Episódios
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What do you do with RMDs you don’t actually need?
If you’re retired and over age 73 — or 75 if you were born in 1960 or later — you know the IRS requires you to start taking Required Minimum Distributions (RMDs) from your traditional IRAs and workplace retirement accounts.
Even if you don’t need that money for living expenses, you still have to take it - which means more taxable income, higher Medicare premiums, and a bigger chunk of your Social Security benefits becoming taxable in some cases.
Today I share "6 Strategic Ways to Make the Most of Distributions You Don’t Need", an article by Greg Hammons from TheStreet.com.
Reinvest in a Taxable Brokerage Account - super straightforward. Make a Qualified Charitable Distribution (QCD) Use RMDs to Fund Life Insurance Cover the Taxes on a Roth Conversion Fund a 529 Plan for Education Give to Family—Tax-FreeSo what’s the best move for you?
That depends on your goals—whether it’s growing your money, reducing taxes, helping your family, or supporting a cause. But the key message is this: RMDs don’t have to be a tax burden. With some intentional planning, they can be an opportunity.
Before making a move, talk to your financial planner or tax pro. These strategies can have long-term effects on your retirement plan, your taxes, and your legacy.
I also tackle a listener question: "What is your recommendation to cover the gap in sustainable income from pre-retirement (e.g., 60) to Social Security claiming age (e.g., 70)?"
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/startGet the book!
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What happens when your emergency cash runs dry—and life keeps happening?
A recent article lays out a ranked list of ten ways to access emergency cash, starting with the best options and ending with the ones you’ll want to avoid unless it’s truly a last resort:
Emergency Fund / Short-Term Securities Low-Risk Assets in Taxable Accounts Roth IRA Contributions Life Insurance Cash Values 401(k) Loan Home Equity Line of Credit (HELOC) Hardship Withdrawals from 401(k) Reverse Mortgage Margin Loans Credit CardsThe takeaway?
Know your emergency funding hierarchy before a crisis hits. With a plan in place, you’ll be better equipped to make calm, informed decisions when life throws you a curveball.
Resource:
MorningStar article by Christine Benz: 10 Sources of Emergency Cash, Ranked From Best to Worst Christine Benz’s book - How to Retire: 20 Lessons for a Happy, Successful, and Wealthy Retirement https://a.co/d/3rZ3JgF 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/startGet the book!
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“By the time your child turns 18, you’ve spent 95% of the time you’ll ever spend with them in your lifetime.”
This comes from research by the American Time Use Survey, highlighted by Our World in Data. And let’s be honest, when you first hear that, it stings a little. Especially as a parent. You can’t help but wonder, “Have I been a good steward of that precious time?”
But here’s the twist: this isn’t about guilt. It’s about awareness. It’s a gentle, data-backed nudge to savor the moments that feel small now—but that become the biggest memories later.
So how do we maximize the return on the time—and the money—we spend on experiences? Research tells us something powerful: experiences give us more lasting happiness than stuff. That’s not just my opinion, that’s from a 2020 study by Kumar, Killingsworth, and Gilovich. Experiences beat material goods both in prospect and in retrospect. In other words, we enjoy them more before and after they happen.
Step 1: Listen & Learn
Step 2: Create Curiosity
Step 3: Build Together
Step 4: Build Up—and Look BackWhat does this have to do with retirement? EVERYTHING!
Listen in to understand why.
I also answer a question from Wendell, a retiree who’s considering swapping out some of his stock-heavy portfolio for the safety of short-term government bonds — a strategy known as “T-Bills and Chill.” He’s wondering: with guaranteed income already in place, is it time to say goodbye to the stock market for good?
Resource:
Forbes article by Tim Maurer: A Method For Maximizing Memories With Money
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/startGet the book!
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We’re talking about rebalancing! Rebalancing is key to any retirement plan, but how often should we do it? That’s the topic of today’s retirement headlines segment, where we’re going to look at an article by by Jennifer Reed
Key discussion points:
💵 Financial Considerations
💔 Emotional Considerations
🧩 Relational Considerations
📊 A Look at the NumbersResource:
Article by Jennifer Reed: Is The Optimal Rebalancing Strategy To Not Rebalance At All? https://www.fa-mag.com/news/is-there-an-optimal-rebalancing-strategy--maybe-82136.htmlAfter that, I answer a listener question: “Could you discuss the financial emotional and relationship issues with disclaiming an inheritance?”
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/startGet the book!
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What are the perceived benefits of moving to a low-tax state in retirement? Is it all it’s cracked up to be?
We’re gonna cover a Wall Street Journal article by Debbie Carlson that delivers an important dose of nuance: “Don’t let the income-tax tail wag the total-spending dog.”
I also answer a very thoughtful question from Lynn about sequence of returns risk, as well as average returns vs order of returns.
Key topics from the article:
🏠 Real Estate & Insurance Can Eat Up the Savings
📊 For Middle-Income Retirees, Sales & Property Taxes Matter More
💵 Homeowners Insurance Is a Big—and Growing—Expense
📚 Don’t Forget State-Level Retirement & Estate Taxes
🧮 Ben’s Take: Look at the Whole Picture
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
Resource:
Article by Debbie Carlson: https://www.wsj.com/personal-finance/taxes/retirement-low-tax-rate-states-move-cabdb31bGet the book!
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How do you stay calm and confident when the markets get messy? In today's Retirement Headlines we go through Cullen Roche's article from Discipline Funds - "Finding Certainty in a Sea of Uncertainty".
With tariffs, global uncertainty, and market volatility making headlines again offers nine practical steps to help you stay grounded, focused, and on track with your retirement plan.
The 9 Calming, Confidence-boosting steps the article lays out are:
Revisit Your Financial Plan Update Your Estate Plan Consider Tax Loss Harvesting Dollar Cost Average Excess Cash Think in Terms of Time Horizons Stay the Course (If You Can) Talk About It Focus on What You Can Control Go Do "Leg Day"After that, I answer a listener question: “I’ve been paying $1,600 a year for a $500,000 level term life insurance policy, which runs through 2031. I have two financially stable adult children in their 30s, who are the policy’s beneficiaries, and two grandchildren. Should I keep making the premium payments—or let it lapse?”
Resource:
Article by Cullen Roche: Finding Certainty in a Sea of Uncertainty
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!
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One of the biggest and often overlooked risks facing retirees is sequence-of-returns risk. The risk of experiencing investment losses early in retirement can have an impact on the sustainability of savings over the long term.
Morningstar researchers dug into this in their latest State of Retirement Income study. Their findings confirm what many retirement planners already suspect: the first five years of retirement are make-or-break.
I'll also answer a listener question: "Are there advantages to moving all your mutual funds into a brokerage firm such as Schwab? "
Resource:
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
Morningstar article: How to Avoid Outliving Your Retirement Savings? It’s All in the SequenceGet the book - out now!
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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 StrategyThen 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/startGet the book - out now!
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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 SellResources:
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/startGet the book - out now!
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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/startGet the book - out now!
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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/startGet the book - out now!
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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/startGet the book - out now!
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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 Network David Blanchett – Head of Retirement Research at PGIM DC Solutions Michael Finke – The American College of Financial Services Die With Zero by Bill Perkins – Book on intentional retirement spending 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/startGet the book - out now!
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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 Network Tim 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/start Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/ Follow Ben on Twitter: https://twitter.com/retiremeasap Join the newsletter: https://retirementstartstodayradio.com/newsletter Dive deeper into retirement planning with Ben at www.RetirementIncome.UniversitySubscribe to Retirement Starts Today on
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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 Network Kiplinger’s Article TurboTax Safe Harbor Guide Fidelity Charitable Connect with Benjamin Brandt Become a Client: www.retirementstartstoday.com/start Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/ Follow Ben on Twitter: https://twitter.com/retiremeasap Join the newsletter: https://retirementstartstodayradio.com/newsletter Dive deeper into retirement planning with Ben at www.RetirementIncome.UniversitySubscribe to Retirement Starts Today on
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Most people plan for retirement by focusing on their finances—building up a nest egg, securing passive income, and minimizing taxes. But what if that’s only part of the equation? Many retirees find themselves financially secure yet feeling unexpectedly lost, disengaged, or even unhappy. The truth is, money alone doesn’t guarantee a fulfilling retirement.
Dr. Daniel Crosby explains how work naturally provides purpose, engagement, relationships, and growth—key elements we often lose in retirement without realizing it. Without a plan to replace them, retirees risk dissatisfaction, depression, and even health issues.
The good news? By proactively designing your retirement around these five pillars—positive experiences, engagement, relationships, meaning, and growth—you can create a life that is just as rich in purpose as it is in financial security.
Whether it’s through hobbies, social groups, volunteering, or personal growth, Dr. Crosby shares how to build a retirement that keeps you mentally, emotionally, and socially fulfilled for decades to come.
Outline of This Episode (0:00) Introduction (1:30) The unexpected struggles of retirement (2:40) The five facets of a meaningful life (6:23) How to intentionally rebuild purpose after retiring (9:50) The hidden danger of loneliness in retirement (14:30) Why purpose-driven money decisions matter (22:50) A hilarious twist: How Elon Musk “stole” from Dr. Crosby! Resources & People Mentioned The Retirement Podcast Network Dr. Daniel Crosby’s Book – The Soul of Wealth (Amazon) Dr. Daniel Crosby’s Podcast – Standard Deviations (Podcast) CDC Report on Loneliness & Health Risks (Report) Connect with Dr. Daniel Crosby Chief Behavioral Officer bio His Twitter/X: @danielcrosby His LinkedIn: Dr. Daniel Crosby Connect with Benjamin Brandt Become a Client: www.retirementstartstoday.com/start Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/ Follow Ben on Twitter: https://twitter.com/retiremeasap Join the newsletter: https://retirementstartstodayradio.com/newsletter Dive deeper into retirement planning with Ben at www.RetirementIncome.UniversitySubscribe to Retirement Starts Today on
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Many people fear running out of money in retirement, assuming they'll struggle financially once they stop working. But a recent Gallup poll shows 80% of retirees have enough to live comfortably, despite concerns about Social Security, longevity risk, and pension declines.
Why the difference between expectation and reality? Many retirees find their expenses drop, Medicare covers more than expected, and Social Security plays a bigger role in their income.
However, many still claim Social Security early, leaving money on the table. By making strategic choices, like delaying Social Security and managing retirement savings wisely, you can secure a more stable, stress-free future.
If you're anxious about your retirement income, you're not alone—but retirees before you have found their finances more stable than they expected. By taking the right steps now, you can be part of that 80% who enjoy a confident retirement.
Outline of This Episode (0:00) Concerns vs. Reality (1:30) The Gallup poll and retirement reality (5:00) The Social Security dilemma and when to claim (9:10) The shift from pensions to 401(k)s (11:17) Listener question: Pros and cons of 55+ communities (18:30) Why renting before buying can save you money (21:00) Final takeaways and episode wrap-up Resources & People Mentioned The Retirement Podcast Network Gallup poll on retirement confidence 55+ community comparison site Emile Hallez’ Investment News retirement article Connect with Benjamin Brandt Become a Client: www.retirementstartstoday.com/start Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/ Follow Ben on Twitter: https://twitter.com/retiremeasap Join the newsletter: https://retirementstartstodayradio.com/newsletter Dive deeper into retirement planning with Ben at www.RetirementIncome.UniversitySubscribe to Retirement Starts Today on
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Listen in to this BONUS episode as Canadian CFP and host of the Your Retirement Planning Simplified Podcast, Joe Curry, interviews me (Benjamin) about:
The non-financial aspects of retirement planning Shifting from a scarcity to an abundance mindset Retiring to something rather than from something and embracing creativity to design a fulfilling post-career lifeKey insights include overcoming spending anxiety, identifying passions, building social connections, and planning purposefully for a no-regrets retirement. With actionable insights and a focus on mindset, this episode is perfect for those looking to simplify and enrich their retirement journey.
Enjoy!
Resources:
Joe Curry's website and podcast
Joe Curry on LinkedIn
Book: Be Your Future Self Now by Dr. Benjamin Hardy
Inspiration for understanding and connecting with your future self to create a fulfilling retirement. Connect with Benjamin Brandt Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com Follow Ben on Twitter: https://twitter.com/retiremeasap Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletterGet the book - out now!
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Employee benefits are one of the most overlooked aspects of financial planning. We often check a few boxes during open enrollment and move on—but are we truly maximizing what’s available to us?
This week, we sit down with Joe Saul-Sehy, host of Stacking Benjamins, to uncover the hidden value in workplace benefits. From disability insurance pitfalls to term vs. whole life insurance, Joe walks us through key strategies to ensure we’re not leaving money (or protection) on the table.
Joe also introduces a powerful HR benefits guide, a resource designed to help us navigate workplace perks with confidence. Whether it's understanding own-occupation disability insurance, avoiding junk policies, or knowing when to self-insure, this conversation is packed with actionable advice. If you’ve ever wondered whether you’re making the most of your benefits—or if you’re just blindly accepting what’s offered—this episode is for you.
Outline of This Episode (0:00) Maximizing Workplace Benefits (2:32) Disability Insurance: Are You Really Covered? (6:50) The Truth About Accidental Death Policies (10:30) How Your Emergency Fund Can Replace Certain Insurances (14:50) The Hidden Costs of Small-Dollar Insurance Policies (18:00) Term vs. Permanent Life Insurance: What’s Right for You? (24:20) How Much Life Insurance Do You Actually Need? (27:40) The Ongoing Evolution of Workplace Benefits & Joe’s HR Guide Resources & People Mentioned The Retirement Podcast Network Website: Stacking Benjamins Connect with Joe Saul-Sehy Twitter: @AverageJoeMoney Instagram: @StackingBenjamins LinkedIn: Joe Saul-Sehy Connect with Benjamin Brandt Become a Client: www.retirementstartstoday.com/start Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/ Follow Ben on Twitter: https://twitter.com/retiremeasap Join the newsletter: https://retirementstartstodayradio.com/newsletter Dive deeper into retirement planning with Ben at www.RetirementIncome.UniversitySubscribe to Retirement Starts Today on
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What if you could turn those green numbers in your investment account into retirement income while paying as little in taxes as possible? That’s exactly what we’re covering today with Peter Lazaroff, Chief Investment Officer at PlanCorp. We’re tackling the challenge many of us face: managing deferred gains in our portfolios and figuring out the smartest ways to reduce the tax hit as we transition to retirement.
Peter and I talk through a range of strategies for handling concentrated stock positions, whether it’s selling off winners gradually, taking advantage of tax-loss harvesting, or exploring more advanced options like exchange funds or a 351 exchange. These aren’t just dry financial concepts—they’re real, actionable ideas that can help you simplify your portfolio and make the most of what you’ve saved. And trust me, simplifying your financial “closet” can feel like a huge weight lifted.
We also talk about the emotional side of investing. Why does it feel so hard to part with stocks that have been good to us? Whether it’s an attachment to the company or pride in your early picks, Peter shares why these feelings matter and how to move past them to make decisions that better serve your long-term goals. Stick around—you won’t want to miss the insights he has to share.
Outline of This Episode (0:20) Peter Lazaroff’s Options for Reducing Taxes on Deferred Gains Pre-Retirement (01:46) Why retirees need to manage large brokerage gains. (03:10) The emotional challenge of selling winning stocks. (05:20) Risks of concentrated stock positions and diversification. (09:00) Tax-loss harvesting and direct indexing strategies. (14:30) Simplifying portfolios with the 351 exchange. (18:40) Portfolio simplicity and enjoying retirement income. Resources & People Mentioned The Retirement Podcast Network Peter Lazaroff’s Book: "Making Money Simple" – www.peterlazaroff.com/freebook Peter Lazaroff’s Website – peterlazaroff.com The Long Term Investor Podcast – thelongterminvestor.com Connect with Peter Lazaroff Peter's website Connect with Benjamin Brandt Become a Client: www.retirementstartstoday.com/start Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/ Follow Ben on Twitter: https://twitter.com/retiremeasap Join the newsletter: https://retirementstartstodayradio.com/newsletter Dive deeper into retirement planning with Ben at www.RetirementIncome.UniversitySubscribe to Retirement Starts Today on
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