Explorez tous les épisodes du podcast Stay Wealthy Retirement Podcast
| Titre | Date | Durée | |
|---|---|---|---|
| 8 Stealth Taxes That Can Leave the IRS a Tip (And How to Avoid It) | 29 oct. 2026 | 00:22:55 | |
Most retirees have a general idea of which tax bracket they're in. But that bracket doesn't always tell you what your next dollar of income really costs. Cross certain income thresholds, and you could face an extra surtax, lose part of a deduction, or pay higher Medicare premiums. These are often called stealth taxes. And as year-end approaches, they can quickly change the math on a Roth conversion, a capital gain, or an extra IRA withdrawal. In this episode, I'm breaking down 8 stealth taxes that are easy for retirement savers to overlook. Here's what you'll learn: → Why some of the best years for Roth conversions can also create the most expensive planning trade-offs → Why some income thresholds deserve careful attention while others may be worth crossing intentionally → A simple 3-scenario exercise to run before you lock in your year-end decisions Avoiding every one of these taxes isn't always the goal. Sometimes paying more today can help you keep more of your wealth over the next 10, 20, or even 30+ years. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| The $450,000 Celebrity Scam (Plus Your Passkey Questions, Answered) | 22 oct. 2026 | 00:31:40 | |
On Christmas Day, a woman picked up her 74-year-old mother's phone and found messages from someone she didn't recognize. What she uncovered had been unfolding for nearly a year, cost her mom hundreds of thousands of dollars, and started with something millions of people do every day. And to her mom, none of it felt suspicious. That's what can make scams like this so difficult to recognize, even for careful, intelligent people. But other financial threats don't require criminals to earn your trust at all. In this episode, I'm sharing what her story can teach us about protecting our money. I'm also sharing what you need to know about passkeys, a newer (and safer!) way to sign in to your online accounts. Here's what you'll learn: → 4 simple habits that can make it harder for scammers to earn your trust → How passkeys work, the 3 places to store them, and what happens if you lose your phone → How criminals can sometimes access your accounts without needing your password, passkey, or verification code The best protection is layered: stronger security on your accounts, a few simple habits, and someone you trust to call before you act. *** 📥 Grab Your Free Retirement Security Checklist: This 9-page guide helps you close the most common security gaps in about an hour. Inside, you'll find family scam-prevention rules, passkey and credit freeze guides, and a plan for what to do if something goes wrong. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| Why the S&P 500 Isn't Enough Once You Retire (And 5 Tax-Smart Steps to Diversify) | 15 oct. 2026 | 00:25:19 | |
Warren Buffett has shared exactly how the money his family inherits should be invested: 90% in a low-cost S&P 500 index fund and 10% in short-term government bonds. It's simple, inexpensive, and recommended by the greatest investor of all time. And if you've owned the S&P 500, your company's stock, or a single big winner for decades, it may be a big reason you're able to retire. But once your portfolio has to provide a paycheck, that concentration can carry risks it didn't before. In this episode, I'm sharing how to decide whether what got you here still fits the retirement ahead. Here's what you'll learn: → Why the same portfolio can look very different once you start taking withdrawals → What you may give up by spreading your money around (and why it can still make sense) → A simple 5-step process for reducing a concentrated position while keeping taxes in check If you were building your portfolio today, knowing what you need your money to do, would you choose the same mix? *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| Is Social Security Going Broke? (And 6 Other Myths Worth Unlearning) | 08 oct. 2026 | 00:26:22 | |
Last week, I explained why waiting until 70 to claim Social Security deserves a closer look, even when it makes sense on paper. Weighing that decision depends on understanding how the program works. And a few common assumptions can make that harder than it needs to be. They can influence when you retire, how you plan for taxes, and what your spouse may receive down the road. In this episode, I'm walking through 7 common Social Security myths and where the confusion comes from. Here's what you'll learn: → What the trust fund's projected shortfall may (and may not) mean for your benefits → How your benefit is calculated, and why high earners often misjudge it → 3 options that may still be available if you've already claimed early Whether you're years away from claiming or already collecting, a clearer picture of the rules can make it easier to choose an approach that fits the rest of your retirement plan. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| The Case for Claiming Social Security Early (Even If You Can Afford to Wait) | 01 oct. 2026 | 00:16:33 | |
If you've researched when to claim Social Security, you've probably heard to wait until age 70. And there's good reason for that advice. Waiting means a larger monthly benefit for life, which can be especially valuable if your retirement lasts several decades. But while you wait, you'll need to cover your expenses from other sources. That means considering how comfortable you are drawing from savings, how a market downturn could affect your plan, and how many healthy, active years you have ahead. So, how do you weigh those trade-offs? And when might claiming earlier make sense, even if you can afford to wait? In today's episode, I'm exploring 6 overlooked considerations that could influence your claiming strategy and help you decide whether the advice to wait fits your retirement plan. We'll look at how they might influence your claiming strategy, and why a recommendation that sounds sensible on paper may need a closer look in your own retirement plan. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| Why Your Charitable Deduction Can Disappear (Even With a Receipt) | 24 sept. 2026 | 00:23:25 | |
📥 Grab Your Free Charitable Giving Planning Resources: Charitable giving can be simple, but the tax and planning decisions behind it often are not. Get four practical resources to help you make more informed giving decisions: A QCD guide, a donor-advised fund guide, a breakdown of which assets may be best to give, and an overview of the charitable-giving vehicles available when your planning gets more complex. → Download All 4 Resources Here *** 🎙️ Episode Description: Earlier this year, the U.S. Tax Court threw out a $665,000 charitable deduction. The donors had an appraisal, the required IRS form, and a signed letter documenting the donation. And yet the court denied the entire deduction... because of ONE missing sentence. And that same requirement can apply when you write a check to your church, give from your IRA, or buy tickets to a charity gala. In this episode, I walk through what went wrong and what it can teach the rest of us. Here's what you'll learn: → Why a canceled check alone may not be enough to back up your deduction → How QCDs, appreciated stock, and new 2026 rules can change the tax outcome of the same donation → The 4 questions I'd ask before making your next charitable gift The charity gets your gift either way. The question is whether you get the tax benefit, too. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| 3 Things RMD Timing Actually Affects (And How to Choose Your Schedule) | 17 sept. 2026 | 00:15:09 | |
Once required minimum distributions begin, the IRS decides how much comes out of your IRA each year. But it doesn't decide when... You can take it all in January, wait until December, or spread it out across the year. At first glance, the choice seems almost meaningless. The required amount is the same, and the distribution still lands in the same tax year. But the timing can matter in ways that aren't always obvious. And even if you're years away from taking RMDs, this is a decision you'll eventually need to make if you have money in pre-tax retirement accounts. Here's what you'll learn: → The 3 things RMD timing can still affect (and how much each one really matters) → Why the order of your RMD, charitable gifts, and Roth conversions can matter more than the month you withdraw → When taking your RMD early, late, or throughout the year makes the most sense By the end, you'll have a simple framework for thinking about RMD timing before it becomes another retirement decision you're forced to make on the fly. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| Are You Really Behind on Retirement? 2 Studies Disagree (46% vs. Under 20%) | 10 sept. 2026 | 00:19:35 | |
One multi-decade study suggests nearly half of working households may be at risk of falling short in retirement. But another respected study found that fewer than 20% were actually behind. So which one should you believe? The answer reveals a weakness in the way we typically measure retirement progress. Here's what you'll learn: → Why 2 respected studies reach such different conclusions about who's really at risk → The 3 ways the "save a percentage" rule can break down for families → Why the years when saving feels impossible may be more normal than you've been told → How your 50s and 60s can become the most important saving windows of your life. By the end, you'll have a better way to judge whether you're truly behind and a clearer picture of the opportunities that may still be ahead. And if nothing else, you'll understand why a difficult savings season today doesn't necessarily define where you'll end up. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| Your Plan Says Spend — Your Gut Says No (5 Questions to Ask Instead) | 03 sept. 2026 | 00:18:25 | |
Most retirement planning treats the transition like a single event. But in reality, you're navigating THREE different shifts at the same time. And while traditional planning is well-equipped to handle the first, it spends far less time on the second and almost none on the third. Here's what you'll learn: → Why 50% of retirees plan to spend little or none of their savings → Why even a well-funded retiree can treat every withdrawal like a threat → 5 questions that work better than "Can I afford it?" By the end, you'll have a clearer picture of which transition your plan may be overlooking, why that matters, and what it can take to close the gap. And if nothing else, you'll have a better answer for why spending your own money can feel so difficult after decades of doing everything right. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| 8 Investing Numbers That Shape Whether Your Nest Egg Outlives You | 27 août 2026 | 00:22:19 | |
You've spent decades building a nest egg large enough to fund the retirement you want. The next challenge is making sure it can support that same lifestyle for the next 30 years. At 3% historical inflation, the $100,000 lifestyle you retire on could cost $240,000 a year by age 90. And the assets that feel safest — cash, CDs, and money market funds — have historically done the least to keep up. In this episode, I'm simplifying a century of market history into 8 numbers that shape how long your money lasts. Here's what you'll learn: → The hidden cost of playing it safe with money you won't need for decades → The 2 bond numbers that look nearly identical, and the risk hiding between them → How they all fit together into a simple framework for making confident decisions My hope is that when we're done, you have a small set of reference points to return to, and a lot less noise competing for your attention. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| The 4 Retirement Income Styles (And How to Find Yours) | 20 août 2026 | 00:18:24 | |
Two retirees can have the same age, the same nest egg, and the same monthly expenses. Give them the exact same retirement income plan, and one may feel completely comfortable while the other loses sleep the moment markets fall. That's because retirement income planning involves more than math. It also depends on how much certainty you want, how much flexibility you're willing to give up, and which risks you're comfortable carrying yourself. In this episode, I'm breaking down a practical framework that organizes nearly every retirement income strategy into four distinct styles. Here's what you'll learn: → The 2 questions that shape nearly every retirement income decision → The strengths and tradeoffs behind the 4 most common retirement income strategies → A simple 3-step process for building a plan around your own priorities There may not be one "best" retirement income strategy for everyone. But understanding the tradeoffs can help you build a plan you have the confidence to follow through market declines, changing spending needs, and decades of retirement. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| Do You Really Need $1.5 Million to Retire? | 13 août 2026 | 00:15:05 | |
Americans now say they need $1.5 million to retire comfortably, according to a recent survey. That's nearly 60% higher than the "magic number" reported roughly five years ago, which helps explain why so many retirement savers feel behind. But that number is a survey average, and measuring yourself against it could cost you years you can't get back. In this episode, I'm sharing why retiring at 62 may be more realistic than you think. Here's what you'll learn: → The new Vanguard research that challenges the conventional Social Security advice → How one couple with $1.8 million stopped chasing the $2.5 million their calculator demanded → A simple 4-step process for building (and stress-testing) a flexible early retirement plan For smart, diligent savers, the biggest retirement risk isn't always running out of money... sometimes it's running out of time. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| 3 Spending Surprises From J.P. Morgan's Study of 5 Million Retirees | 06 août 2026 | 00:20:18 | |
Last week, I made the case that many retirees can safely spend more than their plans suggest. Today, the largest bank in the country puts that idea to the test. But instead of relying on surveys, JP Morgan studied real bank transactions from over 5 million American households. The data reveals three spending patterns most retirement plans ignore. And together, they can decide whether a nest egg lasts a full 30-year retirement... or runs out years early. In this episode, you'll learn: → What millions of real bank transactions reveal about retirement spending → The spending surge most people fail to plan for → Why so few retirees rarely spend the way traditional plans assume — and a simple way to protect against it A strong retirement plan isn't built on how retirees say they behave... it's built on how they actually do. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| NEW RESEARCH: Your Plan Is Overestimating Retirement Costs (by 20%) | 30 juil. 2026 | 00:24:14 | |
Most retirement plans assume your spending will rise with inflation every year for the rest of your life. But a new study tracking thousands of American retirees found almost the exact opposite: As many as 85% of households spent less, after adjusting for inflation, than they had 10 years earlier. Even more surprising? That includes retirees who could comfortably afford to maintain their lifestyle! In this episode, I'm breaking down what this new research means for your retirement plan. You'll learn: → Why retirement spending declines even as healthcare costs keep climbing → What the "retirement spending smile" and "smirk" reveal about spending later in life → Why even wealthy retirees continue cutting back as they age → How modeling spending the way retirees actually behave can meaningfully change your safe withdrawal rate If your plan is overestimating the cost of retirement, it's likely underestimating the life you can afford... especially in the early years, when the money delivers the most joy. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call Here *** Episode Resources: | |||
| 5 Steps to Protect Your Aging Parents' Money (Before It's Too Late) | 23 juil. 2026 | 00:27:07 | |
📥 Grab Your Free Estate Planning Resources: Helping an aging parent with their money is a responsibility few families are prepared for. Get three practical resources to help your family take action: A one-page cheat sheet of today's episode, a detailed estate-planning review checklist, and a simple guide to the key documents every family should review. → Download All 3 Resources Here *** 🎙️ Episode Description: Helping an aging parent with their money sounds simple: You step in, pay the bills, and make sure everything is handled. Unfortunately, love and trust don't give you legal authority. And without the right document in place, a bank may refuse to speak with you... even if your parent is sick, bills are going unpaid, or money is needed for their care. That's where a Durable Power of Attorney (DPOA) comes in. But simply having the document isn't enough. The fine print, the powers it grants, and the way you handle the responsibility can make all the difference. In this episode, I explain how a DPOA for finances works and steps you can take to prepare before it's too late. Here's what you'll learn: → The fine-print provision every family should double-check → 5 practical steps for managing an aging parent's finances responsibly → What can happen when the document isn't signed before a parent loses capacity → 4 common mistakes that can create legal, financial, and family problems By the end, you'll know how to prepare for managing your parents' money — and help ensure the person they trust can legally step in when the time comes. *** 📆 Book a Call With Our Team: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. Learn More and Book a Call Here *** Episode Resources: | |||
| Can $5M in T-Bills Safely Fund Your Retirement? (History Says No) | 16 juil. 2026 | 00:15:59 | |
Kevin O'Leary says you only need one thing to retire safely: $5 million in Treasury bills. Not stocks. Not real estate. Just T-bills — and you've "safeguarded your family for life." It sounds like the ultimate safe retirement plan. But when a recent research article tested this advice against 40 years of market history, the results told a very different story. In this episode, I break down the research behind the "T-Bill and Chill" strategy and what it really means for your retirement plan. Here's what you'll learn: → The two hidden forces working against a portfolio built entirely on "safe" assets → What happened to a hypothetical retiree who followed this exact advice → Why Kevin O'Leary might still be right... just not for the reason he thinks By the end, you'll know exactly what job "safe" money should (and shouldn't) have in your retirement plan. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| Why Great Savers Struggle to Spend (5 Steps to Fix It) | 09 juil. 2026 | 00:34:52 | |
Research shows that retirees following traditional withdrawal rules rarely come close to depleting their portfolios. In fact, many end up leaving behind balances that are surprisingly large. Which raises an important question: why is it so hard to spend the money you spent decades saving? Today, I'm revisiting my conversation with Brian Portnoy, Ph.D., CFA to explore the psychology behind the fear of spending and what retirees can do to move through it. Longtime listeners will also recognize Brian as the source of a quote I've shared many times on the show, and in this episode, he finally shares the story behind it. In this episode, we discuss: → Why retirees with healthy, well-funded plans still struggle to spend → The flawed logic behind "If I just had $X, I'd finally feel comfortable" → 5 steps to overcome the fear of spending, whether retirement is five years away or already here → What "funded contentment" means, and why it may be the real difference between being rich and being wealthy Because the goal of retirement planning isn't to die with the biggest possible balance... it's to use your money to support a life that feels meaningful to you. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| 6 (Counterintuitive) Facts About Retirement, Investing, and Longevity | 02 juil. 2026 | 00:20:37 | |
Today, we're stepping away from the spreadsheets, tax strategies, and retirement tactics to have a little fun. I'm sharing six facts that challenge conventional wisdom — including one involving a famous gangster and a reminder that taxes touch almost everything. A few highlights: → The surprising fate of investors who bought the exact top of the dot-com bubble → How much a crystal ball that picks winning funds is actually worth → What a 50-year backtest reveals about the real role of bonds in your portfolio → The one thing the longest-living retirees have that most retirement plans ignore By the end, I think you'll feel even more confident in the patient, disciplined, evidence-based approach we talk about so often on this show. And, if nothing else, you'll walk away with a few new stats and stories worth sharing the next time markets come up in conversation. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| Retirement Replay: The Five Things Happy Retirees Have in Common | 30 juin 2026 | 00:13:19 | |
A strong financial plan can tell you whether you can retire, but it may not tell you whether you'll feel ready. In this Retirement Replay, behavioral finance expert and psychologist Dr. Daniel Crosby explains why retirement is not just a portfolio decision. He shares the five areas happy retirees tend to prepare for, why purpose and connection matter more than many people realize, and why even people with plenty of money can still struggle to make the leap. About Retirement Replay: After select guest interviews, we pull together the most replayed moments from the full conversation—the ideas listeners found valuable enough to rewind, revisit, or hear again. It's a quick way to catch the highlights or return to the takeaways that stood out most. Listen to the full episode: https://www.youstaywealthy.com/289 *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| Why $4M Still Doesn't Feel Like Enough to Retire (Listener Q&A) | 25 juin 2026 | 00:43:18 | |
At 63, David has $4 million saved. Two advisors have told him he's ready to retire, and every Monte Carlo simulation agrees... but he still can't bring himself to do it. "I'm no longer being smart," he admits. "I'm just scared to pull the trigger." The uncomfortable part is that no number may fix this, because what's holding David back was never on the spreadsheet. In this episode, I'm joined by Daniel Crosby, Ph.D. — a psychologist and behavioral finance expert — to answer listener questions about the part of retirement the math can't solve. You'll learn: → How to spend in retirement so the enjoyment doesn't wear off so fast → A 3-part framework for putting your money where it creates the most happiness → When changing your plan is wise, and when it's just reacting to noise → The 2 questions to ask when you're financially ready but still can't pull the trigger → What actually moves the 40% of your happiness that's within your control By the end, you'll have a clearer way to separate a plan that works on paper from a retirement you actually feel ready to live. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| Why Investors Bet 65% on a Familiar Fund Name (Even When the Investments Are Identical) | 18 juin 2026 | 00:21:13 | |
Imagine I hand you two mutual funds and ask how you'd split your money. Same holdings. Same cost. Line by line, they're the exact same fund. The only difference? One has a name you recognize and the the other is generic. Financially, there's no reason to prefer one over the other. But when researchers ran this experiment, investors didn't split their money evenly. In this episode, I break down new research on the hidden cost of making investment decisions based on familiarity. Here's what you'll learn: → Why a familiar fund name changes how investors judge risk, return, and safety → What the "trust premium" reveals about how investors value familiarity → How famous fund families have performed against their benchmarks → The questions to ask before choosing a fund or accepting an advisor's recommendation By the end, you'll have a more disciplined and informed way to judge whether confidence is being earned or merely assumed. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| Why Saving for Your Future Self Won't Buy a Better Retirement (And What Will) | 11 juin 2026 | 00:43:48 | |
You spend 30 or 40 years protecting your future self. Then you finally retire... and the person you were saving for never quite arrives. There's always an older version down the road who still feels like they need protecting. So you keep saving for tomorrow while postponing the life you could enjoy today. But more money for "future you" isn't what makes retirement better. In this episode, Hal Hershfield, Ph.D. — a UCLA professor of Behavioral Decision Making and author of Your Future Self — joins me to explain why. Here's what you'll learn: → Why your brain treats your future self like a stranger (and how that shapes every money decision) → How "projection bias" distorts irreversible choices like when to retire or claim Social Security → The "denominator problem" that stops retirees from spending + a simple reframe to help The distance we feel from our future selves is real and well-documented. It is also, with the right perspective, something we can learn to close. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| The 3 Questions That Reveal Your Real Inflation Risk in Retirement | 04 juin 2026 | 00:18:56 | |
When inflation makes headlines, it can feel like one of those retirement risks you just have to endure. Saving, investing, tax planning, income strategy... those are levers you can pull. Rising prices feel different. They feel like something that happens to you. But the inflation number you see in the news is rarely the number that matters most for your retirement plan. Two retirees can live through the same inflation environment and face very different risk — and the gap between them often comes down to a few things they can actually control. In this episode, I'm simplifying how retirement savers should think about inflation. You'll learn: → The 3 questions that reveal your true inflation risk → Why headline inflation can mislead retirees in both directions → How to protect your income, spending power, and retirement confidence A strong retirement plan doesn't require a perfect inflation forecast. It just needs to be built for the reality that uncomfortable periods will happen, and prepared for them before they arrive. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| 5 Umbrella Insurance Mistakes That Leave Retirement Savers Exposed | 28 mai 2026 | 00:30:20 | |
Umbrella insurance isn't usually the first thing people think about when they picture retirement planning. Most conversations focus on saving enough, investing well, reducing taxes, and creating income. But in retirement, one unintentional accident can create a very different kind of risk. Not just a temporary setback, but a threat to savings you may no longer have decades to rebuild. In this episode, I'm simplifying how umbrella insurance works for retirement savers. Specifically, I'm sharing: → Why liability risk doesn't necessarily disappear after your working years → What umbrella insurance does and doesn't cover → 5 common mistakes people make when buying or reviewing a policy → A simple 4-part formula for estimating how much coverage you actually need You'll also learn why the common "match coverage to net worth" rule can be misleading + why coverage may still make sense even when the math says you don't technically need it. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| Why 2 Retirees With the Same $1M Plan Ended $3M Apart | 21 mai 2026 | 00:23:40 | |
Two retirees. Same $1 million portfolio. Same 60/40 allocation. Same 4% withdrawal rate. Same 30-year retirement. The only difference? One retired in 1973. The other retired in 1975. Fast forward 30 years: one finished with about $280,000 and the other finished with over $3 million. Same plan. Just two years apart. In this episode, I'm breaking down new research that analyzes nearly a century of market history to answer a question most retirement plans don't spend enough time on: "How much does your exact retirement date shape the outcome of your plan?" Here's what you'll learn: → Why retirement timing may matter more than your withdrawal rate or asset allocation → Why a larger nest egg at retirement has historically led to worse outcomes → A 3-part playbook, in priority order, for protecting your plan when the starting point looks unfavorable Most retirement strategies focus on what happens after you retire. But this research suggests the year you walk away from work may deserve a much bigger seat at the planning table. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| The Real Reason Wealthy Retirees Still Wake Up Anxious (And the 4 Pillars That Fix It) | 14 mai 2026 | 00:20:31 | |
Many retirement savers assume the anxiety will lift once they hit a certain number. Maybe it's $1 million. Maybe $2 million. Maybe $5 million or more. And then the account crosses the line, the headlines turn ugly, and the worry is still there. A recent Wall Street Journal headline put it bluntly: "Even Rich Retirees Fear Outliving Their Money." In this episode, I'm sharing new research from Fidelity that helps explain why having "enough" so often still doesn't feel like enough. I'm also sharing the four things I consistently see in retirees who feel genuinely secure. Here's what you'll learn: → The retirement planning factor that more than doubles confidence → A cognitive concept that explains why retirement anxiety has very little to do with your account balance → The question many well-prepared retirees still can't answer — and why ignoring it can be so costly Not one of the four pillars has anything to do with the size of your portfolio. Which raises the real question: what's actually keeping wealthy retirees up at night? *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| Why Waiting Until 70 for Social Security Can Backfire (And the Question to Ask Instead) | 07 mai 2026 | 00:15:07 | |
The math behind "wait until 70" for Social Security is real. Hold off claiming from 62 to 70 and your monthly benefit climbs by roughly 77%. So why would anyone walk away from a number that big? The short answer is that the standard break-even analysis only measures one variable. And for retirees with healthy pre-tax savings, there are other factors at play that can make "waiting" a more expensive decision than it looks. In this episode, I'm turning the mic over to Josh Rendler — a partner at our firm — who walks through a case study of a 62-year-old woman with a $1.5 million IRA and the question most retirees are wrestling with. Here's what you'll learn: → The reframe that makes "wait until 70" fall apart for retirees with healthy pre-tax balances → How Social Security timing and Roth conversions compete for the same bracket space (and why claiming earlier can actually EXPAND your conversion runway) → The planning window that opens at 61, and what gets harder to fix once it closes The biggest claiming-age check isn't always the biggest after-tax outcome. And a well-built plan shouldn't make you choose between doing the math right and actually enjoying the retirement you spent 35 years earning. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| 3 Things to Review on Your Tax Return (And a Fresh Take on Social Security Timing) | 30 avr. 2026 | 00:40:23 | |
Tax season is finally over. The returns are filed, the stress is behind you, and the last thing you probably want to do is think about taxes again. But the weeks right after tax season are one of the most valuable windows you have all year. Every number from last year is fresh, every missed opportunity is still visible, and every mistake you just uncovered is a clue about what to fix going forward. In this episode, I sit down with Josh Rendler, CFP®, a partner at our firm and someone who spends his days deep inside client tax returns. Together, we're answering some of the biggest questions we're hearing from retirees right now. Here's what you'll learn: → The 3 numbers on last year's return that reveal your biggest 2026 planning opportunities → How to know if charitable giving belongs in your plan (plus the QCD detail that keeps it "invisible" to the IRS) → A fresh, counterintuitive take on Social Security timing While last year's return is still on your desk: what's hiding in there that could make 2026 better? 🤔 *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| The Most Overlooked Retirement Decision (It's Not Your Portfolio) | 23 avr. 2026 | 00:21:50 | |
One of the biggest decisions you'll make in your 70s and 80s has nothing to do with your portfolio. It's not about Social Security timing. And it's not about Roth conversions. It's about where you'll live and, more importantly, how care will be delivered, coordinated, and paid for if your health changes later on. Most people think of this as a lifestyle decision. But in reality, it's a housing-and-care decision, and it's one most retirement plans barely address. In this episode, I'm breaking down the later-life housing choices most retirement savers haven't fully thought through. Here's what you'll learn: → The four main housing options later in life—and how they differ in cost, care, and flexibility → What Continuing Care Retirement Communities (CCRCs) actually are (+ a little-known tax planning tip) → The four types of risk every housing decision really involves → When this decision usually needs to be made, and what can happen if you wait too long Because "we'll just stay in the house" isn't a plan...it's an assumption. And assumptions tend to get tested at the worst possible moment. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| The 6-Digit Code That Can Drain Your Retirement Account (And How to Stop It) | 16 avr. 2026 | 00:19:15 | |
According to the FBI, Americans lost nearly $21 billion to cyber-enabled fraud last year—a 26% increase from the year before. And the single largest category? Investment-related fraud, with more than $8.6 billion in losses. But what's most unsettling isn't the scale... it's how simple some of these scams really are. A retired couple recently lost thousands of dollars from their IRA after a scammer tricked them into sharing a single six-digit verification code over the phone. No hacking. No stolen password. Just one text message and one phone call. In this episode, I'm breaking down how "account takeover" scams work, why they're so effective, and the specific steps you can take to close the security gap. Here's what you'll learn: → The 3-step pattern behind most account takeover scams → Why your personal information may already be compromised (and what that means for your account security) → What to do—and what not to do—when a financial institution contacts you about suspicious activity → 3 simple upgrades to better protect your accounts that most people overlook In a world where scammers only need a few seconds to strike, your ability to slow down and take back control of the moment may be the most valuable layer of protection you have. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| The Real Cost of a Financial Advisor (And Why the 1% Math Is Misleading) | 09 avr. 2026 | 00:23:13 | |
A viral claim keeps making the rounds: that a 1% advisory fee will drain hundreds of thousands of dollars from your retirement savings. The math looks alarming... and that's exactly the point. But as with most things in finance (and life!), the truth is more nuanced than a headline or social media post makes it seem. In this episode, I break down research from Derek Tharp, Ph.D., CFP®, that puts this widely shared math to the test and reveals where it falls apart. Here's what you'll learn: → The misleading assumptions behind the popular "1% fee" calculation → How alternative fee models can be 3x more expensive using the same math → What academic research says about quantifying the value of a good advisor → A smarter way to evaluate whether hiring an advisor makes sense for your specific situation This episode isn't about defending any particular fee model. It's about making sure you have the right information to evaluate the cost, the value, and the role financial advice may play in your retirement planning. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| Why the Happiest Retirees Spend Their Money Differently | 02 avr. 2026 | 00:35:20 | |
Saving for retirement is one challenge. Feeling comfortable (and confident) enough to actually enjoy it is another. Even when the numbers say you're okay, uncertainty about the future can make it hard to use money for the things that matter most. Today, I'm revisiting a conversation with Dr. Daniel Crosby where we talk about money, happiness, and why spending is often harder than saving. It's especially relevant for me as my family currently navigates some big financial decisions... and a birthday trip for my oldest son that almost didn't happen. 🫣 In this episode, we discuss: → What the research gets wrong about the link between money and happiness → Why certain types of spending leave a bigger impact than others → A simple mindset shift that can make spending feel safer in retirement → What people near the end of life rarely regret—and what they wish they had done more of This conversation is a good reminder that money is a tool, and the goal is to use it to support the life you truly value. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| Why 59% of Stocks Destroy Wealth (And What Smart Retirees Do About It) | 26 mars 2026 | 00:19:33 | |
If you're in or near retirement, one bad investment decision can have lasting consequences. And new research shows just how risky stock picking can be: Over the last 100 years, nearly 60% of all U.S. stocks underperformed Treasury bills—one of the safest investments you can own. Even more surprising, fewer than 4% of companies created all of the stock market's net wealth. In other words, the odds of consistently picking the right stocks are far lower than most people realize. In this episode, I'm breaking down this eye-opening research and what it means for protecting your portfolio and retirement plan. Here's what you'll learn: → Why owning a handful of well-known, familiar stocks can be far riskier than it feels → What the research reveals about where long-term market returns actually come from → The 3 actions you can take to better position and optimize your portfolio for the years ahead Because in retirement, successful investing isn't about hitting home runs—it's about avoiding unnecessary mistakes and stacking the odds in your favor. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| The Roth Conversion Rule Almost Nobody Explains Correctly (4 Scenarios That Make It Simple) | 19 mars 2026 | 00:19:20 | |
Now that the One Big Beautiful Bill Act has made the 2017 tax rates permanent, more retirees are taking a fresh look at Roth conversions. But there's one rule that even reputable sources struggle to explain clearly—and the confusion can lead to costly mistakes. In this episode, I'm simplifying the Roth conversion 5-year rule and sharing: → Why the rule is so confusing (and what most people get wrong) → The fastest way to determine how the rule applies to your specific situation → 4 real-world scenarios so you can see exactly how it works If Roth conversions aren't a fit today, I'm also sharing one simple step everyone can take right now to make future conversions much easier. *** 📝 GRAB THE ROTH 5-YEAR FLOWCHART (PDF) Want to apply what you learned in this episode to your unique situation? Subscribe to the Stay Wealthy Retirement Newsletter and I'll send you my freshly updated Roth 5-Year Flowchart (PDF). It's a simple guide to help you navigate this tricky rule step by step. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| 5 Withdrawal Strategies to Boost Retirement Income (And How High You Can Really Go) | 12 mars 2026 | 00:29:13 | |
📝 Note: The 6.5% withdrawal rate is based on an 80% stock portfolio, a 30-year time horizon, and a 90% "confidence score." Thanks for your patience while we update the episode to include that information. ~Taylor *** Most people spend far less in retirement than they likely could. In fact, one study found married households age 65+ with more than $100k in savings withdrew just 2.1% per year on average. And ironically, the traditional 4% rule may be one reason why. In this episode, I'm breaking down new research on retirement withdrawal strategies—and what it reveals about how retirees may be able to spend more. Here's what you'll learn: → 5 strategies that (safely) support higher retirement income → The overlooked key to sustainable and confident retirement spending → 3 factors that can push starting withdrawal rates to as high as 6.5% The goal of retirement planning isn't just making your money last…it's making sure you actually use it. Which raises an important question: "Could you afford to spend more in retirement than you think?" *** 📆 BOOK A CALL: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| Why Healthcare Before Medicare Shouldn't Stop You From Retiring Early | 05 mars 2026 | 00:27:00 | |
Health insurance is keeping millions of Americans stuck in jobs they'd otherwise leave. In fact, 1 in 5 workers ages 50–64 say they're staying put because of their employer health coverage. And with recent changes to the ACA, that pressure is only growing. In this episode, I cover: → Why healthcare before Medicare has become a psychological roadblock to early retirement → Why the real cost of waiting until 65 may not be what you think → The options many people overlook and the tradeoffs worth understanding Because for most people, the healthcare challenge does have a solution. And the worst thing you can do is never explore your options at all. *** 📆 BOOK A CALL: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| The Retirement Income Mistake That Costs Investors Up to 6% Per Year | 26 févr. 2026 | 00:19:49 | |
For 30 or 40 years, a paycheck simply showed up. Then one day, it stops. Now you're staring at a portfolio and asking: "How do I turn this into reliable income for the rest of my life…without overpaying the IRS or outliving my money?" It's no surprise so many retirees gravitate toward dividends. They feel like a replacement paycheck. In fact, the majority of investors say they prefer dividends and interest over capital gains to fund retirement. But retirement income planning isn't just about generating cash flow. It's about creating sustainable income from a finite pool of capital while coordinating taxes and the rest of your retirement plan. In this episode, I break down new research on dividend investing and explain why the most popular income strategy may be far less efficient than it appears. I also share what the evidence suggests about building a portfolio and a plan that actually supports long-term retirement success. Because when it comes to funding your retirement, small structural decisions compound into very large outcomes. *** 📆 BOOK A CALL: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| The Retirement Risk That Changes Everything | 19 févr. 2026 | 00:14:31 | |
Markets move every day. Headlines change every hour. But the greatest threat to your retirement plan isn't volatility... it's something far less visible. In this episode, I'm breaking down: → The three components of risk most investors focus on (and the one they ignore) → Why rare, extreme events have an outsized impact on long-term wealth → How to build a retirement plan designed to survive (and even benefit from) uncertainty I'm also sharing why many "downside-protection" strategies sound compelling in theory, but are risky and difficult to execute in the real world. *** 📆 BOOK A CALL: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. *** EPISODE RESOURCES: | |||
| Why a Stock Market Crash Won't Ruin Your Retirement (and What Actually Will) | 12 févr. 2026 | 00:16:58 | |
Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. See how they fit together in one coordinated strategy built around your numbers. ----- Strong rallies make people uneasy. So does the fear that one bad crash could undo decades of careful saving. Recently, Morningstar published a great article centered around a chart mapping nearly 100 years of U.S. market history. When you zoom out, several widely accepted beliefs about market crashes and bull markets start to look far less certain. In this episode, I break down the three common myths the article explores. I also share what the data actually tells us about bear markets and what's far more likely to derail your retirement than a crash. Not to predict the future or eliminate risk. But to help you think more clearly about the environment we're in and how it fits into a disciplined, long-term retirement plan. ----- EPISODE RESOURCES: | |||
| Annuities Explained: When Guarantees Help—and When They Hurt Your Retirement | 05 févr. 2026 | 00:29:19 | |
Annuities are often sold as a simple solution to a complicated retirement problem. Guaranteed income. Protection from market volatility. Peace of mind that your money won't run out. But behind those promises is a much more complex set of trade-offs that many investors don't consider. Because while annuities can play a role in retirement planning, evaluating them in isolation often leads to unintended consequences (higher fees, reduced flexibility, extra taxes). So in today's episode, I break down how annuities actually work. We'll walk through the major types of annuities, how "guarantees" are structured, what you're really paying for, and where the risks tend to show up later in retirement. I'll also explain when annuities may make sense, when they don't, and how to evaluate them as part of a coordinated retirement plan so you can make informed decisions with confidence. *** 📆 BOOK A CALL: For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: | |||
| The Best Investment for Your Retirement (It's Not What You Think) | 29 janv. 2026 | 00:20:19 | |
What makes an investment "good?" It seems like a straightforward question, but the answer is more subjective than most people realize. Recently, my wife asked why I thought real estate was such a BAD investment when others she knows call it the BEST they've ever made. Hearing it framed that way struck a different chord. And rather than quickly defending my position with data and facts, I found myself reconsidering the question entirely. In today's episode, I share how to evaluate investments in the real world, what separates good investments from bad ones, and why some popular metrics can mislead. If you've ever wondered why an investment looks great paper but doesn't feel right—or why others swear by strategies you'd never touch—this episode will give you a clearer framework for thinking about your own portfolio. *** 📆 BOOK A CALL: For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: | |||
| What Happens to Your Taxes When a Spouse Dies (And How to Plan Ahead) | 22 janv. 2026 | 00:17:01 | |
After decades of filing taxes together, most couples assume their retirement plan will continue largely unchanged if one spouse passes away. But for many surviving spouses, the first surprise is a higher tax bill, even when income hasn't changed much. In this episode, I explain how a feature of the tax code can increase taxes after the loss of a spouse. Using a real-world example, I show why tax brackets shrink, why retirement income often doesn't, and how that mismatch can quietly drive taxes higher over time. More importantly, I share a planning framework couples can use while both spouses are still alive. We'll cover common mistakes, why the "married window" matters, and how small, intentional decisions made years in advance can meaningfully protect the surviving spouse. This isn't about fear or worst-case scenarios—it's about avoiding unnecessary surprises and making thoughtful, proactive decisions that support confidence throughout retirement. *** 📆 BOOK A CALL: For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: | |||
| How to Use 2026 Market Outlooks to Plan for Retirement | 15 janv. 2026 | 00:19:37 | |
Every year, Wall Street rolls out its market predictions. Targets get published, expectations get set, and the headlines make it sound like the future is just a spreadsheet away. But markets have a long history of humbling even the most confident forecasts, and that creates a real problem for retirement savers. Because, while short-term forecasts are usually noise, ignoring market expectations altogether isn't the answer either. So in today's episode, I break down how to think about market outlooks the right way. We'll cover why forecasts so often miss the mark, when long-term assumptions actually matter, and how market research can be used as a planning tool (not a prediction engine). I also share key themes from Vanguard's Economic and Market Outlook for 2026, focusing on growth, inflation, and expected returns—and why all of that matters for your portfolio and retirement plan. *** 📆 BOOK A CALL: For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: | |||
| 2026 Tax Changes Explained (Including 2 Rules Causing Confusion) | 13 janv. 2026 | 00:20:29 | |
Every January, we go through the same routine. Limits adjust, brackets shift, and most years it's just a quick refresh. But 2026 is different. Sweeping tax legislation passed last summer is introducing some of the biggest changes we've seen in a while. And buried inside those updates are two new rules that have already caused widespread confusion (even among experts). In this bonus episode, I walk through the most important tax updates for 2026 and explain why they matter for your retirement plan. I also also break down those two unique rules, sharing how they work, who they apply to, and why they matter. So even if you feel up to speed on the 2026 changes, I'm confident you'll walk away with at least one new and useful insight. *** 📆 BOOK A CALL: For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: | |||
| The 7 Questions That Shape a Confident Retirement | 08 janv. 2026 | 00:16:04 | |
After decades of saving and doing the right things, most people expect retirement to feel clear. But for many, it doesn't. Not necessarily because they didn't save enough, but because key financial decisions were made in isolation. In this episode, I walk through the seven questions every retirement saver should be able to answer. I also share the exact planning framework my team and I use to make sure those questions are addressed in a thoughtful, coordinated way. By the end of today's episode, you'll have a clearer framework for evaluating your retirement decisions. And more importantly, you'll understand what it actually takes to feel confident about the years ahead. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. *** EPISODE RESOURCES: | |||
| 7 Investing Facts Every Retirement Saver Needs to Hear | 18 déc. 2025 | 00:25:21 | |
It's that time of year again—time to step back from the complex tax strategies, Roth conversion debates, and retirement planning deep dives… and have a little fun. 😊 In this annual "surprising stats" episode, I'm sharing 7 counterintuitive facts about the markets and investing. Some are counterintuitive. A few might make you question things you've believed for years. And at least one involves math that should make anyone considering complex insurance products hit the pause button. By the end of today's episode, you'll walk away feeling more confident in the proven (sometimes boring!) academic approach to investing that we talk about so often here on the show. And if nothing else, you'll have a few holiday-dinner stats to drop between bites of pie. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. *** EPISODE RESOURCES: → Join the Stay Wealthy Retirement Newsletter | |||
| 3 Tax Planning Strategies Most Retirement Investors Overlook | 11 déc. 2025 | 00:28:56 | |
💥 Download the freshly updated 2026 Tax Planning Cheat Sheet (PDF): www.youstaywealthy.com/cheatsheet *** Most year-end tax advice is generic... max out your 401(k), bunch your deductions, donate to charity. But for diligent retirement savers with healthy nest eggs, the real opportunities are more nuanced. In this episode, I break down three tax strategies that can help you avoid overpaying the IRS and reduce your lifetime tax bill. You'll learn how to evaluate whether each move makes sense for your situation, so you're making informed decisions rather than chasing aimless deductions. If you're nearing retirement or already there, this episode will help you close out the year with a clearer tax picture and a smarter plan for the years ahead. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Schedule a Call *** EPISODE RESOURCES: → Download the 2026 Tax Cheat Sheet → Join the Stay Wealthy Retirement Newsletter | |||
| "Happy Thanksgiving (Yes, Even the Jerks)": Wisdom from Warren Buffett | 27 nov. 2025 | 00:19:12 | |
The Oracle of Omaha is officially "going quiet." In a rare and deeply personal announcement, Warren Buffett published what appears to be his final press release to shareholders. This episode isn't about taxes, investing, or the latest market headlines. It's about how one of the most successful investors of all time is thinking about money, family, aging, and what actually matters when the scoreboard stops moving. In this Thanksgiving special, I break down: ▶ Why he chose to say this now (at age 95!) ▶ What retirement savers and investors can learn from his message ▶ How his parting wisdom can change the way you use your time and wealth If you've ever wondered what your future self might wish you'd paid more attention to today, this conversation is for you. Tune in for the deeper meaning behind Buffett's Thanksgiving sign-off ("yes, even the jerks") and what it reveals about redefining success in the second half of life. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Schedule Your FREE Strategy Session *** EPISODE RESOURCES: | |||
| The S&P 500 Trap: Why the "Safe" Choice Is Actually Risky for Retirees | 20 nov. 2025 | 00:19:27 | |
"Just buy the index." It's the simple advice that built your wealth and got you to the finish line. But here's what often gets overlooked: The strategy that got you to retirement won't necessarily keep you there. When you switch from saving to spending, the math changes. Suddenly, relying on a "simple" S&P 500 strategy exposes you to risks that didn't matter when you had a paycheck. In this episode, we cover: ▶ The Simplicity Trap: Why "decision fatigue" lures smart retirees into risky, overly concentrated portfolios. ▶ S&P 500 Reality Check: Why the "safe" default option is actually dangerous for your retirement income. ▶ The "Flatline" Defense: How to build a retirement portfolio that protects your purchasing power during downturns. ▶ Beyond Investing: How to align your investments, taxes, and legacy for true peace of mind. If you are approaching retirement and wondering if your "set it and forget it" strategy is enough to last a lifetime this episode is for you. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, my team and I have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Schedule Your FREE Strategy Session *** EPISODE RESOURCES: | |||
| Why Retirees Fear Running Out of Money — Even Though They Rarely Do | 06 nov. 2025 | 00:17:27 | |
Everyone fears running out of money in retirement—even millionaires. What most people don't realize is that research shows most retirees rarely spend down their savings. In fact, many actually see their wealth grow throughout retirement, even during some of the toughest markets in history. In this episode, we unpack: ▶ Why that happens ▶ What the data really says about retirement spending ▶ How to find the right balance between confidence and caution By the end, you'll see why most retirees worry far more than they need to, and how to feel confident spending your own money. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, my team and I have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Schedule Your FREE Strategy Session *** EPISODE RESOURCES: | |||