The Tom Dupree Show

Bull Markets, Investor Hubris, and the Hidden Risks of Annuities Are you feeling smarter about your investments after years of strong market returns? In this episode of The Financial Hour of The Tom Dupree Show, Tom Dupree and Mike Johnson explore a critical truth that even legendary investors like Benjamin Graham learned the hard way: bull markets can create dangerous overconfidence. For those th...

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...

That is the trap. And it is compounded right now by something called recency bias — the tendency to assume that what has been happening will keep happening. Markets have gone up for a long time. New IPOs are capturing attention. There is enthusiasm in the air. And enthusiasm breeds complacency. People assume the funds that have been performing well will keep performing well, without checking wheth...

The Hidden Investment Risks Pre-Retirees and Retirees Don’t See Coming: Kentucky Retirement Planning Insights Are you approaching retirement and concerned about protecting your life savings from market volatility? In this comprehensive episode of the Tom Dupree Show, Kentucky retirement planning advisors Tom Dupree and Mike Johnson explore the multidimensional nature of investment risk and w...

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 t...

{ "@context": "https://schema.org", "@graph": [ { "@type": "PodcastEpisode", "name": "The Nike Cautionary Tale: What Happens When Leadership Loses Touch With Its Customers", "description": "Tom Dupree and analyst Michael Dawahare examine Nike's dramatic decline — from dominant global brand to a stock trading near 10-year lows — and draw clear parallels to retirement portfolio management.", "url":...

{ "@context": "https://schema.org", "@type": "PodcastEpisode", "name": "Buying a Stock Is Easy. Knowing When to Sell Is Everything.", "description": "Tom Dupree, Mike Johnson, and James Dupree walk through the complete sell discipline used at Dupree Financial Group — covering valuation signals, dividend yield compression, tax-smart exits, emotional traps, and real portfolio examples.", "url": "htt...

  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,...

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, a...

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...

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 we...

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 J...

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 su...

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 wha...

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...

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 illustrat...

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

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 di...

THE TOM DUPREE SHOW  |  PODCAST SHOW NOTES What Happens to Your Money When You’re Gone: A Practical Guide to Legacy Planning The Tom Dupree Show  |  Dupree Financial Group  |  dupreefinancial.com   |  859-233-0400 Air Date: April 25, 2026   Episode Description Most people spend decades building their wealth. Far fewer spend even an hour making sure it ends up where they intend. In this...

THE TOM DUPREE SHOW  |  PODCAST SHOW NOTES  A Practical Guide to Surviving the Financial Transition When Your Spouse Dies The Tom Dupree Show  |  Dupree Financial Group  |  dupreefinancial.com   |  859-233-0400 Episode Description Nobody wants to think about losing a spouse. But the financial consequences of that loss — the drop in Social Security income, the pension decisions that can never be un...

THE TOM DUPREE SHOW  |  PODCAST SHOW NOTES How Much Money Do I Need to Retire? The Income Answer That Actually Works The Tom Dupree Show  |  Dupree Financial Group  |  Evergreen Series  |  dupreefinancial.com   |  859-233-0400   Episode Description Ask Google how much you need to retire, and you will get a dozen different answers — a million dollars, two million, 25 times your expenses. Tom D...

The post Oil, Markets & Your Retirement | The Tom Dupree Show appeared first on Dupree Financial .

How Inflation Quietly Erodes Retirement Income — And What to Do About It Inflation is one of the most persistent and underestimated threats to a secure retirement. It doesn’t announce itself with a market crash. It doesn’t trigger news alerts. It just quietly shrinks what your dollars can buy — year after year, compounding on itself — until the retirement income you planned on no longe...

Managing your own investments can feel empowering — and for many people, it genuinely works well. But for those thinking about retirement or already living in it, DIY investing carries hidden risks that don’t always show up on your monthly statement. In a special Evergreen edition of  The Tom Dupree Show , host Tom Dupree and portfolio manager Mike Johnson break down what the  FINRA Investor...

The post HOUR3 3-28-26 appeared first on Dupree Financial .