The Tom Dupree Show

Tom Dupree

Investing For Retirement.

  1. 3d ago

    Is the Fed’s Shake-Up Good for Your Retirement Income? | Dupree Financial

    Is the Federal Reserve’s New Shake-Up Good or Bad for Your Retirement Income? By Tom Dupree, Founder, Dupree Financial Group Short answer: it’s genuinely both, and which one matters more depends on whether your retirement income is built to keep pace with rising costs. New Federal Reserve Chair Kevin Warsh has launched a formal, five-part review of how the Fed operates — covering everything from how it talks to markets, to how it collects the inflation data that moves interest rates, to whether artificial intelligence is quietly reshaping the economy in ways the old playbook never anticipated. On this week’s episode of The Financial Hour, James Dupree, Mike Johnson, and Michael Dawahare sat in to break down what this shake-up actually means — and, more importantly, what it means for anyone relying on their portfolio to produce real, spendable income in retirement. Key Takeaways A new Fed chair is auditing the Fed itself — five task forces are reassessing communications, the balance sheet, data quality, and the inflation target. The Fed’s own bond portfolio carries an unrealized loss in the hundreds of billions — proof that duration risk applies to everyone, including the Fed. AI is cutting both ways on inflation — boosting productivity in some areas, raising input costs like memory chips in others. A tariff-driven price bump and true monetary inflation are not the same thing, and the difference matters for how policymakers respond. Income that doesn’t grow — money markets, CDs, old bonds — quietly loses ground to rising costs every year it sits still. Who Is Kevin Warsh, and Why Is He Changing How the Fed Operates? Kevin Warsh has been a student of the Federal Reserve for most of his career, and one of his first moves as chair was to launch five task forces to reassess the institution’s core functions: communications, balance sheet policy, data quality, productivity and jobs (including AI), and the inflation framework itself. According to CNBC’s reporting on the review, the task forces are directed to start from first principles and question existing practice rather than simply fine-tune it — Brown Brothers Harriman strategist Scott Clemons described the approach as “regime change, but in a velvet glove.” The philosophy behind it is simple: stop, assess, and pivot where needed — the same discipline any well-run company applies when a board challenges management on why things are done a certain way. Warsh is asking the Fed to do that to itself, publicly, for the first time in a long time. What Did the Federal Reserve Get Wrong in 2008 and 2021? To understand why this review matters, it helps to look at the Fed’s actual track record. In 2006 and 2007, as the housing market was cracking, the Fed’s regional offices were on record saying there was no housing problem. There was. Then, in the aftermath of the 2008 financial crisis, the Fed held interest rates near zero for over a decade — a policy commonly called ZIRP — creating what our team described on-air as a “wet blanket” over markets that made honest price discovery difficult. The more recent example is fresher: in 2021, as trillions in pandemic stimulus moved through the economy, the Fed described the resulting price increases as “transitory.” They weren’t. Prices rose at the fastest pace in decades, and by the time policy caught up, households had already absorbed the damage — a miss the current review is squarely aimed at preventing from happening again. Why Does the Fed Have a Balance Sheet Loss in the Hundreds of Billions? Source: Federal Reserve Bank of New York, System Open Market Account (SOMA) Annual Reports, 2022–2025. Here’s a detail that surprises a lot of listeners: the Fed itself is sitting on a large paper loss. During the zero-rate years, the Fed bought enormous quantities of bonds with very low coupon payments as part of a policy known as quantitative easing. When interest rates rose in 2022, the market value of those bonds fell — the same way any bond’s price falls when rates rise. According to the New York Fed’s own 2025 System Open Market Account report, the unrealized loss on the Fed’s securities portfolio stood at $844.2 billion at the end of 2025 — down from over $1 trillion the year before, but still historically enormous. The Fed can’t easily sell these bonds without disrupting the very bond market it’s trying to stabilize, so for now, it’s simply absorbing the loss. It’s a useful, if uncomfortable, reminder: interest rate risk doesn’t spare anyone — not even the institution that sets interest rates. The Reframe: What the Fed’s Own Mistake Teaches Retirees About Bonds Here’s the part of this story that doesn’t show up in the news coverage of Warsh’s review: the Fed’s $844 billion paper loss isn’t just a Washington curiosity. It’s a live demonstration of the exact risk that quietly erodes many retirement portfolios. The Fed bought long-duration bonds when rates were near zero, on the assumption that those rates — and the value of those bonds — would hold. They didn’t. If the most sophisticated balance sheet in the world can misjudge duration risk that badly, it’s worth asking whether a retirement plan built around the same assumption — that a fixed-rate bond bought today will still meet your needs in ten or fifteen years — is really as safe as it feels. A bond doesn’t know what a gallon of milk costs in 2035. It just pays what it promised to pay in the year you bought it. This is precisely why our firm’s approach leans on dividend-paying, financially strong companies rather than a bond-heavy “set it and forget it” allocation. A healthy company’s board can raise its dividend as costs rise — a bond’s coupon is frozen the day you buy it. The Fed just proved, at a scale of nearly a trillion dollars, what happens when income doesn’t adjust to a changing rate environment. Retirees don’t have the option of just holding to maturity and calling the loss “unrealized.” That gap has to show up somewhere in a household budget. Is Artificial Intelligence Good or Bad for the Economy? One of Warsh’s five task forces is specifically looking at how AI affects productivity and jobs, and our hosts see it as a genuinely mixed picture. On one hand, AI is already making certain kinds of work dramatically more efficient; our hosts pointed to real examples of complex technical projects being completed in a fraction of the time they used to take. Historically, technology has tended to be deflationary — it lowers the cost of producing things over time. On the other hand, the buildout of AI infrastructure is pushing some costs up right now — memory chips being a clear example, which in turn affects the price of consumer electronics. So the net effect on inflation isn’t a simple yes-or-no answer. It depends on which part of the economy you’re looking at, and over what timeframe. What’s the Difference Between a One-Time Price Increase and Real Inflation? This distinction came up repeatedly in the episode, and it matters more than it sounds. A tariff, for example, can raise the price of a specific good once — that’s a one-time adjustment, not ongoing inflation. True inflation, by contrast, is a monetary phenomenon: more money in the system chasing the same amount of goods and services, which pushes prices up broadly and persistently. Our hosts noted that both the current Fed and Treasury leadership seem comfortable with modest inflation as long as wages are rising faster — a meaningfully different posture than in years past, and one that, if it holds, could support the kind of broader economic growth the country hasn’t consistently seen since before the 2008 financial crisis. How Can Retirees Protect Their Income From Inflation? This is where the conversation gets most practical for anyone at or near retirement. Money markets, CDs, and bonds purchased years ago don’t adjust for rising costs — the income they produce today is the same as it was when you bought them, even as your expenses climb. That’s not a flaw in those tools; it’s simply not what they’re designed to do. An income approach built around dividend-paying, financially strong companies works differently. When the underlying businesses are healthy, they have the ability to grow their dividend payments over time — even during flat or difficult markets — because a board’s decision to raise a dividend is separate from where the stock market happens to be on any given day. That’s the mechanism our team described as the foundation of an inflation-aware retirement income strategy: income with the potential to rise, rather than income that’s frozen in place. Frequently Asked Questions Is a little inflation actually a good thing? Fed and Treasury leadership have signaled comfort with modest inflation as long as wages are rising at a faster rate. The concern isn’t inflation existing at all — it’s inflation outpacing the income people rely on to cover their expenses. Why did the Fed call 2021 inflation “transitory” when it clearly wasn’t? The Fed’s framework at the time treated the post-pandemic price spike as temporary, tied to supply chain disruptions expected to resolve quickly. Instead, inflation persisted and accelerated well into 2022, now viewed as one of the Fed’s most consequential misreadings. Does AI cause inflation or reduce it? Both, depending on where you look. AI-driven productivity gains tend to be deflationary over time, the way most technology has been historically. But the current buildout of AI infrastructure is pushing up costs in specific areas, like memory chips, in the near term. Why don’t bonds and CDs keep up with inflation? A bond or CD generally pays a fixed rate of interest set at the time of purchase. As the cost of living rises afterward, that fixed payment b

  2. Jul 3

    How Do Insurance Companies Make Money? Lessons for Retirement Investors.

    THE TOM DUPREE SHOW  |  PODCAST SHOW NOTES How Do Insurance Companies Make Money? Lessons for Retirement Investors The Tom Dupree Show  |  Dupree Financial Group  |  dupreefinancial.com  |  859-233-0400 Episode Description Tom Dupree, Mike Johnson, and Michael Dawahare open with a Charlie Munger parable about the difference between memorized information and true understanding, then apply that lens to the week’s market headlines. They cover how SpaceX’s move into the cellphone business is reshaping the investment case for Verizon and AT&T, why property and casualty insurance stocks quietly outperformed in June, and what “combined ratio” and investment float actually reveal about how insurers make money. The conversation closes with a candid look at reshoring and globalization, and a reminder that even familiar, reliable dividend payers deserve a fresh look when the competitive landscape shifts. “Information is table stakes now — everybody has the same information. What separates a good investment decision from a bad one is understanding.” Topics Covered •  How property and casualty insurance stocks quietly outperformed the market in June •  What “combined ratio” reveals about an insurance company’s underwriting discipline •  How insurance “float” works, and Warren Buffett’s disciplined approach to it •  Charlie Munger’s “chauffeur knowledge” parable and why it matters for investors •  SpaceX’s entry into the cellphone business and what it means for Verizon and AT&T •  Reading stock technicals: what a broken 200-day moving average signals •  Comcast’s spin-off of its media business and the market’s reaction •  The case for U.S. manufacturing reshoring and its ripple effects on commercial insurance •  Knowing when to trim a position that’s run up quickly, using Verizon as an example •  A candid conversation on globalization’s impact on American manufacturing towns Key Takeaways •  Combined ratio is a key health check. A combined ratio under 100 means an insurer is collecting more in premiums than it pays out in claims — a simple number that reveals whether underwriting discipline is paying off. •  Insurance companies can be quiet compounding machines. A disciplined insurer that prices its risk well collects a “float” — premium dollars it can invest — that can become one of the most powerful long-term wealth-building tools in a portfolio. •  Understanding beats information. Anyone can look up a stock’s numbers online — the real edge comes from understanding how a business, its competitors, and the broader market actually interact. •  Technicals matter alongside fundamentals. A stock breaking below its 200-day moving average, as Verizon did, is a signal worth watching — but it doesn’t replace a full evaluation of dividend, valuation, and long-term outlook. •  Outperformance can be a signal to trim, not just celebrate. When a holding runs up quickly, as Verizon did earlier this year, it may be time to take some profit and reassess valuation rather than assume the gains will continue. •  Watch how a thesis plays out in the data. Rather than assuming a trend like reshoring is correct, disciplined investors track whether the facts and market behavior continue to support it. •  Not every “safe” dividend payer carries the same risk today. Long-held positions can face new competitive threats, so it’s worth revisiting whether the original reasons you bought them still hold true. About The Tom Dupree Show The Tom Dupree Show is hosted by Tom Dupree, founder of Dupree Financial Group and a 47-year veteran of the investment business. Each episode covers the financial topics that matter most to retirees and those approaching retirement — in plain English, without the Wall Street spin. Dupree Financial Group is a fee-only, fiduciary Registered Investment Advisory firm based in Lexington, Kentucky. The firm manages separately managed accounts focused on income-generating, dividend-paying portfolios — no products sold, no commissions, no conflicts of interest. Past episodes are available at dupreefinancial.com under the Radio tab. Schedule a Complimentary Portfolio Review If you’re not sure whether your portfolio still reflects the reasons you first bought it, or whether new competitive and market forces have quietly changed the picture — we’ll take a look. No charge. No pressure. Just an honest conversation about what you own and whether it’s working for you. Call: 859-233-0400  |  Visit: dupreefinancial.com The post How Do Insurance Companies Make Money? Lessons for Retirement Investors. appeared first on Dupree Financial.

  3. Jun 28

    Staying Invested During Market Volatility: When to Hold and When to Sell

    THE TOM DUPREE SHOW  |  PODCAST SHOW NOTES When to Hold, When to Sell: Staying Invested Through Market Volatility The Tom Dupree Show  |  Dupree Financial Group  |  dupreefinancial.com  |  859-233-0400 Episode Description When markets get choppy, the instinct to move to the sidelines can feel overwhelming — but acting on that instinct often costs investors far more than the volatility itself. In this episode, Tom Dupree and Lead Advisor Mike Johnson walk through the discipline behind staying invested, explaining how Dupree Financial Group evaluates when to hold a position, when to trim, and when to walk away entirely. The conversation covers real examples from their current portfolio — including dividend-paying holdings, pipeline stocks, and a diesel engine company that became a quasi-AI play — to illustrate how valuation and income generation shape every buy, hold, and sell decision. Tom and Mike also explain why the firm carries a significant cash position right now, and what that signals about how they view current market valuations. “Income from the portfolio tilts the table in your favor — it puts time back on your side while you wait for price appreciation.” Topics Covered Why panic selling during volatility almost always harms long-term returns How dividend income changes the calculus on whether to hold or sell The difference between timing the market and assessing individual stock valuations Real portfolio decisions: oil companies, pipeline stocks, Kroger, and an AI-adjacent diesel play Why the firm is holding more cash than usual — and what it says about current valuations The perma-bull vs. perma-bear debate and why optimism is essential for long-term investors How a team-based investment approach produces better decisions than any single viewpoint Why most 401(k) holders don’t know what they own — and why that matters more than ever Key Takeaways Dividends give you staying power. When a holding generates consistent income, missing that payout by selling too early is a real cost. Income from your portfolio buys you time to wait out price swings without being forced to sell at the wrong moment. The market’s best days cluster around its worst ones. Nearly half of the 50 best market days over the past 30 years occurred during bear markets. Investors who exit to avoid the drops frequently miss the recoveries that follow within days. Valuation — not emotion — should drive selling decisions. Tom and Mike trim positions when the math no longer makes sense: oil company stocks trading 25% above where they were when oil prices were identical, or a grocery chain whose core margin driver is eroding. Logic, not fear, triggers the sell. You can’t time the market, but you can prepare for it. As investor Howard Marks has noted, the goal isn’t prediction — it’s preparation. Knowing what you own, why you own it, and at what price it becomes expensive puts you in a position to act with clarity rather than react with panic. Not all stocks are meant to be held forever. Some positions are designed to be traded; others are core long-term holds. Understanding the difference — and building that distinction into your process from the start — is what separates disciplined investing from guesswork. A cash position is itself a valuation statement. Dupree Financial Group currently holds a significant cash and bond allocation because valuations look stretched. That defensive posture has allowed the portfolio to perform comparably to fully-invested indexes while taking on meaningfully less risk. Know what you own. Many retirement investors hold mutual funds or target-date funds without understanding the underlying holdings. If price movements in your portfolio are a mystery to you, you’re letting emotions — not analysis — make your decisions for you. About The Tom Dupree Show The Tom Dupree Show is hosted by Tom Dupree, founder of Dupree Financial Group and a 47-year veteran of the investment business. Each episode covers the financial topics that matter most to retirees and those approaching retirement — in plain English, without the Wall Street spin. Dupree Financial Group is a fee-only, fiduciary Registered Investment Advisory firm based in Lexington, Kentucky. The firm manages separately managed accounts focused on income-generating, dividend-paying portfolios — no products sold, no commissions, no conflicts of interest. Past episodes are available at dupreefinancial.com under the podcast tab. Schedule a Complimentary Portfolio Review If you’re not sure whether your portfolio is built to generate income through market volatility — we’ll take a look. No charge. No pressure. Just an honest conversation about what you own and whether it’s working for you. Call: 859-233-0400  |  Visit: dupreefinancial.com Dupree Financial Group is an SEC-registered investment adviser. Registration does not imply a certain level of skill or training. The information presented is for educational purposes only and does not constitute investment advice. All investing involves risk, including the possible loss of principal. Past performance is not indicative of future results. Securities mentioned are for illustrative purposes only and are not a recommendation to buy or sell. Please consult a qualified financial professional before making any investment decisions. The post Staying Invested During Market Volatility: When to Hold and When to Sell appeared first on Dupree Financial.

  4. Jun 21

    When to Sell A Stock

    The Tom Dupree Show  |  Podcast Show Notes Buying a Stock Is Easy. Knowing When to Sell Is Everything. The Tom Dupree Show  |  Dupree Financial Group  |  dupreefinancial.com  |  859-233-0400 Episode Description Every investor knows how to buy a stock. But the moment that determines real wealth — or real loss — is the moment you decide to sell. In this episode of The Tom Dupree Show, Tom Dupree, Lead Advisor Mike Johnson, and in-house analyst James Dupree lay out the sell discipline that has guided Dupree Financial Group’s portfolios for decades, including what triggers a trim, what triggers a full exit, and why waiting for someone else to tell you to sell is one of the costliest mistakes in investing. The conversation covers the full range of situations investors face: growth stocks valued on revenue and margin guidance, dividend payers evaluated on current yield, bonds that raised red flags in a management meeting, and legacy holdings kept alive by emotional attachment rather than logic. The team also addresses taxes, risk profile management, dry powder strategy, and the very human pull of FOMO that causes investors to ride winners too long — and losers even longer. “Buying a stock is easy. Selling a stock — regardless of whether it’s up or down — is a lot harder to do.” Topics Covered ●  Why sell discipline is the foundation of a sound investment process — not an afterthought ●  Valuing growth stocks on revenue guidance and gross margin targets rather than earnings alone ●  How current yield signals when a dividend stock has priced in too much optimism ●  The role of FOMO and emotional attachment in holding positions too long ●  Real examples: Freddie Mac, WorldCom, Kraft Heinz, and a local company that went up 20x and back to zero ●  Trimming vs. full exits: how partial sales create dry powder for new opportunities ●  Tax-smart selling: harvesting losses, the 30-day wash sale rule, and gifting low-basis shares to charity ●  Risk profile management: why one position becoming overweight is itself a sell signal ●  Why Intel’s 26-year performance history is a cautionary tale about holding without a thesis ●  The danger of relying on a single analyst’s buy list — and getting no sell guidance when markets turn Key Takeaways ●  Have a sell target before you buy. When you purchase a stock, establish the price or valuation level at which you would be satisfied selling. If the stock blows past that target, revisit the thesis — don’t just let momentum make the decision for you. ●  Valuation drives both buying and selling. A great company at the wrong price is still the wrong investment. Conversely, a mediocre company can become a strong buy when it gets cheap enough. Regularly re-evaluate what you own against current valuations, not just original purchase logic. ●  Current yield is a sell signal for income stocks. When a dividend-paying stock rises sharply, its yield compresses. If a stock yielded 6.5% when purchased and now yields 3.4% solely because the price doubled, the market is pricing in a level of optimism worth locking in. Consider trimming. ●  Trimming creates options. Most sell decisions don’t have to be all-or-nothing. Taking partial profits — and parking proceeds in money market as dry powder — gives you the flexibility to redeploy into new opportunities when they appear without being fully out of a strong holding. ●  Watch your risk profile, not just your returns. If one position grows to become the largest holding in the portfolio due to price appreciation alone, that concentration is a risk even if the company is excellent. Rebalancing is not a sign of doubt — it’s disciplined portfolio management. ●  Don’t let outdated advice run your portfolio. Tom shared the story of a widow who refused to sell two stocks because her late husband said never to — leaving her with a 2.1% yield when a redeployment could have generated 7%. Circumstances change. Investment advice should too. ●  Emotions are the enemy of good sell decisions. FOMO causes investors to hold too long on the way up. Denial causes them to hold too long on the way down. An investment committee, a written thesis, and objective valuation metrics help counteract the emotional pull that derails individual investors. ●  Taxes are part of the sell equation. In taxable accounts, realized gains have a cost. Pairing gains with losses (tax-loss harvesting), utilizing the 30-day wash sale rule carefully, and gifting low-basis shares to charity are all legitimate tools to make selling more tax-efficient. About The Tom Dupree Show The Tom Dupree Show is hosted by Tom Dupree, founder of Dupree Financial Group and a 47-year veteran of the investment business. Each episode covers the financial topics that matter most to retirees and those approaching retirement — in plain English, without the Wall Street spin. Dupree Financial Group is a fee-only, fiduciary Registered Investment Advisory firm based in Lexington, Kentucky. The firm manages separately managed accounts focused on income-generating, dividend-paying portfolios — no products sold, no commissions, no conflicts of interest. Past episodes are available at dupreefinancial.com under the Radio tab. Schedule a Complimentary Portfolio Review If you’re not sure whether your current portfolio reflects a real sell discipline — or whether you’re holding things longer than you should be — we’ll take a look. No charge. No pressure. Just an honest conversation about what you own and whether it’s working for you. Call: 859-233-0400  |  Visit: dupreefinancial.com Dupree Financial Group is a Registered Investment Advisor (RIA) registered with the Securities and Exchange Commission. Registration does not imply a certain level of skill or training. The information presented on this program is for educational purposes only and does not constitute investment advice, a solicitation, or a recommendation to buy or sell any security. Investing involves risk, including the potential loss of principal. Past performance is not indicative of future results. Please consult with a qualified financial advisor before making any investment decisions. -->The post When to Sell A Stock appeared first on Dupree Financial.

  5. Jun 13

    Nike’s Fall: Leadership Lessons for Retirement Investors

    The Tom Dupree Show  |  Podcast Show Notes The Nike Cautionary Tale: What Happens When Leadership Loses Touch With Its Customers The Tom Dupree Show  |  Dupree Financial Group  |  dupreefinancial.com  |  859-233-0400 Episode Description Nike spent decades building one of the most recognized brands on the planet — the Swoosh, the Air Jordan, high-heat basketball shoes that consumers lined up for, and a presence in every major sporting goods retailer in the world. Then, in 2020, the company handed its future to a CEO who believed physical retail was a dying model, and what followed became a study in how quickly a great company can lose its way. Tom Dupree and analyst Michael Dawahare walk through the full arc of Nike’s rise and decline — from its origins in performance athletics to a stock that traded at $180 and has since fallen to around $44. They examine the strategic decisions that caused the damage, the board failures that let it compound, and what retirement investors can take directly from the story. “You cannot put your own lenses on the lenses of your customer — you have to ask how they see the world, not how you see it.” Topics Covered • How Nike’s origins in performance athletics shaped the brand — and why that foundation was eventually abandoned • The 2020 appointment of CEO John Donahoe and the pivot toward a direct-to-consumer distribution model • Why walking away from wholesale partners like Foot Locker and specialty running stores was a catastrophic miscalculation • How competitors — HOKA, On Cloud, New Balance, ASICS, and Brooks — filled the shelf space Nike gave away • The role of groupthink and board failure in allowing the strategy to continue long after warning signs appeared • The Jordan Brand challenge: what happens when a generational endorsement ages out with no succession plan • Nike’s attempted course correction, the arrival of new CEO Elliott Hill, and why recovery is proving harder than expected • The parallel between Nike’s story and retirement portfolio management: proven strategy, fundamentals, and the danger of chasing new models Key Takeaways • Know what your portfolio is actually built on. The moment Nike shifted focus from technical performance products, competitors filled the gap. The same risk applies when an investment strategy drifts from its core principles. • Never surrender your shelf space. Giving up distribution — or abandoning a proven income strategy during volatility — is almost impossible to reverse. Re-entry is rarely seamless. • Leadership bias is one of the most expensive mistakes in business. Donahoe was an outstanding digital executive who ran a physical consumer company through a digital lens. Bias in a CEO — or a portfolio manager — costs real money. • Boards exist to prevent catastrophic decisions. Most don’t. Nike’s board approved a strategy that effectively fired its wholesale customer base. Institutional oversight is only as good as the willingness to ask uncomfortable questions. • Consumer loyalty, once transferred, is remarkably sticky. Runners who switched to HOKA or On Cloud did not come back. When a customer finds something they prefer, you may have lost them for good. • Recovery takes far longer than the damage itself. Nearly two years into Elliott Hill’s tenure, Nike still cannot get traction. A few years of bad decisions can take a decade to undo — in business and in retirement portfolios. • Proven strategies deserve skepticism about replacement, not abandonment. When a new model sounds compelling, always ask: What is the process? Has it been tested? And who benefits when you believe in it? About The Tom Dupree Show The Tom Dupree Show is hosted by Tom Dupree, founder of Dupree Financial Group and a 47-year veteran of the investment business. Each episode covers the financial topics that matter most to retirees and those approaching retirement — in plain English, without the Wall Street spin. Dupree Financial Group is a fee-only, fiduciary Registered Investment Advisory firm based in Lexington, Kentucky. The firm manages separately managed accounts focused on income-generating, dividend-paying portfolios — no products sold, no commissions, no conflicts of interest. Past episodes are available at dupreefinancial.com under the Radio tab. Schedule a Complimentary Portfolio Review If you’re not sure whether your portfolio is built on the same principles Nike abandoned — proven strategy, staying close to what works, and never losing sight of the fundamentals — we’ll take a look. No charge. No pressure. Just an honest conversation about what you own and whether it’s working for you. Call: 859-233-0400  |  Visit: dupreefinancial.com Dupree Financial Group is a Registered Investment Adviser (RIA) registered with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or training. The information presented on this podcast is for educational purposes only and should not be construed as personalized investment advice. Past performance is not indicative of future results. Investing involves risk, including the potential loss of principal. Please consult a qualified financial professional before making investment decisions. The post Nike’s Fall: Leadership Lessons for Retirement Investors appeared first on Dupree Financial.

  6. Jun 12

    Hidden Fees in Mutual Funds & Annuities | The Tom Dupree Show

    Where Did My Returns Go? The Cost of Mutual Funds and Annuities The Tom Dupree Show | Dupree Financial Group | dupreefinancial.com | 859-233-0400 Episode Description Time Stamps 00:00 Keep Truckin Intro 01:31 Show Opens Fees 03:22 Mutual Fund Basics 05:46 Share Classes Loads 07:14 Portfolio Fee Transparency 10:05 Tax Drag Distributions 14:01 Constraints Versus Drift 16:29 Managed Accounts Example 21:16 Break Segment Promo 22:05 Inflation Market Pinch 26:09 Mutual Fund Fee Reality 26:38 Annuities Insurance Wrapper 27:27 Index Annuity Caps 30:20 Fixed Annuity Tradeoffs 32:27 Immediate Annuity Inflation 37:32 Commissions And Incentives 40:29 Counterparty Risk Warning 44:30 Final Portfolio Checkup Most investors look at their mutual fund statement, see a return number, and assume that’s the whole story. It isn’t. Fees are deducted before that return ever reaches your statement, which means you could be paying anywhere from a fraction of a percent to well over 1.5% a year without it ever showing up as a line item. In this episode, Tom Dupree and Mike Johnson explain exactly how those costs are built into your returns — and why two people holding what looks like the “same” mutual fund can actually be paying very different amounts. The conversation also digs into a real-world example involving a major fund family, where a change to share class minimums forced a wave of investors to realize years of embedded capital gains — and a hefty tax bill — all at once. From there, Tom and Mike shift to annuities, breaking down how index annuities, fixed annuities, and immediate annuities are each priced, where the commissions come from, and why the financial strength of the insurance company behind the contract matters just as much as the product itself. Whether you’re holding mutual funds inside a 401(k), an IRA, or a taxable account — or you’ve been pitched an annuity recently — this episode gives you the questions to ask before you invest another dollar. “If you don’t know what you own in your portfolio — and why — that’s the first thing worth fixing.” Topics Covered How mutual fund fees get absorbed into your net return instead of appearing as a separate line item The difference between A shares, C shares, and institutional share classes — and why the same fund can cost twice as much depending on which one you hold What a 12b-1 fee is and who actually receives it Why actively managed funds tend to carry higher expense ratios than index funds How capital gains distributions can create a tax bill on gains you never benefited from A real example of how a fund family’s share class changes forced unexpected tax consequences on shareholders Portfolio constraints versus portfolio drift, and why both can work against you Index annuities, fixed annuities, and immediate annuities — how each is structured and where the cost is hidden Why surrender charges exist and how they relate to commissions Counterparty risk: why the insurance company’s own investments matter to your guarantee Key Takeaways Your net return already has the fee built in. Mutual fund statements show what’s left after fees are deducted — not a separate fee line — so two investors holding what looks like the same fund can actually be paying very different amounts depending on share class. Share class matters more than most investors realize. One example discussed in the episode showed a global fund charging roughly 0.8% on its A shares versus 1.8% on its C shares — more than double, for the same underlying portfolio. Tax inefficiency can be just as costly as the stated fee. Because mutual funds are pooled investments, other shareholders’ buying and selling can trigger capital gains distributions you owe taxes on — even if you never participated in those gains. A fund’s holdings can drift far from what you originally bought. Without firm constraints, a manager’s strategy can shift significantly over a few years, leaving you holding something very different from what your original research showed. Annuities are mutual funds wrapped inside an insurance contract — and you pay for both layers. Whether it’s an index annuity’s capped participation rate or a variable annuity’s rider fees, the cost is built into the structure even when it isn’t itemized. Surrender charges exist largely to recoup the seller’s commission. Annuity commissions can run as high as 6–8%, and the multi-year surrender schedule helps the insurance company recover that cost if you withdraw early. The insurance company’s financial strength is part of what you’re buying. An annuity’s guarantee is only as good as the company behind it — and recent industry reporting has noted that some insurers are taking on more investment risk, including exposure to private credit, than before the 2008 financial crisis. Transparency is something you’re entitled to ask for. Whether it’s a mutual fund, an annuity, or a managed account, you have the right to know exactly what you own, what it costs, and where your income is coming from. About The Tom Dupree Show The Tom Dupree Show is hosted by Tom Dupree, founder of Dupree Financial Group and a 47-year veteran of the investment business. Each episode covers the financial topics that matter most to retirees and those approaching retirement — in plain English, without the Wall Street spin. Dupree Financial Group is a fee-only, fiduciary Registered Investment Advisory firm based in Lexington, Kentucky. The firm manages separately managed accounts focused on income-generating, dividend-paying portfolios — no products sold, no commissions, no conflicts of interest. Past episodes are available at dupreefinancial.com under the Podcast tab. Schedule a Complimentary Portfolio Review If you’re not sure whether the funds or annuities in your portfolio are quietly costing you more than you realize, we’ll take a look. No charge. No pressure. Just an honest conversation about what you own and whether it’s working for you. Call: 859-233-0400 | Visit: dupreefinancial.com Dupree Financial Group is a fee-only, fiduciary, SEC-registered Registered Investment Advisor. The information presented in this podcast is for informational and educational purposes only and should not be considered a solicitation for the purchase or sale of any security. Past performance is not indicative of future results. Investing involves risk, including possible loss of principal. Please consult with a qualified professional before making any financial decisions. The post Hidden Fees in Mutual Funds & Annuities | The Tom Dupree Show appeared first on Dupree Financial.

  7. Jun 7

    AI Infrastructure Stocks & Your Retirement Portfolio

    The AI Build-Out Is Real — And It’s Reshaping How We Invest for Retirement THE TOM DUPREE SHOW  |  PODCAST SHOW NOTES The AI Build-Out Is Real — And It’s Reshaping How We Invest for Retirement The Tom Dupree Show  |  Dupree Financial Group  |  dupreefinancial.com  |  859-233-0400  |  Air Date: June 6, 2026 Episode Description Something significant is happening in the markets, and it goes well beyond the daily headlines. On this episode of The Tom Dupree Show, host Tom Dupree sits down with in-house analysts James Dupree and Michael Dawahare to examine the accelerating AI infrastructure build-out — and what it actually means for investors who are at or approaching retirement. The conversation covers the bottleneck stocks driving extraordinary gains in data centers and memory chips, Canada’s surprise $1 trillion infrastructure pivot, and why software companies like Snowflake and ServiceNow are proving that AI complements rather than kills their business models. The team also addresses the ongoing Iran conflict, what oil futures markets are signaling, and why the sequence of returns — not average returns — is the number that retirement investors should be watching most closely. “Markets don’t drift up — conviction is what moves them higher. Right now, the conviction is building around AI infrastructure, and the fundamentals are finally starting to catch up with the story.” Topics Covered AI infrastructure bull case — why the fundamentals are finally catching up with the story Micron, data centers, and the bottleneck theme — the stocks supplying scarce components for the AI build-out Jensen Huang’s public endorsement of Marvell Technology — what a declaration like that signals to institutional investors Agentic AI explained — what it means for your phone, your business, and your portfolio Canada’s $1 trillion infrastructure pivot — global validation of the AI build-out thesis from an unlikely source Software stocks proving their staying power — how ServiceNow and Snowflake are showing AI and software can coexist How AI is already driving revenue gains — consumer companies reporting explosive results from targeted AI marketing The Iran conflict and oil futures — what prediction markets and WTI pricing are signaling about resolution Sequence-of-returns risk in retirement — why when your portfolio loses matters more than how much it earns on average Dupree Financial Group’s in-house research approach — knowing what you own and why, not just riding an index Key Takeaways The AI build-out thesis is getting real-world validation.  PMI data hit a four-year high this week, suggesting genuine economic activity is accelerating alongside AI infrastructure investment — not just market narrative. Bottleneck stocks carry both opportunity and serious risk.  Companies supplying scarce components for data centers have posted extraordinary gains, but volatility cuts both ways. Position sizing and portfolio context matter. Software isn’t dead — it’s adapting.  Snowflake and ServiceNow are reporting earnings that prove their platforms work alongside AI tools, not against them. Productivity gains, not replacement, is the emerging story. Global capital is aligning behind AI infrastructure.  Canada’s sharp $1 trillion policy reversal covering energy, data centers, and defense adds significant international weight to the same thesis driving U.S. markets. How AI gets monetized is still being figured out.  Business-to-business subscriptions and API-based usage models are the most likely path forward, but valuations remain stretched until earnings consistently catch up. Sequence-of-returns risk is retirement’s hidden danger.  A portfolio drop in year one of withdrawals — even if markets recover later — can permanently reduce the income your portfolio generates. Dividend-focused portfolios are built to absorb that risk. In-house research is how you truly know what you own.  Dupree Financial Group’s analysts study these sectors every day so clients hold positions they understand — not just exposure to the broadest index available. The Iran situation is complex, but markets are pricing in a resolution.  Oil futures for July through September are trading in the $70–$80 range, suggesting the futures market expects the conflict to ease — though the IRGC’s fractured structure makes certainty impossible.   About The Tom Dupree Show The Tom Dupree Show is hosted by Tom Dupree, founder of Dupree Financial Group and a 47-year veteran of the investment business. Each episode covers the financial topics that matter most to retirees and those approaching retirement — in plain English, without the Wall Street spin. Dupree Financial Group is a fee-only, fiduciary Registered Investment Advisory firm based in Lexington, Kentucky. The firm manages separately managed accounts focused on income-generating, dividend-paying portfolios — no products sold, no commissions, no conflicts of interest. Past episodes are available at  dupreefinancial.com  under the Radio tab. Schedule a Complimentary Portfolio Review If you’re not sure whether your retirement portfolio is built to generate income through market turbulence — or if you’re just riding an index fund hoping for the best — we’ll take a look. No charge. No pressure. Just an honest conversation about what you own and whether it’s working for you. Call:  859-233-0400   |   Visit:  dupreefinancial.com Dupree Financial Group is a Registered Investment Adviser (RIA) registered with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or training. The information presented on The Tom Dupree Show is for educational and informational purposes only and should not be construed as personalized investment, tax, or legal advice. Past performance is not indicative of future results. Investing involves risk, including the possible loss of principal. Please consult a qualified financial professional before making any investment decisions. The post AI Infrastructure Stocks & Your Retirement Portfolio appeared first on Dupree Financial.

  8. Jun 7

    I’m 55 and Behind on Retirement — Here’s What You Can Actually Do About It

    THE TOM DUPREE SHOW  |  PODCAST SHOW NOTES I’m 55 and Behind on Retirement — Here’s What You Can Actually Do About It The Tom Dupree Show  |  Dupree Financial Group  |  dupreefinancial.com  |  859-233-0400 Episode Description Turning 55 can trigger some hard questions about retirement — not regrets about the past, but real concerns about the present. Tom Dupree and Lead Advisor Mike Johnson tackle one of the most common questions they hear from new clients: What do you actually do when you feel behind? This episode lays out a practical, honest framework for evaluating where you stand, calculating how much income your portfolio needs to produce, and identifying the specific actions that can still make a real difference in the next ten years. The conversation covers the math behind 401(k) catch-up contributions, the income gap calculation that determines whether your retirement plan actually works, why your expenses matter more than your portfolio balance, and the critical difference between volatility as a friend during accumulation versus a threat during withdrawals. Real client examples ground the discussion — including retirees who thrived on $400,000 and others who struggled with far more. The episode closes with a clear message for anyone in their mid-50s who has been putting off this conversation: the opportunity is still real, the tools are available, and it starts with one step. At 55, you might feel like you’re late getting started — but you still have a lot of opportunity to build real wealth and retire the way that you want. Topics Covered The income gap: How to calculate the difference between your fixed income sources and what you’ll actually need to spend in retirement 401(k) catch-up contributions: The 2026 limits for savers over 50, including the super catch-up provision for ages 60–63 Real accumulation scenarios: What maxing out a 401(k) at a 6% return actually produces over 10 years — for one earner and two Expenses as the key variable: Why what you spend in retirement matters more than how much you’ve saved Wealth vs. riches: Why clients with $400,000 sometimes retire better than those with $2 million Sequence-of-returns risk: How early losses in retirement can permanently damage a portfolio — and why income investing helps avoid that trap The wealth paradox: Why taking on more risk when you’re close to your target number can do more harm than good Social Security strategy: Age 62 vs. full retirement age vs. 70 — and how to think about spousal benefits and break-even timing In-service rollovers: How to start building an income-producing portfolio while you’re still working and contributing How to prepare for your first meeting: What to bring, what to expect, and how the planning conversation actually works Key Takeaways Your expenses determine everything. The question isn’t how much you’ve saved — it’s whether what you have can cover the gap between your fixed income and your actual spending. Get clear on your expenses before anything else. Age 55 is still a strong position. You’re likely near peak earnings, kids may be off the payroll, and 401(k) catch-up rules let you contribute up to $32,500 a year — or $35,750 between ages 60 and 63. Ten years of disciplined saving can still produce meaningful income. Don’t ignore the employer match. Contributing at least enough to capture your employer’s match is a 100% guaranteed return from day one. There is no simpler, more powerful first move. Volatility is your friend while you’re accumulating — not when you’re withdrawing. During your working years, market swings let you buy more at lower prices. In retirement, a bad year early can force you to sell assets at the worst possible time. That’s the sequence-of-returns risk that ends retirement plans. Income portfolios solve a problem, growth portfolios don’t. When your portfolio pays you dividends and income, you don’t have to sell holdings to fund your lifestyle during down markets. That changes the entire risk equation. The wealth paradox: more isn’t always better if it requires more risk. If you already have the number that funds the retirement you want, adding risk for more upside isn’t rational — the downside threatens the entire plan, while the upside is just gravy. Social Security is a strategic asset, not just a check. Delaying from 62 to 70 can dramatically increase your lifetime benefit. The break-even point is roughly age 82, and a spousal benefit strategy can add another layer of optimization. You can start building income while you’re still working. An in-service rollover at age 59½ lets you move funds from your 401(k) into an IRA where they can be invested for income — so the income engine is already running when you retire. About The Tom Dupree Show The Tom Dupree Show is hosted by Tom Dupree, founder of Dupree Financial Group and a 47-year veteran of the investment business. Each episode covers the financial topics that matter most to retirees and those approaching retirement — in plain English, without the Wall Street spin. Dupree Financial Group is a fee-only, fiduciary Registered Investment Advisory firm based in Lexington, Kentucky. The firm manages separately managed accounts focused on income-generating, dividend-paying portfolios — no products sold, no commissions, no conflicts of interest. Past episodes are available at dupreefinancial.com under the Radio tab. Schedule a Complimentary Portfolio Review If you’re not sure whether your current savings and investments can actually close the gap between what you’ll have and what you’ll need in retirement, we’ll take a look. No charge. No pressure. Just an honest conversation about what you own and whether it’s working for you. Call:  859-233-0400   |   Visit:  dupreefinancial.com REGULATORY DISCLAIMER Dupree Financial Group is a Registered Investment Adviser (RIA) registered with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or training. The information presented on this program is for educational purposes only and does not constitute investment advice, a solicitation, or an offer to buy or sell any security. Past performance is not indicative of future results. Investing involves risk, including the possible loss of principal. Listeners should consult with a qualified financial professional before making any investment decisions. The post I’m 55 and Behind on Retirement — Here’s What You Can Actually Do About It appeared first on Dupree Financial.

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