liquidity event, including how to handle taxes, define what “enough” really means, and avoid costly mistakes. For this week’s Kingdom Minute, Wade shares how monks pursued economic sufficiency, not false security. This meant having just enough, rejecting the love of money, consuming less than they received, and using surplus for hospitality and generosity. Here’s some of what we discuss in this episode: 💰 Lump Sum Reality: $3M isn’t $3M after taxes, understand your true net 🧾 Tax Planning First: Structure and timing can significantly impact what you keep ⏳ Don’t Rush Decisions: Park money safely and avoid emotional or impulsive moves 🎯 Define “Enough”: Your lifestyle, not the number, determines success 📊 Smart Risk Strategy: Diversification beats swinging for the fences ⚠️ Avoid Big Mistakes: Don’t chase deals, loans, or “opportunities” without a plan 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.

April 2, 2026Episode 16014 min

Tax Mistakes New Retirees Make

📞✨ 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.

March 19, 2026Episode 15918 min

Financial Myths That Can Quietly Wreck a Retirement Plan

📞✨ 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.

March 5, 2026Episode 15813 min

Trump Accounts: Free Money or Future Headache?

📞✨ 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.

February 19, 2026Episode 15715 min

What’s Different About 2026 for Retirees and Pre-Retirees

📞✨ 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.

February 5, 2026Episode 1568 min

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.

January 15, 2026Episode 15412 min

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.