Episodes

  • What We’ve Learned From 150 Years of Stock Market Crashes

    What We’ve Learned From 150 Years of Stock Market Crashes
    Apr 14 2025

    It’s no secret that market volatility can feel especially nerve-wracking when you’re no longer earning a paycheck.

    But what if I told you that, historically, every single crash has ended the same way—with a recovery?

    That's what happened after the Covid-19 market crash, the 2021 downturn, and even the Great Depression.

    We're going to discuss an article titled "What We’ve Learned From 150 Years of Stock Market Crashes" by Emelia Fredlick. The article highlights some of the worst market downturns in history and, more importantly, the lessons they offer for long-term investors like you.

    Takeaways:

    Lesson #1: We Can’t Predict Recovery Times
    Lesson #2: Every Decade Brings a Market Crash
    Lesson #3: Staying Invested is the Only Winning Strategy

    Then I answer question sent in from a listener: "What are some good ways to gift money to my children while I'm still living?"

    All of this in less than 20 minutes.

    Resources:

    • MorningStar article by Emelia Fredlick: What We’ve Learned From 150 Years of Stock Market Crashes
    • Book by Bill Perkins: Die With Zero
    • How many annual exclusions are available? IRS website on Gift Taxes

    Connect with Benjamin Brandt
    • Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
    • Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter
    • Work with Benjamin: https://retirementstartstoday.com/start

    Get the book - out now!
    Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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    19 mins
  • How To Protect Your 401(k) from a Stock Market Crash

    How To Protect Your 401(k) from a Stock Market Crash
    Apr 7 2025

    Is your 401(k) prepared for a market crash? With market volatility on the rise, many investors are wondering how to protect their portfolios.

    In this episode, I share an article from Go Banking Rates on how to safeguard your retirement savings during turbulent times. I’ll highlight key takeaways from the article, share my own insights on where I agree or disagree, and explain why certain strategies may be more effective than others.

    After that, I answer a listener’s question about long-term care (LTC) insurance. We’ll explore different types of LTC policies, discuss the ideal time to purchase coverage (such as around age 50), and consider whether self-funding might be a smarter financial strategy.

    Key takeaways:

    • Diversify, Diversify, Diversify
    • Shift Toward Conservative Investments as You Near Retirement
    • Rebalance Regularly—Not Just After a Crash
    • Consider a 401(k) Rollover for More Flexibility
    • Stay the Course—Don't Panic Sell

    Resources:

    Go Banking Rates article: How To Protect Your 401(k) from a Stock Market Crash

    Connect with Benjamin Brandt
    • Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
    • Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter
    • Work with Benjamin: https://retirementstartstoday.com/start

    Get the book - out now!
    Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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    24 mins
  • Sneaky Retirement Taxes (The Tax Traps You Never Saw Coming), Ep #394

    Sneaky Retirement Taxes (The Tax Traps You Never Saw Coming), Ep #394
    Mar 31 2025

    Most people assume their tax burden lightens in retirement, but what if I told you that some taxes are actually designed to creep up on you year after year—without Congress passing a single new law? In this episode, we expose the sneaky taxes that can quietly erode your retirement income, from Social Security taxation to Medicare IRMAA surcharges. These hidden costs don’t just affect the ultra-wealthy anymore; thanks to outdated rules and inflation, they’re hitting everyday retirees harder than ever.

    If you're relying on Social Security, investment income, or Medicare in retirement, you may already be on the IRS’s radar—without realizing it. We break down the four biggest tax traps, explain how they’ve changed over time, and why they’re pulling more retirees into the tax net each year. Whether it's the frozen thresholds for Social Security taxes or the stealthy Medicare penalties that kick in just because you had a good income two years ago, these sneaky policies can add up fast.

    By the end of this episode, you’ll have a clearer picture of how these taxes work, why they exist, and what—if anything—you can do to soften the blow. If avoiding unnecessary taxes in retirement sounds like a smart move, you won’t want to miss this one!

    Outline of This Episode
    • (0:00) Sneaky Retirement Taxes
    • (3:20) Sneaky Tax #1: Social Security taxation (how frozen thresholds trap retirees)
    • (5:10) Sneaky Tax #2: Capital loss deduction limit (unchanged since 1978!)
    • (6:55) Sneaky Tax #3: Medicare IRMAA (tracking your income before you even retire)
    • (08:45) Sneaky Tax #4: Net Investment Income Tax (how it quietly pulls in more taxpayers)
    • (09:40) Wrap-up – Why these taxes persist & what you can do about them
    Resources & People Mentioned
    • The Retirement Podcast Network
    • Social Security Administration’s Taxation of Benefits
    • IRS Q&A on Net Investment Income Tax
    Connect with Benjamin Brandt
    • Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
    • Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter
    • Work with Benjamin: https://retirementstartstoday.com/start

    Get the book - out now!
    Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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    20 mins
  • Five Key Retirement Challenges (and Solutions), Ep #393

    Five Key Retirement Challenges (and Solutions), Ep #393
    Mar 24 2025

    Most people focus on saving for retirement, but what happens when you actually get there? Retirement isn’t just about having enough money—it’s about managing risks that can threaten your financial security and lifestyle.

    In this episode, we explore Five Key Retirement Challenges (and Solutions), inspired by a Kiplinger’s Personal Finance article by Walt West. From unexpected market downturns to rising healthcare costs, these challenges can catch retirees off guard if they’re not prepared.

    We break down each challenge—financial instability, healthcare expenses, taxes, inflation, and estate planning oversights—and discuss practical strategies to navigate them. Learn how to structure a flexible withdrawal plan, prepare for long-term care costs, use tax-efficient strategies like Roth conversions, and ensure your estate plan protects your loved ones.

    Plus, we tackle a listener question about using a MIGA ladder strategy to bridge the gap until Social Security—offering insights into the pros and cons of annuities in a retirement portfolio.

    If you want to retire with confidence and avoid costly missteps, this episode is a must-listen. Whether you're years away from retirement or already in it, understanding these key challenges and their solutions can help you make smarter financial decisions for the road ahead.

    Outline of This Episode
    • (0:00) 5 Key Retirement Challenges (and Solutions)
    • (1:17) Retirement headline: Kiplinger’s article on retirement challenges
    • (1:42) Challenge #1: Financial instability
    • (4:09) Challenge #2: Healthcare and long-term care costs
    • (6:33) Challenge #3: Taxes in retirement
    • (7:33) Challenge #4: Inflation’s impact on retirement income
    • (8:32) Challenge #5: Estate planning oversights
    • (10:25) Listener question: MIGA ladder strategy for retirement income
    Resources & People Mentioned
    • The Retirement Podcast Network
    • Kiplinger’s Personal Finance “Five Key Retirement Challenges” by Walt West
    • Fidelity’s Healthcare in Retirement Report
    Connect with Benjamin Brandt
    • Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
    • Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter
    • Work with Benjamin: https://retirementstartstoday.com/start

    Get the book - out now!
    Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

    Follow Retirement Starts Today in
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    19 mins
  • Top 3 Retirement Mistakes - An Interview with Mr Retirement, Ep #392

    Top 3 Retirement Mistakes - An Interview with Mr Retirement, Ep #392
    Mar 17 2025

    Click here to work with us!

    Most people plan for retirement by focusing on their savings and investment returns—but what if some of the most important decisions happen after you stop working?

    In this episode, I sit down with Jeremy Keil, also known as Mr. Retirement, to discuss the three biggest mistakes retirees make—mistakes that can cost them financial security, tax savings, and peace of mind.

    From misunderstanding the best time to take Social Security to underestimating how long retirement will last, we break down the key oversights that can derail even the best-laid plans.

    Jeremy and I dive into why retirement age and Social Security claiming don’t have to go hand in hand, how to accurately gauge your longevity to avoid outliving your money, and the crucial difference between optimizing for next month’s income versus planning for a lifetime of financial security.

    Whether you’re a few years away from retirement or already in it, this conversation will challenge the way you think about your financial future and equip you with strategies to make smarter decisions.

    Outline of This Episode
    • (0:00) Intro
    • (1:19) Mistake #1 – Tying retirement to Social Security
    • (4:05) Mistake #2 – Underestimating longevity
    • (8:41) Planning for an earlier retirement than expected
    • (13:50) Mistake #3 – Optimizing for short-term income over long-term security
    • (19:20) Where to find more from Mr. Retirement
    Resources & People Mentioned
    • The Retirement Podcast Network
    • Mr. Retirement YouTube Channel
    • Longevity Illustrator Tool
    Connect with Jeremy Keil
    • Connect with Jeremy Keil AKA Mr Retirement on LinkedIn
    Connect with Benjamin Brandt
    • Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
    • Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter
    • Work with Benjamin: https://retirementstartstoday.com/start

    Get the book - out now!
    Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

    Follow Retirement Starts Today in
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    22 mins
  • The 2% Trap: Why Retirees Spend Far Less Than They Could, Ep #391

    The 2% Trap: Why Retirees Spend Far Less Than They Could, Ep #391
    Mar 10 2025
    Click here to work with us! Many retirees enter their golden years with the goal of financial security, but what if the biggest risk isn’t running out of money—it’s not spending enough of it? A surprising new study reveals that retirees are withdrawing just 2% a year from their savings—barely half of what’s traditionally considered safe. This cautious approach might seem responsible, but it often leads to unnecessary frugality, missed experiences, and larger-than-expected tax burdens later in life. The hesitation to tap into personal savings, even when there's plenty available, raises an important question: What’s stopping retirees from spending with confidence? Research shows that retirees feel much more comfortable spending guaranteed income from sources like Social Security and pensions while being reluctant to withdraw from their own investments. This behavioral tendency can leave money unspent for decades, only to be forced out later through required minimum distributions (RMDs) that create tax inefficiencies. Meanwhile, large inheritances often arrive too late to make a meaningful impact on the next generation. Rethinking the 2% mindset means understanding what keeps retirees locked into ultra-conservative spending habits and finding ways to turn savings into income that feels reliable. A simple shift—such as automating monthly withdrawals or adjusting expectations around financial security—can open the door to a more fulfilling retirement. The money was saved to be spent, and spending it well can be just as important as saving it wisely. Spending too little can be just as costly as spending too much. With the right approach, retirees can enjoy their wealth now while keeping future financial security intact. Outline of This Episode (0:00) Why Retirees Spend Far Less Than They Could(1:46) The study: Retirees underspending their savings(3:33) Why the 2% problem exists(6:10) The impact of underspending on taxes & an inheritance(8:11) The role of financial planning & behavioral coaching(9:20) Possible solutions: Turning savings into reliable income(11:04) Listener question: A simple withdrawal plan Resources & People Mentioned The Retirement Podcast NetworkDavid Blanchett – Head of Retirement Research at PGIM DC SolutionsMichael Finke – The American College of Financial ServicesDie With Zero by Bill Perkins – Book on intentional retirement spending Connect with Benjamin Brandt Get the Retire-Ready Toolkit: http://retirementstartstodayradio.comSubscribe to the newsletter: https://retirementstartstodayradio.com/newsletterWork with Benjamin: https://retirementstartstoday.com/start Get the book - out now!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement Follow Retirement Starts Today inApple Podcasts, Spotify, Overcast, Pocket Casts, Amazon Music, or iHeart
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    16 mins
  • From Saver to Spender: How to Confidently Use Your Nest Egg, Ep 390

    From Saver to Spender: How to Confidently Use Your Nest Egg, Ep 390
    Mar 3 2025
    Click here to work with us! For decades, you've been focused on saving—watching your retirement accounts grow, sticking to a budget, and making smart financial decisions to ensure a secure future. But now that the time has come to actually enjoy your hard-earned money, spending it feels... unsettling. You’re not alone. Many retirees struggle with the mental shift from accumulation to decumulation, even when their financial plans show they have more than enough. The fear of running out, coupled with conflicting financial advice, makes it tough to confidently transition into this new phase of life. Today we explore strategies for overcoming the retirement spending fear, based on an insightful Forbes article by Tim Maurer. We’ll break down his three-step approach: phasing into retirement instead of stopping abruptly, redefining "work" to maintain purpose and fulfillment, and structuring an investment portfolio designed specifically for retirement withdrawals. Plus, we’ll tackle a listener question about Social Security spousal benefits and the implications of early filing. By the end of the episode, you'll gain a clearer understanding of how to embrace your retirement, spend with confidence, and fully enjoy the wealth you’ve built. Outline of This Episode (0:00) The fear of spending in retirement(1:19) The “Retirement Cycle of Fear”(3:13) Step 1: Phase into retirement gradually(5:15) Step 2: Keep working, but redefine it(7:20) Step 3: Build a portfolio for spending(10:14) Listener Q – Social Security & spouses(14:30) Final thoughts (how to thrive in retirement) Resources & People Mentioned The Retirement Podcast NetworkTim Maurer’s Forbes article – Overcoming the fear of spending in retirement.Daniel Crosby’s The Soul of Wealth – A deep dive into money and psychology. Connect with Benjamin Brandt Become a Client: www.retirementstartstoday.com/startGet the Retire-Ready Toolkit: http://retirementstartstodayradio.com/Follow Ben on Twitter: https://twitter.com/retiremeasapJoin the newsletter: https://retirementstartstodayradio.com/newsletterDive deeper into retirement planning with Ben at www.RetirementIncome.University Subscribe to Retirement Starts Today on Apple Podcasts, Stitcher, TuneIn, Podbean, Player FM, iHeart, or Spotify
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    17 mins
  • 7 Inefficiencies on Rich Retirees' Tax Returns, Ep #389

    7 Inefficiencies on Rich Retirees' Tax Returns, Ep #389
    Feb 24 2025
    Click here to work with us! A lot of retirees assume their tax situation gets simpler once they stop working, but that’s not always the case. There are plenty of ways high-net-worth retirees end up paying more than they need to—sometimes without even realizing it. Maybe it’s interest and dividend income getting taxed at higher rates, or IRA withdrawals happening earlier than necessary. Maybe it’s something as simple as missing the right way to report charitable giving. These things add up, and over time, they can quietly eat away at retirement savings. Some of the biggest inefficiencies show up on tax returns in ways people don’t always expect. Social Security benefits taken too soon, mutual funds kicking off surprise capital gains, or estimated tax payments falling short and triggering penalties—it all matters. There are ways to structure income, investments, and withdrawals to keep more of what’s earned, but they take a little planning. The goal isn’t just to minimize taxes for the sake of it, but to make sure every dollar is working as efficiently as possible. Most of these inefficiencies can be fixed with a few small adjustments. Some require a different way of thinking about income in retirement, others just mean taking advantage of tax rules that are already there. Either way, it’s worth a closer look. A little awareness now can mean thousands saved over the years. Outline of This Episode (0:00) Inefficiencies on Rich Retirees' Tax Returns(4:07) Top tax inefficiencies: Interest, dividends, and premature IRA withdrawals(6:52) Charitable distributions, Social Security timing, and phantom capital gains(9:33) Capital gains, charitable intent, and avoiding underpayment penalties(12:24) Listener question: Travel spending habits of wealthy retirees(19:05) Listener question: Callable CDs and interest rate risk(21:16) Closing thoughts and practical takeaways Resources & People Mentioned The Retirement Podcast NetworkKiplinger’s ArticleTurboTax Safe Harbor GuideFidelity Charitable Connect with Benjamin Brandt Become a Client: www.retirementstartstoday.com/startGet the Retire-Ready Toolkit: http://retirementstartstodayradio.com/Follow Ben on Twitter: https://twitter.com/retiremeasapJoin the newsletter: https://retirementstartstodayradio.com/newsletterDive deeper into retirement planning with Ben at www.RetirementIncome.University Subscribe to Retirement Starts Today on Apple Podcasts, Stitcher, TuneIn, Podbean, Player FM, iHeart, or Spotify
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    22 mins
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