- 17
- Episodes
- Daily
- Cadence
- 2026
- First episode
About Tax Smart Retirement Podcast
Welcome to The Tax-Smart Retirement Podcast, the go-to podcast for anyone looking to take charge of their financial future. Hosted by Charles Winfrey of The Rollover Company, each episode dives into the essentials of 401(k) planning, lump-sum pensions, and IRAs with straightforward information and practical advice. Charles brings his experience as a financial advisor to the mic, making complex topics easy to understand for listeners at any stage of their financial journey. Tune in to each new episode of The Tax-Smart Retirement Podcast for lively discussion packed with real-world tips and professional insights that will help you make smarter decisions and roll over your financial concerns into confidence!
- Publisher
- Charles Winfrey
- Category
- business · education
- Language
- en
- Explicit
- No
- First episode
- 15 Jun 2026
- Latest episode
- 29 Sept 2026
Latest episodes
17 episodes in the feed.
29 Sept 2026
Think You’re Ready for Retirement? The Numbers May Say Otherwise
Is a $1 million retirement account really enough, or could the math tell a different story? In this episode, Charles Winfrey explores the gap between retirement confidence and retirement readiness. He discusses why retirement is no longer defined by a single age, how Social Security, healthcare, taxes, and income planning work together, and why focusing on an account balance alone can create blind spots. The conversation also covers the risks of letting political headlines influence long-term financial decisions and the importance of building a retirement strategy around personal goals instead of predictions. A thoughtful look at creating a retirement plan designed for life's many transitions. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
22 Sept 2026
The Retirement Grab Bars Most People Ignore
The biggest threats to your retirement plan may be the boring details you’ve been ignoring. This episode explores the “grab bars” of retirement planning, including beneficiary reviews, Roth conversions, account coordination, healthcare planning, and long-term care strategies. Charles Winfrey also breaks down the Social Security claiming debate, explaining why the mathematically optimal answer is not always the best personal decision. Plus, a look at why annuities are back in the spotlight, how guaranteed income fits into a retirement strategy, and why every financial tool should have a specific job. Learn how coordinating taxes, income, investments, healthcare, and estate planning can help create a more complete retirement plan. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
15 Sept 2026
Before You Spend That Windfall, Ask Yourself This One Question
A surprise inheritance, bonus, or windfall can feel like freedom, but the wrong first move could create long-term financial challenges. Charles discusses why sudden wealth should be viewed through the lens of a retirement plan, not impulse spending. He explores lifestyle creep, retirement income sustainability, taxes, Medicare costs, and the importance of budgeting for family support without jeopardizing your own future. The conversation also covers how retirees can evaluate life insurance policies as their needs evolve, why beneficiary reviews matter, and how planning can help align spending, legacy goals, and long-term financial security. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
1 Sept 2026
Are You Sacrificing Retirement to Pay for College?
Could helping your child pay for college put your own retirement at risk? This episode explores the difficult balance between supporting family goals and protecting long-term financial security. Charles Winfrey discusses why parents should evaluate retirement readiness before tapping savings for tuition, the hidden risks of market complacency as retirement approaches, and how a three-basket strategy can help manage income, growth, and unexpected expenses. The conversation also covers retirement lifestyle planning, inflation, healthcare costs, tax uncertainty, and the importance of ongoing reviews to help keep a retirement plan aligned with changing needs and goals. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
25 Aug 2026
The Retirement Costs Most People Never See Coming
What if the biggest threat to your retirement is the cost you never saw coming? In this episode, Charles compares retirement planning to car ownership, where the true expenses go far beyond the monthly payment. He discusses hidden retirement costs, healthcare expenses, inflation, tax diversification, sequence of returns risk, and why a retirement account is not the same as a retirement income plan. Learn how the "three-bucket" approach for cash, income, and growth can help create flexibility when markets, taxes, and life's surprises change the road ahead. It's a practical conversation about building a retirement strategy designed for the realities of long-term financial independence. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
18 Aug 2026
Could Your Dream Retirement Move Become an Expensive Mistake?
What if the move that looks cheaper on paper ends up costing you more in retirement? This episode explores three decisions that can have lasting financial consequences: relocating for a lower cost of living, delaying retirement because of the "one more year" mindset, and managing unexpected windfalls such as inheritances. Charles Winfrey discusses how healthcare, taxes, family proximity, retirement timing, and tax planning can all influence outcomes beyond the headlines. He also examines the inherited IRA rules that can create unexpected tax challenges for beneficiaries and why evaluating the full picture matters before making a major financial decision. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
11 Aug 2026
The Retirement Mistakes That Cost More Than Expected
One overlooked retirement expense can quietly unravel even the most carefully built plan. In this episode, Charles discusses common retirement pitfalls, including healthcare coverage gaps before Medicare, unexpected expenses, Social Security taxation, and the ripple effects of RMD decisions. He explores why retirement planning involves more than investments alone and discuss the role of income, tax, healthcare, and estate strategies. The conversation also covers the growing use of AI in retirement planning, the importance of personal context, and common misconceptions about annuities. Plus, learn how seemingly simple financial decisions can trigger unexpected tax and Medicare consequences years later. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
4 Aug 2026
The Retirement Rules That May Be Costing You More Than You Think
The retirement rules that worked decades ago may be creating hidden risks today. In this episode, Charles Winfrey examines common retirement assumptions from the 4% rule and relying on home equity to overlooking longevity risk and phantom income. He discusses how taxes, fees, RMDs, Medicare premiums, and Social Security taxation can affect retirement cash flow, why living longer changes the planning equation, and how Roth conversion strategies may fit into a broader retirement approach. The conversation focuses on building a retirement income plan that accounts for spending needs, tax efficiency, and long-term financial sustainability. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
28 Jul 2026
Can AI Build Your Retirement Plan, Or Is It Missing the Most Important Part?
What happens when retirement arrives before you're ready, or when AI starts giving financial answers faster than people can? In this episode, Charles Winfrey explores the challenges of unexpected retirement, including Social Security timing, healthcare gaps before Medicare, and creating an income plan that can adapt to real life. He also discusses where artificial intelligence fits into financial planning, why technology can help with calculations but not personal judgment, and the importance of balancing spending, savings, and long-term goals. Plus, learn how the first five years of retirement can shape decades of financial decisions and why having a plan matters as much as building your nest egg. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
21 Jul 2026
The Retirement Tax Trap Most Families Never See Coming
Could a hidden tax trap, overlooked fees, or the wrong income strategy quietly reshape your retirement? In this episode of the TaxSmart Retirement Show, Charles Winfrey breaks down how to replace your paycheck with sustainable retirement income, why lifestyle, not income labels, matters most, and the common annuity mistakes that can cost retirees thousands. He also explores Roth conversion strategies, changing tax laws, and the little-known “widow’s penalty” that can increase taxes and Medicare costs for surviving spouses. Learn practical ways to evaluate retirement expenses, reduce unnecessary fees, and build a tax-aware income plan designed to adapt over time. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
14 Jul 2026
What If Your “Affordable” Retirement Move Ends Up Costing More?
Could chasing a cheaper retirement dream actually cost you more? In this episode, Charles Winfrey unpacks the hidden expenses that can derail retirement plans, from relocating to a “best places to retire” destination to working one more year when the numbers may not require it. He explores how healthcare access, taxes, family proximity, and quality of life can outweigh lower housing costs. The conversation also highlights the tax surprises that can accompany inheritances, IRA distributions, and other financial windfalls. Learn why stress-testing major retirement decisions and understanding the full financial picture may be more important than following popular lists or rules of thumb Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
30 Jun 2026
Why Planning Backward Might Be the Smarter Route to Retirement
What if planning forward is the wrong way to retire? This episode flips the script on traditional retirement planning by exploring a “reverse engineering” approach, starting with your end goal and working backward to build a strategy. The conversation breaks down why relying on investments alone can miss key factors, and how taxes, income timing, healthcare, and estate planning all intersect. It also tackles common misconceptions about lower taxes in retirement, the risks of stacked income streams, and why Roth conversion decisions go beyond simple calculators. The focus stays on building a comprehensive plan that aligns with real-life goals, not just numbers on a page. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
23 Jun 2026
From Layoffs to Tax Wins: The Retirement Playbook You Need
What happens when life throws a curveball right before retirement? Charles Winfrey breaks down practical strategies to stay on track, whether you’re facing a sudden layoff, questioning your readiness, or looking to maximize your long-term tax efficiency. This episode explores how to realistically assess your financial position, avoid costly mistakes during income gaps, and use tools like Roth conversions to create more control over your retirement income. From stress-testing your plan to identifying smart tax opportunities, you’ll walk away with a clearer framework for making confident, informed decisions about your future. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
15 Jun 2026
Social Security Secrets: What You Need to Know Before Retirement
Social Security is evolving and understanding how it works today is critical for your retirement future. In this episode, Charles Winfrey breaks down the current state of Social Security, including the financial pressures facing the system and what they could mean for future benefits. Learn how taxes can impact your Social Security income, why up to 85% of benefits may be taxable depending on your total income, and how smart planning can help you keep more of what you earn. Charles also shares practical strategies to help you make informed claiming decisions, manage income streams, and build a more resilient retirement plan in an uncertain economic landscape. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
15 Jun 2026
From Paycheck to Paycheck… to Retirement: Are You Really Ready?
What happens when the paycheck stops, but life doesn’t? In this episode, Charles Winfrey of The Rollover Company breaks down the realities of retirement planning beyond just saving money. With decades of experience helping pre-retirees and retirees, Winfrey explains why building a sustainable income strategy is critical to maintaining your lifestyle. From navigating taxes and healthcare costs to creating reliable income streams, this conversation highlights the importance of a comprehensive, evolving financial plan. You’ll also hear how a family-oriented approach to advising builds trust and clarity during major life transitions. If you’ve ever wondered how to turn your savings into a lasting retirement paycheck, this episode offers practical perspective on planning smarter for the future. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
15 Jun 2026
Stop Overpaying the IRS: Smart Tax Moves for Retirement, Athletes & Your Legacy
Tax planning isn’t one-size-fits-all, especially when retirement, athletic careers, and legacy goals collide. In this episode, Charles Winfrey breaks down how proactive tax strategies can help retirees preserve income, athletes manage short high-earning windows, and families protect wealth for future generations. From navigating required distributions and Social Security taxes to structuring income and beneficiary designations, the conversation highlights why timing, strategy, and long-term planning matter. The episode also explores how thoughtful legacy planning can reduce tax burdens and ensure assets transfer efficiently. Whether you’re planning for retirement, managing peak earnings, or thinking about what you’ll leave behind, this discussion offers a clear look at smarter ways to control your tax story. Hear The Tax Smart Retirement show every Sunday at 6am WAMJ 107.5/97.5 Powered by The Rollover Company. For more information and to schedule a complimentary consultation with Charles Winfrey, visit www.Rollovercompany.com (http://www.Rollovercompany.com). See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
15 Jun 2026
Tax Smart Retirement Podcast Trailer
Welcome to The Tax-Smart Retirement Podcast, the go-to podcast for anyone looking to take charge of their financial future. Hosted by Charles Winfrey of The Rollover Company, each episode dives into the essentials of 401(k) planning, lump-sum pensions, and IRAs with straightforward information and practical advice. Charles brings his experience as a financial advisor to the mic, making complex topics easy to understand for listeners at any stage of their financial journey. Tune in to each new episode of Tax-Smart Retirement Podcast for lively discussion packed with real-world tips and professional insights that will help you make smarter decisions and roll over your financial concerns into confidence! See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
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