The Tom Dupree Show

Hosted by Tom Dupree

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Jun 2026

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Investing For Retirement.

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June 13, 2026

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.

June 12, 2026

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.

June 7, 2026

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.

June 7, 202645 min

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.

May 29, 2026

What to Do When You Inherit Money: The Rules, the Risks, and the Right Moves

Episode · May 30, 2026 What to Do When You Inherit Money: The Rules, the Risks, and the Right Moves The Tom Dupree Show|Dupree Financial Group|dupreefinancial.com|859-233-0400 Episode Description Inheriting money should feel like good news — and it often is. But the moments surrounding an inheritance are rarely straightforward. There’s grief. There’s urgency. There’s a sudden responsibility for assets you didn’t plan for, invested in ways not designed for your situation. In this episode, Tom Dupree and Lead Advisor Mike Johnson walk through what actually happens when wealth transfers from one generation to the next — and what to do about it. The conversation covers the full spectrum of inherited assets: taxable investment accounts with stepped-up cost basis, life insurance proceeds, annuities with embedded tax liabilities, and the increasingly complicated world of inherited IRAs. Tom and Mike explain how the SECURE Act of 2019 effectively ended the stretch IRA, what the 10-year rule now requires of most non-spouse beneficiaries, and why failing to plan around required annual distributions can trigger a decade of preventable tax consequences. The episode also covers practical strategies for current asset owners — how to use appreciated stock gifts to rebalance efficiently, when to let a legacy holding ride to pass a stepped-up basis to heirs, and why having all parties (investment advisor, CPA, and attorney) on the same page before a transfer happens makes everything smoother. Knowing what you own and why you own it isn’t just good advice for volatile markets — it’s the foundation of a plan your heirs can actually build on. Topics Covered The gray wave: why trillions in wealth are changing hands over the next 15 years The 90-day rule: why pausing before making any major financial move protects you Stepped-up cost basis on inherited taxable accounts — how it works and why it matters Tax treatment differences between inherited IRAs, annuities, and life insurance proceeds The SECURE Act’s 10-year rule for inherited IRAs and required annual distributions Exceptions to the 10-year rule: spouses, minor children, disabled beneficiaries, and siblings within 10 years Using inherited IRA withdrawals to fund Roth conversions on your own accounts Gifting appreciated stock to charity as a tax-efficient rebalancing strategy Why beneficiary designations and estate coordination require regular review How Dupree Financial Group coordinates with CPAs and attorneys to quarterback inheritance planning Key Takeaways Pause before you act. An inheritance often arrives during an emotionally charged time. Waiting 90 days before making any major gifting, investment, or debt payoff decisions keeps emotion out of choices with long-term consequences. Not all inherited assets are taxed the same. Taxable investment accounts typically receive a stepped-up cost basis — wiping out embedded capital gains for the beneficiary. Life insurance proceeds are generally income-tax-free. Annuities and inherited IRAs carry ordinary income tax obligations. Knowing the vehicle determines the strategy. The stretch IRA is gone. The SECURE Act of 2019 eliminated the ability for most non-spouse beneficiaries to stretch inherited IRA distributions over their lifetime. A 10-year withdrawal window now applies, with required annual distributions each year — not just a lump sum in year ten. A withdrawal plan for an inherited IRA is not optional. The IRS requires distributions each year over the 10-year period. Without a coordinated strategy, beneficiaries can face unexpected income spikes, higher tax brackets, and lost reinvestment opportunities. Gifting appreciated stock beats gifting cash. If you plan to give to charity anyway, donating appreciated shares instead of writing a check eliminates the capital gain for you, produces no tax consequence for the charity, and frees up cash to repurchase the same investment at a higher cost basis. Beneficiary designations are the most overlooked planning tool. Outdated or missing designations create probate complications and can override your wishes entirely. Regular reviews — coordinated across investment accounts, retirement plans, and insurance — are essential. Coordination between advisors prevents costly mistakes. Inheritance planning sits at the intersection of investments, taxes, and legal structure. Having your financial advisor, CPA, and attorney aligned — not working in silos — is the difference between a smooth transition and a decade of cleanup. The income approach applies to inherited assets, too. Inherited portfolios that aren’t generating income need to be repositioned around your actual retirement cash flow needs. A growth-oriented portfolio you’ve inherited wasn’t built for your life — it needs to be evaluated in the context of your plan. 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 set up to generate income — whether you’ve recently inherited assets or simply want to know what you own and why you own it — 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 What to Do When You Inherit Money: The Rules, the Risks, and the Right Moves appeared first on Dupree Financial.

May 24, 202644 min

All-Time Highs and America’s Second Industrial Revolution

THE TOM DUPREE SHOW | PODCAST SHOW NOTES All-Time Highs and America’s Second Industrial Revolution The Tom Dupree Show | Dupree Financial Group | dupreefinancial.com | 859-233-0400 Episode Description Markets are hitting all-time highs in the spring of 2026, and Tom Dupree sits down with analysts Michael Dawahare and James Dupree to examine what is actually fueling the rally. The conversation goes well beyond the headlines — covering real earnings growth at AI infrastructure companies, a sweeping national push to bring critical industries back to American soil, and what the arrival of Kevin Warsh as the new Federal Reserve chairman could mean for bond markets and retirement investors. The team also takes a careful look at how to tell the difference between companies with genuine contracted revenue and those priced years into a speculative future. And in a segment that hits close to home for many Kentucky listeners, the hosts examine the structural forces reshaping the bourbon and spirits industry — from shifting generational attitudes toward alcohol to the surprising effect that GLP-1 medications are having on consumer behavior. “Markets don’t drift up — they only rise on conviction. Right now, that conviction is being written in the earnings reports and long-term contracts of the companies building America’s next industrial base.” Topics Covered Why markets are at all-time highs — and whether the earnings justify the rally AI infrastructure spending: hyperscalers committing close to one trillion dollars in 2026 Reshoring as national security strategy: six to eight industries America should stop outsourcing Separating real AI businesses from speculative plays priced years into the future Kevin Warsh as new Fed chairman: a smaller balance sheet and better price discovery in bond markets Historical midterm election pullbacks and what they may signal for the current market cycle Commodities as the most compelling derivative trade of the global reshoring movement GLP-1 drugs and generational attitudes reshaping the bourbon and spirits industry The dot-com bubble parallel: which AI companies have staying power, and which don’t How the COVID pandemic became the pivotal catalyst that accelerated reshoring across industries Key Takeaways Earnings are driving the highs, not speculation alone. Some AI infrastructure companies are reporting 500%+ year-over-year revenue growth backed by signed, long-term contracts. That is a meaningfully different foundation than the dot-com era provided. Know the difference between a business and a bet. Within the AI space, some companies hold 15-year leases and tens of billions in guaranteed revenue. Others are priced five years into an uncertain future with minimal earnings today. Understanding which type you own matters. Reshoring is a generational investment thesis. A coordinated government-and-industry effort to bring back pharmaceutical production, chip manufacturing, steel, aluminum, and energy creates real downstream opportunities in commodities, infrastructure, and labor. A smaller Fed could be good for markets. Kevin Warsh has signaled a desire to reduce the Fed’s balance sheet, which could restore honest price discovery in the bond market — a shift that ripples positively through stocks and other dollar-denominated assets. All-time highs historically lead to higher highs. New market highs on volume reflect the collective judgment of all participants. Pullbacks of 10 to 15 percent are healthy and expected, but they do not change the long-term direction for investors holding quality positions. The spirits industry faces headwinds that may not be temporary. Younger generations are beginning to treat alcohol the way prior generations came to view cigarettes. GLP-1 drug adoption is compounding that shift, with real implications for Kentucky’s economy. Commodities deserve a closer look. As countries reshore and protect the raw materials they need, global supply is tightening. Energy, metals, and materials could benefit from a sustained multi-year tailwind that many retirement portfolios are not currently positioned to capture. 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 is built for yesterday’s market — or whether it’s positioned for where things are actually heading — 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 All-Time Highs and America’s Second Industrial Revolution appeared first on Dupree Financial.

May 15, 202645 min

What to Expect When You Finally Call a Financial Advisor

THE TOM DUPREE SHOW | PODCAST SHOW NOTES What to Expect When You Finally Call a Financial Advisor The Tom Dupree Show | Dupree Financial Group | dupreefinancial.com | 859-233-0400 Episode Description For many people approaching retirement, the thought of calling a financial advisor triggers more anxiety than excitement. Will they judge what I have? Will I be pressured into something I don’t need? Do I even have enough to make the conversation worth anyone’s time? These concerns are common — and largely unfounded. The first meeting with the right kind of advisor starts with listening, not selling, and it opens with a question, not a pitch. “A good advisor does far more listening than talking — and if they’re doing all the talking, they’re probably selling something.” Tom Dupree and Mike Johnson walk through what that first conversation actually looks like at a fee-only, fiduciary firm: what to bring, how to think about your expenses and Social Security estimate, and what questions to ask about how the advisor is paid and what they actually invest in. There is no obligation at that first meeting — and there should not be. “The only thing your first meeting costs you is your time. You’re not signing anything, committing to anything, or obligating yourself to anything — just having a conversation.” The episode also covers the red flags worth watching for — urgency tactics, product pushes before any real analysis, advisors who can’t explain what they own or why — and what the path forward looks like if you decide to move ahead. The proposal meeting, the transfer process, and how ongoing reviews work are all covered in plain terms. “Almost without exception, people walk out of that first meeting saying they wish they’d done it sooner — whether they become clients or not.” Topics Covered Why so many people delay meeting with a financial advisor — and what actually holds them back What to bring to your first appointment: statements, Social Security estimates, pension documents, and more What really happens during the first meeting — and why a good advisor asks more than they tell How a fiduciary, fee-only firm approaches your situation differently than a commission-based one The key questions every investor should ask before agreeing to work with any firm Red flags to watch for: product pushes, urgency tactics, and advisors who can’t explain their holdings The difference between fee-based, commission, and hourly compensation — and why it matters for your money Why both spouses should be in the room from the very first conversation What comes next: the proposal meeting, the transfer process, and how ongoing reviews are structured Key Takeaways The first meeting is free — in every sense. No contracts, no commitments, no pressure. The only cost is your time, and most people leave having learned something they didn’t know walking in. Bring a few basics, not a perfect portfolio summary. Your most recent investment statements, a Social Security estimate from ssa.gov, a rough sense of monthly expenses, and any pension or life insurance documents you have handy are all you need. Ask directly: Are you a fiduciary? Not “do you put clients first” — ask the specific question and expect a clear yes. Vague answers like “we try to act in your best interest” are not the same thing legally. Understand how the advisor is paid. Fee-based, commission, and hourly structures each create different incentives. Knowing the difference helps you spot potential conflicts of interest before they affect your money. The advisor should be listening more than talking. A first meeting that feels like a presentation is a warning sign. The right firm wants to understand your situation — your goals, your income needs, your family — before recommending anything. Know who actually holds your money. A reputable firm uses an independent third-party custodian that is not affiliated with the advisor or the investment products they recommend. This separation exists by design. Bring your spouse from day one. Both partners should be part of the conversation from the start. Learning the details of the financial plan for the first time during a crisis is a situation worth preventing. Keep asking what they invest in — and why. An advisor should be able to explain every holding in plain terms. If they can’t — or if their answer is vague — that is worth paying close attention to. 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 retirement income strategy is built around what you actually need — 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 What to Expect When You Finally Call a Financial Advisor appeared first on Dupree Financial.

May 10, 202645 min

Reading the Market Through the Fog: AI, Iran, and Your Retirement

The Tom Dupree Show | Podcast Show Notes Reading the Market Through the Fog: AI Momentum, Iran’s Economic Shadow, and What It Means for Your Retirement Portfolio The Tom Dupree Show | Dupree Financial Group | dupreefinancial.com | 859-233-0400 | Air Date: May 9, 2026 Episode Description The market rarely moves in one direction for one reason, and this episode is a clear illustration of that. Tom Dupree, Mike Johnson, and James Dupree cover two very different forces shaping portfolios right now: the surging momentum in AI-related stocks — semiconductors, memory chips, and optical connectivity — and the slower-burning economic threat posed by the conflict in the Strait of Hormuz, which is putting pressure on oil prices, fertilizer supply, and the global food chain heading into planting season. The team breaks down what a gamma squeeze is and why it may be amplifying gains in certain tech stocks beyond what fundamentals alone would justify, what three scenarios for the Strait of Hormuz reopening could mean for inflation and interest rates, and how Dupree Financial Group thinks about making incremental portfolio adjustments without abandoning a long-term retirement income strategy. It is a candid look at the internal conversations that happen when managing real money in an uncertain world. “It’s like the duck on water — it looks calm on the surface, but underneath, its feet are going 100 miles an hour.” — Mike Johnson, on the market’s competing cross-currents “You can be right on a situation and still be wrong on the market — so you make incremental adjustments while keeping the baseline investment process the same.” — Tom Dupree Topics Covered What a gamma squeeze is — and why it may be inflating gains in AI-related stocks beyond their fundamentals The memory chip shortage: why demand for semiconductors from Micron and SanDisk is driving price surges and what it means for industries from gaming to AI Optical connectivity stocks and the supply bottleneck in pump lasers — why companies like Applied Optoelectronics and Lumentum Holdings are reporting explosive revenue growth Intel’s remarkable comeback: 26 years of flat performance, a new Apple partnership, and a US government stake that has turned into a six-bagger The Niall Ferguson framework: three Strait of Hormuz scenarios and their projected effects on fertilizer prices, crop production, energy costs, and global inflation Why fertilizer timing matters as much as price — and how the conflict’s overlap with planting season creates a different kind of risk than past supply disruptions Stagflation as a tail risk: what it would mean for long-duration assets including growth stocks and fixed income How Dupree Financial Group makes incremental portfolio adjustments — trimming positions that have performed well, adding exposure to areas of opportunity — without making all-or-nothing bets Why knowing what you own matters more than ever when markets are moving in multiple directions at once Fee transparency: what a single, straightforward advisory fee looks like compared to the layered costs many investors carry without realizing it Key Takeaways Market momentum can be real and artificially amplified at the same time. A gamma squeeze occurs when options market makers are forced to buy shares to hedge their positions as prices rise past certain strike levels. This mechanical buying can push prices higher faster than fundamentals alone would justify — and can reverse just as quickly. Understanding what is driving a move matters more than just watching the move itself. Memory chips are a genuine bottleneck in the AI buildout — and prices reflect it. The cost of one terabyte of memory roughly tripled in a matter of months as AI data center demand outpaced supply. Companies that make or depend on memory chips are seeing earnings growth that justifies valuations even after large price increases. This is not just momentum — there are real fundamentals underneath it. The Strait of Hormuz conflict is not just an oil story. Fertilizer — specifically urea — moves through the same strait, and urea prices rose roughly 47 percent in two months. With global planting seasons underway, a prolonged bottleneck affects crop yields for the full harvest year, which has downstream effects on food prices and inflation that take time to work through the system. Tail risks are worth considering even when they are not the base case. The hosts reference the 2008 housing crisis as a reminder that consensus thinking can be catastrophically wrong. Considering scenarios outside the mainstream — and thinking through their portfolio implications — is part of responsible retirement money management, even when those scenarios are unlikely. Stagflation is hard on long-duration assets — including growth stocks. In an environment of high inflation and rising interest rates, both long-duration bonds and high-multiple growth stocks are vulnerable. A portfolio built around dividend-paying companies with pricing power and predictable cash flows holds up better in that environment than one chasing price appreciation alone. Incremental adjustments beat all-or-nothing calls. The team trimmed positions that had run significantly and added exposure to areas of opportunity — not because they predicted the market bottom, but because valuations and fundamentals supported it. Timing the market perfectly is not the goal; managing risk and staying positioned for income is. Knowing what you own — and what it costs — is more valuable than most investors realize. Many people working with financial advisors cannot describe what is in their portfolio or how much they are paying in total fees. Dupree Financial Group charges one transparent fee, owns individual companies in each client’s separately managed account, and can explain every holding and why it is there. 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 to hold up in an environment like this one — with competing pressures from AI momentum, rising energy costs, and inflation risk — 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 Investment Advisory firm based in Lexington, Kentucky. This content is for informational and educational purposes only and does not constitute personalized investment advice. Nothing heard on this program is a recommendation to buy or sell any security. Past performance is not indicative of future results. Investing involves risk, including the possible loss of principal. Please consult a qualified financial advisor before making investment decisions. The post Reading the Market Through the Fog: AI, Iran, and Your Retirement appeared first on Dupree Financial.

May 10, 202645 min

Why Your Target Date Fund May Fail You in Retirement

TomDupreeShow_ShowNotes_2026-05-09 The post Why Your Target Date Fund May Fail You in Retirement appeared first on Dupree Financial.

May 3, 202644 min

Your 401(k) Is Not a Retirement Plan

Episode: The Tom Dupree Show | Host: Tom Dupree | Co-host: Mike Johnson Episode Summary Tom Dupree and Mike Johnson tackle one of the most common misconceptions in retirement planning: that a 401(k) balance is a retirement plan. It isn’t. It’s a savings vehicle — and a very good one — but it was designed to collect money, not distribute it. This episode explains what that distinction means in practical terms, and what steps to take before retirement to make sure your savings can actually do the job you’re counting on them to do. Topics Covered in This Episode Why a 401(k) is an accumulation vehicle, not a retirement plan The problem with applying a growth portfolio to a withdrawal strategy How rolling a 401(k) into an IRA opens up income-oriented investment options The three-legged stool: income, growth of income, and price appreciation Why selling shares to fund expenses works in a rising market — and fails in a flat or declining one The case for consolidating multiple old 401(k) accounts before retirement How dividend income shifts the focus from watching the balance to watching the cash flow Why pure asset allocation models limit flexibility in retirement The psychological value of knowing what you own and why you own it Key Takeaways The 401(k) did its job — now it needs a different tool. A 401(k) is structured for dollar-cost averaging and tax-deferred growth. That design is a poor match for generating predictable monthly income in retirement. A bigger balance is not a plan. Knowing your account value is not the same as knowing what that value will produce for you each month, for how long, and under what market conditions. Income-first investing changes the math. When a portfolio generates enough dividend income to cover living expenses, you are not forced to sell shares during market downturns — and that distinction is what protects long-term wealth. Rolling to an IRA opens up your options. The investment menu inside a 401(k) is limited by plan design. An IRA allows access to individual dividend-paying stocks and income-generating vehicles that most 401(k) plans don’t offer. Scattered accounts are a retirement hazard. The average person approaching retirement holds three to five old 401(k) accounts. Consolidating simplifies beneficiary designations, RMD calculations, and day-to-day management. Watch cash flow, not just the balance. In retirement, the number that matters most is what the portfolio produces each month — not what it’s worth on any given day. Know what you own and why you own it. Clients who understand their holdings don’t panic when markets get choppy, because they know the income side of the equation hasn’t changed even if the price has. Three Questions Worth Answering Before You Retire Tom closed the episode with three questions every listener should be able to answer: Do you know what fees you’re paying? Do you know what income your portfolio is currently producing? Do you know what you own and why you own it? If you can’t answer even one of those with confidence, that’s worth addressing before retirement — not after. Frequently Asked Questions What is the difference between a 401(k) and a retirement plan? A 401(k) is a tax-deferred savings vehicle offered through your employer. It is designed to accumulate money during your working years. A retirement plan is a personalized strategy that determines how you will generate income from your savings throughout retirement — including what you own, how much you withdraw, how taxes are managed, and how long your money needs to last. The 401(k) is one piece of that plan, not the plan itself. Should I roll my 401(k) into an IRA when I retire? For most retirees, rolling a 401(k) into an IRA makes sense because an IRA offers a much wider range of investment options — including individual dividend-paying stocks and income-focused strategies that most 401(k) plan menus don’t include. Pre-tax contributions roll into a Traditional IRA; Roth contributions roll into a Roth IRA. The rollover should always be done institution-to-institution to avoid taxes and penalties. Every situation is different, so it’s worth reviewing your specific plan before making the move. What is wrong with leaving my 401(k) invested in an S&P 500 index fund in retirement? The S&P 500 yields just over 1% in dividends — not enough to cover most retirees’ living expenses. That means you’d need to sell shares regularly to generate cash. When the market is rising, that works. When the market is flat or declining, you’re forced to sell more shares to get the same dollar amount, which depletes your principal at the worst possible time. Over a 20- or 30-year retirement, that pattern can quietly cause serious damage to a portfolio. What is an income-focused retirement portfolio? An income-focused portfolio is built around investments that generate regular cash flow — primarily dividend-paying stocks in companies with long track records of consistent and growing dividends. The goal is for the income produced by the portfolio to cover living expenses, so you are not dependent on selling shares to fund retirement. Price appreciation is still part of the picture, but it’s the third priority, not the first. How many 401(k) accounts should I have going into retirement? Ideally, as few as possible. The average person approaching retirement holds three to five old 401(k) accounts from previous employers. Consolidating them into one or two IRAs — one Traditional, one Roth if applicable — simplifies beneficiary designations, required minimum distribution calculations, and overall portfolio management. It also makes it much harder to lose track of money you’ve worked decades to save. What is a safe withdrawal rate in retirement? A commonly referenced figure is 4% per year, which comes from historical research suggesting that withdrawal rate has a high probability of lasting 30 years across most market environments. However, the right withdrawal rate depends on your specific expenses, other income sources like Social Security or a pension, your tax situation, and how your portfolio is structured. An income-focused portfolio where dividends cover most expenses may allow for more flexibility than a pure growth portfolio using a fixed percentage rule. What does Dupree Financial Group do differently from a typical 401(k) plan? Dupree Financial Group is a fee-only, fiduciary RIA that manages separately managed accounts — meaning your investments are held in your name, not pooled into a fund. The firm builds income-focused portfolios around dividend-paying companies selected for their financial strength, cash flow, and dividend history. There are no products sold, no commissions, and no conflicts of interest. The focus is entirely on building a portfolio that generates reliable income and protects principal over a long retirement. 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 401(k) can actually support the retirement you’ve planned, 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 Your 401(k) Is Not a Retirement Plan appeared first on Dupree Financial.