Episodes

  • The Social Security Timing Puzzle: Claim Early or Wait and Risk Six-Figure Mistakes

    The Social Security Timing Puzzle: Claim Early or Wait and Risk Six-Figure Mistakes
    May 10 2026
    Most people spend more time picking a TV than deciding when to take Social Security… but that one decision could impact your retirement income by six figures or more.
    In this week’s episode of Retirement Success, Steve and Elizabeth Holland break down the Social Security timing puzzle and discuss:

    ✅ Why claiming Social Security at 62 vs. waiting until 70 can drastically change your lifetime income
    ✅ How the 8% annual increase after full retirement age actually works
    ✅ Why there is no “one-size-fits-all” claiming strategy
    ✅ The importance of spousal coordination in maximizing household benefits
    ✅ How longevity and break-even age factor into the decision
    ✅ Why market risk and withdrawals can impact early retirement timing
    ✅ Common mistakes people make when making Social Security decisions in isolation

    If you’ve ever wondered:
    ➡️ “Am I taking Social Security too early?”
    ➡️ “Should I wait until 70 or start now?”
    ➡️ “How does this fit into my overall retirement plan?”

    This episode is for you.


    📞 Call today for a complimentary retirement income review: 727-228-6449
    🌐 askthehollands.com

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    53 mins
  • What happens when your 401(k) becomes your paycheck in retirement?

    What happens when your 401(k) becomes your paycheck in retirement?
    May 10 2026
    In this episode of Retirement Success, Steve and Elizabeth Holland break down one of the biggest retirement realities facing Americans today: only a small percentage of workers still have traditional pensions — meaning your retirement income strategy matters more than ever.

    Steve, Elizabeth, and Todd MJ Schmidt discuss:
    ✔️ The biggest mistakes people make with their 401(k)s
    ✔️ Why retirement requires a completely different strategy than accumulation years
    ✔️ Sequence of returns risk and how market downturns can permanently impact retirement income
    ✔️ How taxes, inflation, and required minimum distributions (RMDs) affect your future
    ✔️ The importance of creating a sustainable income plan
    ✔️ Why “a million dollars” in a 401(k) may not actually be yours after taxes
    ✔️ How to create your own personal pension strategy
    ✔️ The role of tax planning in retirement success
    ✔️ Real-life retirement concerns including divorce, widowhood, downsizing, and lifestyle spending

    The Holland Group Retirement Wealth Advisors explains why retirement planning is about more than investing — it’s about building a strategy designed to protect your lifestyle for decades to come.

    📞 Schedule your complimentary retirement income review today: 727-228-6449

    🌐 Visit: askthehollands.com
    📺 Watch Retirement Success Sundays at 11:30 AM on Channel 10.
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    53 mins
  • The New Retirement Reality: Planning for Longevity, Taxes & Income

    The New Retirement Reality: Planning for Longevity, Taxes & Income
    Apr 19 2026
    This episode of Retirement Success features Steve and Elizabeth Holland of The Holland Group Retirement Wealth Advisors as they dive into what can only be described as the new retirement reality.

    People are living longer than ever—and while that sounds like great news, it also means your retirement savings now need to last 25, 30, or even 40 years. In this episode, the Hollands break down why longevity is both a blessing and a financial risk, and how outdated retirement strategies can leave you vulnerable in today’s environment.

    From longevity risk and rising healthcare costs to Social Security timing and tax-efficient withdrawal strategies, this conversation highlights the real challenges retirees face—and how to plan for them the right way.

    If you want to make sure you don’t outlive your money and avoid costly financial missteps, this is an episode you don’t want to miss.

    •The New Retirement Reality: Why retirement is no longer 10–15 years—and how longer lifespans are changing everything about financial planning.
    •Longevity Risk Explained: The #1 fear retirees face—outliving their money—and why this concern affects everyone, regardless of portfolio size.
    •The Social Security Gap: Why Social Security typically replaces only about 40% of your income—and how that leaves a major gap you must plan for.
    •Timing Matters: How claiming Social Security too early can permanently reduce your benefits—and why delaying could significantly increase your lifetime income.
    •The Hidden Impact of Taxes: Why taxes can quietly erode your retirement savings—and how poor withdrawal strategies can cost you 20–30% more than necessary.
    •Sequence of Returns Risk: Why market downturns early in retirement can have long-term consequences—even if the market eventually recovers.
    •Healthcare & Inflation Pressures: How rising costs can reduce your purchasing power over time—and why planning for these expenses is critical.
    •The Power of Income Planning: How structuring your retirement into income segments can help create stability, flexibility, and long-term sustainability.
    •Avoiding Emotional Decisions: Why having a clear, structured plan helps you stay on track—even during market volatility.
    •Turning Longevity Into Opportunity: How the right strategy allows you to enjoy more time with family, travel, and experiences—without financial stress.

    If you’ve been planning for retirement based on outdated assumptions, now is the time to rethink your strategy. This episode will help you build a plan designed not just to get you to retirement—but to carry you through it with confidence.
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    53 mins
  • The “Healthcare Heist”: How Medical Costs & Long-Term Care Can Quietly Derail Your Retirement

    The “Healthcare Heist”: How Medical Costs & Long-Term Care Can Quietly Derail Your Retirement
    Apr 19 2026
    Hosted by Todd “MJ” Schmidt, this episode of Retirement Success features Steve and Elizabeth Holland of The Holland Group Retirement Wealth Advisors as they uncover one of the most underestimated threats to your retirement plan—healthcare costs.

    While many retirees focus on market performance and investment returns, far fewer prepare for the rising and often unpredictable cost of healthcare. In this episode, the Hollands explain why healthcare is the “silent thief” that can quietly erode your savings—and how proper planning can help you stay protected.

    From breaking down the true cost of healthcare in retirement to navigating Medicare decisions and long-term care strategies, this conversation turns complex topics into clear, actionable insights. If you want to avoid costly surprises and build a retirement plan that truly lasts, this episode is a must-listen.
    • Why Healthcare Is the Real Retirement Risk: Why healthcare—not market volatility—is often the biggest threat to your financial future.
    • The True Cost of Retirement Healthcare: How a typical retired couple may need over $170,000—and why that number feels less overwhelming when properly planned
    • Breaking Down the “Healthcare Iceberg”: Understanding how small, ongoing costs add up over time instead of hitting all at once.
    • Medicare Decisions That Matter: The difference between paying more now vs. risking higher costs later—and how timing impacts lifelong penalties.
    • The Long-Term Care Reality: Why 70% of retirees will need some form of long-term care—and how costs can exceed $10,000 per month.
    • The Emotional & Financial Impact: How lack of planning can affect not just your finances—but your spouse and family as well.
    • Smarter Long-Term Care Strategies: How hybrid policies can provide coverage while still protecting your legacy if care isn’t needed.
    • The Power of a Written Plan: Why “guessing” isn’t a strategy—and how a structured retirement plan can help you prepare for the unexpected.
    • Hidden Tax Advantages in Healthcare Planning: How tools like Health Savings Accounts (HSAs) can provide powerful tax benefits when used correctly.
    • Why Most Plans Fall Short: The common gaps in retirement plans—and how overlooking healthcare can put everything at risk.

    If you’ve spent years building your retirement savings but haven’t planned for healthcare costs, you could be leaving your future exposed. This episode shows you how to take control, reduce uncertainty, and build a retirement plan that accounts for life’s biggest unknowns.

    📞 Have questions or want a second opinion? Call: 727-228-6449
    🌐 Learn more or schedule a discovery call: https://askthehollands.com
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    54 mins
  • How to Create Tax-Free Income in Retirement (and Avoid Costly Tax Mistakes)

    How to Create Tax-Free Income in Retirement (and Avoid Costly Tax Mistakes)
    Apr 5 2026
    Hosted by Todd “MJ” Schmidt, this episode of Retirement Success features Steve and Elizabeth Holland of The Holland Group Retirement Wealth Advisors as they break down one of the most overlooked—but most important—parts of retirement planning: TAXES.

    While many retirees focus on growing their savings, far fewer understand how taxes can significantly impact how much of that money they actually get to keep. In this episode, the Hollands explain why taxes may be your biggest expense in retirement—and how creating tax-free income streams can help protect your wealth, reduce long-term tax liability, and give you more control over your financial future. From Roth IRA strategies and Roth conversions to Required Minimum Distributions (RMDs), Social Security taxation, and Medicare premium surprises, this conversation simplifies complex topics into real, actionable insights. If you want to keep more of your hard-earned money and avoid costly mistakes, this episode is a must-listen.
    • Why Taxes Matter More Than Ever: How taxes can become your largest expense in retirement—and why most people underestimate their long-term impact.
    • The Power of Tax-Free Income: Why Roth IRAs and tax-free strategies are so valuable—and how paying taxes now could save you significantly in the future.
    • Roth Conversions Made Simple: A clear breakdown of how converting from tax-deferred accounts to tax-free accounts works—and why timing and strategy are critical.
    • The “Tax Time Bomb” Problem: Why having 70–90% of your savings in tax-deferred accounts (like IRAs and 401(k)s) could expose you to higher taxes later.
    • Big Mistakes to Avoid: From paying taxes the wrong way to converting too much at once, the Hollands explain common pitfalls that can cost you thousands over time.
    • RMDs and Hidden Tax Traps: How Required Minimum Distributions can push you into higher tax brackets—and what you can do to plan ahead.
    • Social Security & Medicare Surprises: Why up to 85% of your Social Security can be taxed—and how poor planning can increase your Medicare premiums (IRMAA).
    • Why Tax Planning Isn’t Optional: The difference between tax preparation and proactive tax planning—and why a long-term strategy is essential for retirement success.
    • Building a Complete Retirement Plan: Why your investment strategy and tax strategy must work together to create sustainable, predictable income in retirement.
    If you’ve spent years building your retirement savings but haven’t built a strategy to manage taxes, you could be leaving a significant portion of your wealth at risk. This episode shows you how to take control, reduce your tax burden, and create a more secure, tax-efficient retirement.
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    54 mins
  • How to Protect Your Retirement in Times of Economic and Political Uncertainty

    How to Protect Your Retirement in Times of Economic and Political Uncertainty
    Mar 21 2026
    Welcome back to Retirement Success with Steve and Elizabeth Holland and Todd "MJ" Schnitt. For over 30 years, The Holland Group Retirement Wealth Advisors have been dedicated to helping you build inflation-adjusted, tax-advantaged, customized plans for a secure retirement. In this episode, we focuse on one of the biggest concerns facing individuals today: how ongoing political chaos, economic instability, and global uncertainty can impact retirement. With constant headlines creating fear and confusion, many people are left asking the same question- what does all of this mean for my financial future?

    We highlights the importance of taking control of your retirement planning instead of leaving it to chance. Featuring insights on working with trusted advisors like Steve and Elizabeth Holland of The Holland Group Retirement Wealth Advisors, this episode emphasizes the value of having a clear, personalized strategy designed to navigate uncertain times.

    Rather than relying on generic advice, the conversation centers on building a retirement plan that protects your hard-earned savings and prepares you for whatever the future may bring. With the right guidance, you can move forward with confidence, even in an unpredictable world.

    • Facing Today’s Uncertainty: Why constant news about political and economic instability is causing anxiety for those planning for retirement—and what you can do about it.

    • The Risk of Doing Nothing: How leaving your financial future to chance can impact your long-term security, especially during volatile times.

    • Building a Retirement Plan That Lasts: The importance of creating a strategy designed to withstand market fluctuations and economic shifts.

    • Personalized vs. Generic Advice: Why cookie-cutter financial solutions fall short—and how tailored planning can better support your retirement goals.

    • The Value of Trusted Guidance: How working with experienced advisors can help you protect your assets, stay focused, and make confident financial decisions.

    If you’re thinking about retirement and feeling uncertain about the future, this episode offers a timely reminder: the right plan and the right people can help you stay on track no matter what’s happening in the world.

    Contact The Holland Group Retirement Wealth Advisors for a complimentary, no-obligation review by calling (727) 228-6449, or visit AskTheHollands.com to schedule a discovery call at your convenience.
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    53 mins
  • The Ghostwriter Trap: Why Your "Free" Will Could Be a Costly Nightmare

    The Ghostwriter Trap: Why Your "Free" Will Could Be a Costly Nightmare
    Mar 16 2026
    In this episode of Retirement Success, MJ Schnitt joins Steve and Elizabeth Hollandof The Holland Group Retirement Wealth Advisors as they pull back the curtain on a dangerous trend in estate planning: the "ghostwritten" will. While the allure of free or cheap do-it-yourself online documents is growing, the Hollands explain why these "cookie-cutter" solutions often fail when families need them most.
    The team discusses the critical difference between a generic template and a plan built through a face-to-face conversation with an attorney who understands your specific life savings and family dynamics. They also share cautionary tales of how improper documentation can lead to expensive legal battles, especially in the era of "blended families".
    Key Highlights Include:
    • The "Incapacity Gap": Learn why a will is "useless" until the moment of death and how a lack of proper durable power of attorney can force families into expensive, court-appointed guardianship proceedings if you become ill or injured.
    • The Funding Failure: Steve and Elizabeth reveal a common mistake—having a trust but failing to actually "fund" it by transferring assets into it. Without this step, your estate could still end up in a lengthy and public probate process.
    • Asset Protection Blind Spots: Discover why a standard revocable living trust offers "zero" creditor-proofing during your lifetime and what specific language is required to protect inherited wealth for the next generation.
    • The High Cost of "Free": The Hollands break down why financial firms offering free wills as a "gift" can actually create massive liabilities, including documents that aren't state-specific or valid under Florida law.
    • Personal Lessons in Legacy: Steve shares a moving personal story about his own father's estate, illustrating how a "heartless" second spouse and a late-stage will change can lead to the loss of precious family heirlooms and years of drama.
    Contact The Holland Group Retirement Wealth Advisors for a complimentary, no-obligation review by calling (727) 228-6449, or visit AskTheHollands.com to schedule a discovery call at your convenience. Ready to see if your plan is built to last?
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    53 mins
  • Why You Need a Retirement Plan During Uncertain Economic and Political Times

    Why You Need a Retirement Plan During Uncertain Economic and Political Times
    Mar 14 2026
    Hosted by Glenn Beck, this episode highlights the growing concerns many people have about their financial future as global uncertainty continues to dominate the news. With constant headlines about political turmoil, economic instability, and an unpredictable market, many are left wondering how these changes could affect their retirement plans. Glenn emphasizes the importance of having a solid, personalized retirement strategy rather than leaving your financial future to chance.

    Joined by Steve and Elizabeth Holland of The Holland Group Retirement Wealth Advisors, the discussion focuses on how individuals approaching retirement can better protect the wealth they’ve worked hard to build. Instead of relying on generic financial advice or one-size-fits-all solutions, the Hollands emphasize building retirement strategies designed to withstand changing market conditions and economic uncertainty.

    In this episode, listeners will learn why preparation, planning, and trusted financial guidance can make the difference between feeling uncertain about retirement and having confidence in the years ahead.

    - Navigating Uncertain Times: Why today’s political and economic headlines are causing many people to rethink their retirement plans—and why ignoring the uncertainty can be risky.

    - Why Retirement Planning Matters More Than Ever: How market volatility, inflation concerns, and global instability can impact long-term financial security if a clear retirement strategy isn’t in place.

    - Protecting What You’ve Built: Steve and Elizabeth Holland explain the importance of safeguarding retirement savings and creating a financial plan designed to weather unpredictable market cycles.

    - Beyond Cookie-Cutter Advice: Why personalized retirement strategies are essential—and how tailored planning can help align investments with long-term retirement goals.

    - Working With a Trusted Advisor: The value of having experienced professionals guide you through complex financial decisions, helping you stay focused on long-term security rather than short-term headlines.

    If you’re approaching retirement or simply want to feel more confident about your financial future, this episode offers valuable insights into building a plan designed to withstand uncertainty while protecting the wealth you’ve worked so hard to achieve.

    Contact The Holland Group Retirement Wealth Advisors for a complimentary, no-obligation review by calling (727) 228-6449, or visit AskTheHollands.com to schedule a discovery call at your convenience.
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    53 mins