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 thinking about retirement or already in retirement in Kentucky, this discussion reveals why understanding what you own—and maintaining investment humility—matters more than chasing the latest “simple solution.”

Unlike mass-market advisory firms that promote one-size-fits-all products, Dupree Financial Group emphasizes personalized investment management and portfolio transparency. This episode examines the psychology of market success, the realities of annuity contracts, and why direct access to portfolio managers who show you exactly what you own provides than opaque insurance products.

Mike Johnson shares a compelling historical example that resonates powerfully with today’s investment environment. Benjamin Graham—the father of value investing and Warren Buffett’s teacher—started his investment firm in the Roaring Twenties with $400,000. Within just three years, he turned that into $2.5 million.

As Mike explains: “Because of the great success over that short period of time, he knew that he knew it all, had Wall Street by the tail. He was thinking about owning a large yacht, a villa in Newport, race horses. And he said, ‘I was too young to realize that I’d caught a bad case of hubris.'”

The consequences? When Graham thought the worst of the 1930 market crash was over, he went all in—and even used leverage. The result nearly wiped him out personally, and his firm had to be bailed out by a partner. By 1932, his portfolio had lost over 50%, dropping from $2.5 million back to just $375,000.

Tom Dupree emphasizes the universal lesson: “The market can humble you real quick. You always have to view past successes in the lens of ‘okay, you may have had a good run, a good success, and some of that could be luck.'”

For those thinking about retirement who have benefited from recent market strength, this story serves as a critical reminder. Mike notes: “In the environment we’ve been in for the last several years in the market, some people have made life-changing money. Some people have made good returns and they got to their goal quicker than they thought they would.”

The question becomes: How do you respect the gift the market has given you? Through careful analysis with a local financial advisor who can provide personalized portfolio analysis rather than assuming past success will automatically continue.

Tom Dupree delivers a powerful critique of passive index investing that challenges conventional wisdom. When Mike mentions autopilot investing, Tom responds: “Autopilot isn’t ever autopilot. It’s a path that someone else has selected that you’re going on and you’re going on it because everybody else is.”

He continues with a critical observation: “In the case of an index, it’s an arbitrarily picked index of, say, 500 stocks that meet a certain size criteria, certain management criteria. What you don’t understand frequently is that by going on autopilot, you’re actually being told what to do. You’re not just going with the flow—there’s almost no thought going into it. There’s no real investing.”

Mike adds: “That’s the definition of mediocrity. Even if the return is good and everybody’s getting a good return because the market’s doing well, it’s still mediocrity because you’re not spending any time thinking about what you’re doing or how you’re doing it.”

Mike shares another psychological insight relevant to both inheritance and market windfalls: “We’ve seen it when someone inherits a windfall unexpectedly. A lot of times you see bad decisions with that money. Not all the time, but a lot of times. They’ve never had that kind of money before. They didn’t earn it. How can you respect it that way? How can you fear it?”

This applies directly to portfolios that have grown significantly without the owner fully understanding why or how. As Mike notes: “You don’t have the respect that also goes along with having made it. That’s why you see somebody that’s gradually built something over a long period of time—you don’t have that dopamine hit.”

For Kentucky retirement planning, this suggests the importance of understanding your investment philosophy and how each holding contributes to your goals, rather than simply celebrating portfolio growth without comprehension.

The second half of the episode tackles annuities—insurance products increasingly marketed to those in or approaching retirement. Mike presents sobering statistics: “In 2025, more Americans than ever are going to be turning 65—about 4.2 million US citizens will be turning 65 this year.”

He connects this demographic trend with research from Allianz: “64% of those surveyed were more worried about running out of money than death.” Tom responds: “That’s a really frightening comment on where a lot of people are.”

This fear creates demand for products marketed as “easy solutions”—but the reality is far more complex.

Mike breaks down the main annuity categories:

Index Annuities (Currently Most Popular): These promise you can earn up to a certain percentage annually without losing principal if markets decline. However, Mike explains the reality: “What you generally see is the rate of return on an index annuity averages pretty close to what the going CD rate is. That’s just the math of it.”

The problem lies in the fine print. Mike offers a detailed example: “Let’s say it’s a one-year point-to-point, and they say over the year you can make up to 6%. If you take that on a monthly basis, that’s half a percent a month. If in January the market goes up 1%, they credit you half a percent. But then come December, the market goes down 7%. It’s still up for the year, but December wiped out your credit. Even though the market is up for the year, you’re credited with zero.”

Immediate Annuities: The “purest form” where you give an insurance company principal in exchange for monthly income. Mike notes: “In those scenarios, you’re essentially getting your own money back for 15, 18 years, and then you start coming out ahead—not even taking into account time value of money.”

Fixed Annuities: Similar to CDs inside a tax-deferred wrapper. The primary risk? “The insurance company is able to use the money to earn a return, and in exchange for what they’re paying you. The risk that you’re agreeing to take on is inflation risk.”

Variable Annuities: Once popular in the 1990s and early 2000s but less common now due to previous issues at major insurers.

Beyond the obvious issues like surrender penalties (typically 7 years, but Mike has seen contracts as long as 14 years), several critical risks receive little attention:

Tom explains: “You have the insurance company as the counterparty, and the insurance company is investing its own money in corporate bonds, and some of those are going into these AI data centers.”

Mike expands on this: “Most people think when they have an annuity from an insurance company that it’s similar to something AAA because it’s insured. But what’s it insured by? It’s insured by securities that are backing it that could have trouble.”

Tom recalls historical examples: “I’ve seen it happen before. AIG, Executive Life before that—lots of it during my career. Hartford got in trouble with writing variable annuities.”

Mike reveals a current market concern: “There’s huge demand for bonds, and at the same time, the hyperscalers financing data centers are looking for buyers. The marginal buyer, the largest buyer, has been insurance companies of the data center debt.”

The consequence? “Spreads are the tightest they’ve been since the nineties. They’re being priced for perfection, priced almost like a Treasury. But we’re talking about bonds that are backed by a data center with a revenue stream that’s not yet to be determined.”

Tom summarizes: “When the spreads aren’t attractive, they’ll go out on the risk spectrum and take more risks to try to get a little more spread there. It’s a vicious cycle.”

Tom notes: “We didn’t even talk about the commission part of the annuity structure—the fact that it’s a very, very heavily commission-structured product.”

This contrasts sharply with Dupree Financial Group’s approach: “We are fee-based, and it takes all incentive to not—well, we’re fiduciaries also, so we must by law do what’s best for the client. That aligns our interest with the clients as well, which gives you a different product.”

Throughout the episode, Tom and Mike return to a core principle that distinguishes personalized investment management from packaged products. Tom explains: “Our style of investing is that when you get your statement, you are looking under the hood because it’s right there. You’re seeing what your money’s invested in. You’re not looking at an investment that’s invested your money in something else that you can’t see.”

Mike emphasizes why this matters over time: “You gain an understanding and a comfort level that’s not just taking somebody’s word for it. You’re seeing it with your own eyes over a long period of time. You see the income, you see price movement. You see these different aspects, and really, it makes the thing come to life.”

This transparency provides advantages that no annuity contract or index fund can match:

Tom adds: “We’ve always invested with people typically where we show them what is under the hood, what they own. It’s not a package product. It’s not an ETF, it’s not a mutual fund, it isn’t an annuity. It’s not some structured note. It’s bonds and stocks for the most part.”

Tom shares an honest perspective on how Dupree Financial Group has developed its approach: “There’s nothing like mistakes to help you with financial stuff. Mistakes are valuable if you can limit them to a certain amount to where it doesn’t knock you out of the box. But one of the best investing tools is making mistakes.”

He continues: “We’ve learned a lot in our firm with companies that we invested in that were just mistakes. We didn’t think they were mistakes at the time, but over time, you know, it was. And what we began to learn is: Don’t go there again. Let’s not do that one again.”

This experiential learning creates pattern recognition: “When you see something again, you see similarities and differences and you’re like, ‘Okay, that’s an opportunity.’ You just learn.”

This accumulated wisdom—built over 47 years in Tom’s case—represents a significant advantage of working with experienced local financial advisors rather than being assigned an investment counselor at a large national firm who may lack this depth of historical perspective.

Mike provides a framework for evaluating your current situation: “You have to pause and view it in the context of you, specifically your situation. There’s always going to be people richer than you. There’s always going to be people that have more of something than you have, and you have to be careful of viewing your situation through their context.”

He offers specific questions:

Mike emphasizes the market context: “This market—people who have had assets invested in the stock market for the last several years—you’ve been given a gift. Generally speaking, a gift in terms of the returns. And you need to respect the gift.”

How do you respect it? “By analyzing what it is that you have and thinking critically about how can this be used. Is it being utilized properly in terms of an investment mix, in terms of just an investment approach?”

A recurring theme throughout the episode is the danger of emotion-driven investing. Mike warns: “You have to be very concerned about allowing your investment decision to be driven only by fear. Yes. And to the point we were making in the first half, having a process—an investment process, an investment plan—that is dynamic enough to change when things need to change.”

He identifies two common fear patterns:

Fear of Loss: “Think about what fear drives you to do generally. You can look at fear in a situation like an annuity where you leave potential earnings on the table out of fear.”

Fear of Missing Out: “And then sometimes there’s fear of missing out in an up market and you can jump in when you shouldn’t.”

Tom adds: “Fear is a good thing to have in relation to investing.” Mike clarifies: “Respect. I would call it respect. A respect that things can happen.”

This balanced perspective—maintaining respect for market risks while following a thoughtful process—characterizes the approach at Dupree Financial Group. Review their market commentary archive to see how this philosophy has been applied across various market cycles.

Despite the episode’s critical examination of annuities, Tom shares an important caveat: “I have seen annuities where they actually make sense for the person. And in those instances, keep it.”

He shares a specific example: “I had a client one time that did buy an annuity. It grew in value. He passed away and his wife received a significantly higher payout than what would have happened if we had just invested in investments because the market had gone down, but the value of the annuity had gone up.”

Tom reflects on the outcome: “That was a case where I feel like that lady was blessed. I’ve seen it happen too where there have been clients that I feel like—and the only way I can put it is—it’s like God touched them in ways that I can’t explain. Just in ways that it’s just a blessing.”

The key takeaway? “You need to have an unbiased analysis of the contract. What are the terms? Does it actually accomplish your goals?”

If you currently own an annuity, Mike encourages: “You can give us a call and we can talk with you about the specifics of your contract.”

Mike concludes with a fundamental truth about retirement investing: “Investing’s never just a simple one decision solution. It’s a process. It has to be because things change. Markets change, people’s lives change, and there has to be a process behind what you’re doing.”

Tom reinforces the warning: “Whenever they tell you you don’t have to look under the hood with this investment, you better look under the hood.”

This principle applies equally to:

For those thinking about retirement or already in retirement in Kentucky, the alternative is working with advisors who provide direct access to portfolio managers, show you exactly what you own, and maintain a process-driven approach that adapts to changing circumstances while remaining grounded in time-tested principles.

If you’re concerned that recent market success may have created blind spots in your retirement planning—or if you’re evaluating whether an annuity truly serves your interests—Dupree Financial Group offers complimentary portfolio reviews for Kentucky residents thinking about retirement or already in retirement.

During your consultation, you’ll receive:

Don’t let bull market confidence create blind spots in your retirement plan. Schedule your complimentary portfolio review today.

Call Dupree Financial Group at (859) 233-0400 or visit www.dupreefinancial.com to schedule directly from our homepage.

Experience the difference that personalized investment management, portfolio transparency, and direct access to portfolio managers makes in your Kentucky retirement planning journey.

This phrase captures how extended periods of market gains can create false confidence in investment abilities. As the Benjamin Graham story illustrates, even legendary investors can mistake favorable market conditions for personal genius. For those in or approaching retirement in Kentucky, this means strong recent returns shouldn’t lead to overconfidence or excessive risk-taking. Working with a local financial advisor who provides objective perspective helps distinguish between skill and fortunate timing.

After turning $400,000 into $2.5 million in just three years during the 1920s, Graham developed what he called “hubris”—thinking he “had Wall Street by the tail.” When he believed the 1930 crash was over, he went all in using leverage. The market continued falling, and his portfolio dropped back to just $375,000. The lesson: even brilliant investors can be humbled by markets when success breeds overconfidence. His partner had to bail out the firm, and Graham didn’t take a salary for years while making clients whole.

While index funds work for some investors, Tom Dupree notes they represent “a path that someone else has selected that you’re going on because everybody else is.” There’s “no real investing” happening—just following an arbitrary selection of stocks based on size criteria. Mike Johnson adds this is “the definition of mediocrity” because “you’re not spending any time thinking about what you’re doing.” For Kentucky retirement planning, personalized investment management provides understanding of actual holdings rather than passive acceptance of whatever an index contains.

Index annuities promise upside participation (often “up to 6% annually”) with downside protection. However, the mechanics rarely deliver. In a typical point-to-point structure, if the market gains 1% monthly for 11 months (crediting you 0.5% monthly due to caps), you’d have 5.5% credited. But if December sees a 7% decline, your entire credit gets wiped out even though the market is up for the year. The result: returns typically match CD rates despite the complex structure. The fine print and monthly/quarterly calculations favor the insurance company.

Counterparty risk refers to the possibility that the insurance company backing your annuity could face financial trouble. Insurance companies invest your principal in corporate bonds and other securities to earn returns higher than what they promise to pay you. Currently, many insurers are heavily invested in AI data center debt with unproven revenue streams. Historical examples like AIG, Executive Life, and Hartford show this isn’t theoretical—insurance companies can and do get into trouble, potentially affecting annuity values.

Yes, though they’re rare. Tom Dupree shares an example where a client’s widow received significantly more from an annuity than she would have from traditional investments because her husband passed away after the annuity grew but when markets had declined. However, these favorable outcomes are exceptions. The key is having an unbiased analysis of your specific contract terms and whether they truly accomplish your goals. If you own an annuity, Dupree Financial Group can review whether keeping it makes sense for your situation.

Looking under the hood means seeing exactly what individual stocks and bonds you own rather than just seeing a packaged product name and account value. Tom Dupree explains: “When you get your statement, you are looking under the hood because it’s right there. You’re seeing what your money’s invested in, not what packaged product your money is in.” This transparency allows you to understand what companies you own, why you own them, and how they generate income—creating genuine comfort during market volatility.

Autopilot investing—whether through target-date funds, robo-advisors, or simple index strategies—means following a prescribed path with little thought given to your specific situation. Tom notes you’re “actually being told what to do” rather than having a strategy tailored to your goals, timeline, and risk tolerance. As retirement nears, one-size-fits-all approaches can leave you overexposed to market declines or invested in ways that don’t generate needed income. Personalized investment management adapts to your changing life circumstances.

Mike Johnson advises: “You’ve been given a gift. Generally speaking, a gift in terms of the returns. And you need to respect the gift.” Respecting it means analyzing what you have, ensuring your investment mix still makes sense, and not assuming past success will automatically continue. Ask: “Do the numbers work for you at where they are?” and “Is there an investment plan, or has it just been on autopilot?” A complimentary portfolio review with Kentucky retirement planning specialists can provide this objective assessment.

Fear-driven investing shows up in two ways: fear of loss (leading to overly conservative choices like annuities that sacrifice potential growth) and fear of missing out (jumping into hot investments at precisely the wrong time). Both create poor outcomes. The alternative is what Tom calls “respect” for markets—acknowledging risks while following a thoughtful process. Mike emphasizes having “an investment plan that is dynamic enough to change when things need to change” rather than reacting emotionally to short-term events.

Annuities typically involve substantial commissions paid to the salesperson, creating incentives that may not align with your interests. Tom Dupree explains: “We are fee-based, and it takes all incentive to not—well, we’re fiduciaries also, so we must by law do what’s best for the client. That aligns our interest with the clients.” Fee-based structures mean advisors earn based on portfolio performance and client retention, not product sales. This fundamental difference affects which solutions get recommended.

The Financial Hour provides practical investment wisdom and retirement planning guidance for Kentucky residents approaching or living in retirement. Hosted by Tom Dupree, founder of Dupree Financial Group, with insights from portfolio manager Mike Johnson, each episode delivers actionable strategies based on decades of experience in personalized investment management and portfolio transparency.

Listen to more episodes and read additional market commentary at www.dupreefinancial.com/podcast.

The post Bull Markets, Investor Hubris, and the Hidden Risks of Annuities  appeared first on Dupree Financial.

When the tech-heavy Nasdaq drops 4% in a week and market sentiment shifts dramatically, how should those thinking about retirement or already in retirement respond? In this timely market update from The Financial Hour of The Tom Dupree Show, Tom Dupree and Mike Johnson provide real-time insights into recent market turbulence while reinforcing a critical principle: predictable income trumps price speculation when you’re living off your portfolio.

Unlike mass-market advisory firms that leave clients guessing about portfolio holdings during volatile periods, Dupree Financial Group’s personalized investment management approach ensures you understand exactly what you own and why. This episode demonstrates how direct access to portfolio managers who invest in individual securities—rather than opaque packaged products—provides clarity and confidence when markets get choppy.

Tom Dupree opens the episode with characteristic directness about Thursday’s market action: “Stocks notch worst day in over a month as tech sell-off intensifies. The market was down 794, which you know, was probably about right and I think it’s still going down today.”

But rather than expressing alarm, Tom’s reaction is measured: “I mean, you had to have known it was gonna happen.”

Mike Johnson provides context: “Last Friday, you had a huge downdraft early Friday morning, and then it turned around, came back. That is a sign of a toppy market. At some point, you’ll get a longer sell-off.”

Tom explains the mechanics behind the sell-off: “When you have things trading at stretch multiples, you don’t necessarily have to have bad news for those things to come back down to earth. Sometimes just the news—they run up on the news or the expectation of the news, then they come off on the news itself.”

This phenomenon particularly affects high-growth technology stocks that trade at premium valuations. Mike notes: “Since last Monday, the Nasdaq is down about 4%. That’s the super speculative, more growthy kind of names.”

For those thinking about retirement in Kentucky, this volatility underscores why personalized portfolio analysis focused on income production rather than speculation provides more sustainable results.

One of the week’s most significant developments involved a dramatic shift in Federal Reserve rate cut expectations. Mike explains: “The market has drastically changed its expectations in terms of a Fed rate cut in December. It was priced in like 95% chance that they were gonna cut rates in December. Today, that’s basically a coin flip—50/50 is where it’s pricing it in.”

Why does this matter for stock valuations? Mike provides the technical explanation: “Growth stocks will typically warrant a higher multiple when rates are low or going down, positively correlated to falling interest rates. Warren Buffett used to talk about it—it’s the risk-free rate of return, typically the US government bond.”

Tom adds practical context: “If it is lower, then it allows for a growth stock’s P/E to go higher. It doesn’t always correlate directly, but at times, there is a positive correlation that way. It’s a tailwind—it allows for the speculation, gives it permission to go higher.”

However, both emphasize this is “not at all necessarily related to their business or how well it’s doing.” A company can report strong earnings and still see its stock drop 30% if market expectations were even higher.

This disconnect between business fundamentals and stock price movements highlights why the Dupree Financial Group investment philosophy prioritizes income-producing securities over growth speculation for retirement portfolios.

Tom shares a striking performance contrast: “Our firm, the portfolio we manage, is a more conservative setup. We’ve actually made a little money in here. Doesn’t mean we’ll always do that, but if you want to invest in the growth of America over a long period of time, you should have some money in growth stocks.”

He explains their balanced approach: “We’re beginning to buy some around the margins. Not doing too well at it the last couple of days, but it’s tiny smidgen amounts. But we will do well with it because I think our research is good that we’re doing.”

The portfolio’s resilience comes from its core structure. Tom details: “For the other mix, we are buying dividend-paying stocks that are well known and government bonds. And so it’s enabled us to put together a pretty good year so far. We’re a month and a half from being over with.”

This approach demonstrates a fundamental principle for those in or approaching retirement: predictable income from dividends and bonds provides stability that growth speculation cannot match.

Mike reinforces this: “You made a lot of money, especially since April, in these growthier names. But they all finally give up the ghost at some point.”

Mike identifies an important trend: “The last two weeks, you have started to see the—if you want to call it—flight to quality. You started to see areas broaden out into the rally, broaden out into other areas. Healthcare has actually done pretty well.”

Tom shares a specific investment decision that illustrates their active management approach: “We sold our Berkshire at a very nice price, and it pulled way back. And now we’re back in. We weren’t market timing—we were simply looking at the valuation and based on where investors seemed to think the company was gonna go, given that the big dude was just retiring. We thought it was too expensive. Sold it, bought it back. Looks like they’re still executing.”

Mike adds context: “He actually just put out his Thanksgiving letter. It was five, six pages. He kind of does his little stories in there growing up. It was a nice letter. I’d encourage listeners to go read it.”

The letter mentions Greg Abel (Buffett’s successor), gives a shout-out to Charlie Munger, and confirms Buffett will continue writing Thanksgiving letters, though stepping back from shareholder letters and annual meeting speaking.

Tom notes why Berkshire attracts capital during volatile periods: “You saw a flight to quality because they have just an enormous cash hoard right now, and plus the businesses that they own—those are rock solid good companies.”

This selective buying and selling based on valuation—rather than following index allocations—exemplifies the advantages of personalized investment management over autopilot strategies.

Mike highlights a trend emerging from the AI and technology revolution: “You’ve seen several companies announce large job layoffs this week. Verizon announced 15,000 cut to the workforce, but when you look at it as an investor, this is the aspect of AI and just technology that we’ve been talking about the last year.”

He explains the market’s reaction: “As the technology matures, you’re gonna see companies benefit from just the economies of scale. Verizon, ‘s stock was green, partly because of that announcement. They also appointed a new CEO who’s gonna focus more on the customer.”

Tom adds historical perspective: “Anytime there’s a technological revolution, there’s a retraining process.”

For Kentucky retirement planning, this underscores the importance of owning quality companies that can adapt to technological change while continuing to generate income—the type of holdings you can actually see and understand when working with local financial advisors who provide portfolio transparency.

Mike provides timely information for retirement savers: “They just came out with the new contribution limits for 401(k)s and IRAs for 2026.”

Mike highlights a critical change: “If you have a 401(k) with your employer and you’re—as the IRS quantifies it—a high earner (which in their definition is if you make over $150,000), if you do a 401(k) catch-up to your plan, which that’s if you’re over 50, they changed the rule on this. That catch-up contribution now has to go to a Roth 401(k).”

He acknowledges the complexity: “It gets a little complicated because of if it’s this, then it’s that and the little rules. If you have questions about your 401(k), give us a call. We can talk with you about it because the rules are important. You want to maximize the assets that you have and you want to use everything to your advantage that’s given to you.”

Tom delivers a contrarian perspective on retirement planning’s most popular vehicle: “Money that you can save aside that’s not in a 401(k)—that is actually your own money. You can invest that money far more creatively than you can within most 401(k) plans.”

He continues: “I would actually advise people not to use their 401(k) as their sole retirement planning source. Invest in some things outside of that that you can—buy some stocks. You can’t buy stocks inside a 401(k). I’m glad to have 401(k) rollovers when they come to us. I think it’s great. I’m glad that people have built money over time, but it’s not the most creative way to invest.”

Mike offers a solution many don’t know exists: “Let’s say you’re still working and you’re 59 and a half. The employer matches—you can still take part in the employer match into the 401(k), but you can take your balance of the 401(k), move that to an IRA. It’s what’s called an in-service rollover. No tax consequences.”

The advantage? “Then you can invest it in some of these other things that we’ve been talking about. You can do that while at the same time still utilizing the 401(k) for the match or the tax deferral. It’s just strategically using the tools that are available.”

This flexibility allows those approaching retirement to maintain employer matching benefits while gaining access to individual stock and bond investing—the foundation of Dupree Financial Group’s income-focused approach.

Tom references the statistic Mike shared in a previous episode: “You were talking about earlier—there was a study done that Americans are more worried about running out of money than they are about death.”

He connects this to retirement timing: “I would think that applies more to people who’ve already retired who know that they’re not doing anything more to put anything back. That’s why I tell people, if you don’t have to, don’t retire because it’s not good for you. It’s good for people to have something to do, a reason to get out of bed in the morning, a reason to do this, to do that.”

Mike emphasizes a critical distinction: “The biggest success stories of clients have been people who have that—what are you retiring to? It’s not where you’re retiring from. What are you retiring to? That’s where we’ve always seen success—is when they’re engaged, they’re active. And a lot of times, more and more often, it’s some sort of gainful employment.”

Tom agrees: “Gainful employment can be a lot of things, but it has to be something that requires you to be involved in something—putting some points on the board.”

For Kentucky retirement planning, this philosophical perspective complements the financial strategy: combining meaningful activity with income-producing investments creates both purpose and security.

Mike delivers a candid assessment: “The idea of retirement—I don’t care how big the pool of assets are—the idea of retirement is a risky proposition just because it’s unnerving. It’s scary. It’s a scary thing for people for a reason because you’re giving up control. You’re trying to replicate an income stream through the assets that you’ve saved. So it is a risky thing just by nature, and people are living longer.”

He defines the advisor’s role: “Our job as advisors to our clients, as investors, is how do we in the most prudent way produce an income stream?”

Tom responds: “Well, that’s where the rubber meets the road—cash flow. And to do that takes experience. You have to have seen some things in the past that worked and some things that didn’t work.”

This accumulated wisdom—47 years in Tom’s case—represents a significant advantage of working with experienced local financial advisors rather than being assigned an investment counselor at a large national firm who may lack this historical perspective and market cycle experience.

Tom shifts to the practical implications of recent market choppiness: “Right now, you’re gonna need to look at some of these stocks that have gotten beat up and find some bargains in there because they’re gonna be there. There’s always opportunities.”

He recalls recent successful positioning: “In April, when everybody was scared to death, you’re starting to see some things now that we’ve added several things to the portfolio in the last three weeks.”

When asked to name something recognizable they’ve added, Tom reveals: “One place where you buy your milk and your gasoline—Kroger. We bought some Kroger.”

This purchase exemplifies several principles:

This active decision-making—buying specific companies for specific reasons at specific times—contrasts sharply with passive index investing that automatically buys whatever the index holds, regardless of valuation or business quality.

Review the market commentary archive to see how Dupree Financial Group has identified opportunities across various market environments.

Mike emphasizes the foundation of their approach: “Markets are choppy—that’ll probably continue. That’s the nature of markets. But just you have to be diligent, always looking for opportunities, always looking for things that accomplish your goals. Fundamentals—look at the companies. That’s what we’re doing. We try to do that every day. We try to find things that work for our clients. That’s the goal.”

He highlights what makes this possible: “But there’s accountability. Our clients know what they own. And the cornerstone of the portfolio is income because that is more predictable than price appreciation or price movement.”

Tom connects this to retirement reality: “It’s very important in retirement too because you’ve got to have income to pay the bills that you’re used to having your work income pay for.”

This focus on predictable cash flow rather than unpredictable price appreciation represents the fundamental difference between speculation and sustainable retirement investing.

Throughout the episode, the theme of transparency and accountability recurs. When clients can see exactly which companies they own—Kroger, Berkshire Hathaway, dividend-paying stocks, government bonds—they understand where their retirement income originates.

This contrasts with:

The advantage of transparency becomes especially clear during volatile markets like the current environment. When the Nasdaq drops 4% but your portfolio generates positive returns, you understand why: you own dividend-producing companies and government bonds selected for income stability, not speculation on growth.

Tom provides his near-term perspective: “You’re gonna have your up days and down days. And you’re gonna make your most money with growth over time. Take some risk, think about what you’re buying, and go for it.”

Mike offers guidance for the coming period: “Markets have been choppy the last couple of weeks. That’ll probably continue. That’s the nature of markets.”

The takeaway for those thinking about retirement or already in retirement in Kentucky: choppy markets are normal, but having experienced advisors who actively manage portfolios—buying quality companies when they’re on sale, maintaining income-producing core holdings, and providing direct access to explain every decision—makes navigating volatility far less stressful than watching index funds fluctuate with no understanding of what you actually own.

If recent market turbulence has you questioning whether your portfolio is positioned correctly for retirement—or if you’re realizing you don’t actually know what you own or why you own it—Dupree Financial Group offers complimentary portfolio reviews for Kentucky residents thinking about retirement or already in retirement.

During your consultation, you’ll receive:

Don’t let market volatility create anxiety about retirement. Schedule your complimentary portfolio review today.

Call Dupree Financial Group at (859) 233-0400 or visit www.dupreefinancial.com to schedule directly from our homepage.

Experience the difference that personalized investment management, income-focused strategies, and direct access to portfolio managers makes when markets get choppy.

The Nasdaq dropped approximately 4% as growth stocks trading at “stretch multiples” (high valuations) pulled back. Tom Dupree explains this was predictable in a “toppy market” where stocks had run up significantly. The catalyst included shifting Federal Reserve rate cut expectations (from 95% probability to 50/50 for December) and natural profit-taking after strong gains. Importantly, this correction didn’t require bad news—simply the reality meeting elevated expectations.

While the Nasdaq fell 4%, Tom Dupree reports their more conservative portfolio “actually made a little money” during the same period. The portfolio’s foundation of dividend-paying stocks and government bonds provided stability while they selectively added growth positions “around the margins” in small amounts. This demonstrates how income-focused investing protects capital during volatility while still participating in growth opportunities.

Mike Johnson explains that growth stocks typically warrant higher price-to-earnings multiples when interest rates are falling. Warren Buffett discussed this concept: the risk-free rate (typically US government bonds) serves as a baseline for all investments. When this rate is lower, investors will pay more for growth potential. Tom adds it’s “a tailwind that allows for speculation” and “gives it permission to go higher.” However, this is separate from actual business performance—a company can report great earnings and still fall if rate expectations shift.

Mike describes how, during market uncertainty, investors move capital toward more stable, proven companies and assets. Recent examples include increased interest in healthcare stocks, Berkshire Hathaway (with its enormous cash reserves and solid businesses), and dividend-paying stocks. This contrasts with speculative growth investments. For those in Kentucky retirement planning, this trend validates the income-focused approach that prioritizes quality over speculation.

The IRS announced: 401(k) contributions increase to $24,500 (up $1,000); IRA contributions increase to $7,500; and individuals aged 60-63 can contribute even more. A significant new rule: high earners (defined as making over $150,000) must now make catch-up contributions (for those over 50) to a Roth 401(k) rather than traditional pre-tax. Mike recommends calling for personalized guidance since “it gets a little complicated” with various age brackets and income thresholds.

Yes, through an “in-service rollover” if you’re 59½ or older. Mike explains you can continue receiving employer matching in your 401(k) while simultaneously moving your existing balance to an IRA with no tax consequences. This allows investment in individual stocks and bonds—which Tom notes “you can’t buy stocks inside a 401(k)”—while maintaining employer benefits. This strategy provides far more investment flexibility than typical 401(k) options like index funds or target-date funds.

Tom Dupree advises against this: “I would actually advise people not to use their 401(k) as their sole retirement planning source.” He notes that money outside a 401(k) “is actually your own money” that “you can invest far more creatively.” While he’s “glad to have 401(k) rollovers,” he acknowledges “it’s not the most creative way to invest” since most people invest through indexes or target-date funds—”zero in terms of creativity.” Maintaining savings in both qualified and non-qualified accounts provides more flexibility.

Mike emphasizes: “The cornerstone of the portfolio is income because that is more predictable than price appreciation or price movement.” Tom adds it’s “very important in retirement too because you’ve got to have income to pay the bills that you’re used to having your work income pay for.” When living off your portfolio, you can’t wait for prices to recover from a downturn—you need cash flow regardless of market conditions. Dividends and bond interest provide this predictability that growth speculation cannot.

Mike explains: “I don’t care how big the pool of assets are—the idea of retirement is a risky proposition just because it’s unnerving. It’s scary. You’re giving up control. You’re trying to replicate an income stream through the assets that you’ve saved.” People are also living longer, extending the period assets must last. The solution, according to Tom, requires experience: “To do that takes experience. You have to have seen some things in the past that worked and some things that didn’t work.”

Tom offers contrarian advice: “If you don’t have to, don’t retire because it’s not good for you. It’s good for people to have something to do, a reason to get out of bed in the morning.” Mike emphasizes the critical question: “What are you retiring to? It’s not where you’re retiring from. It’s what are you retiring to?” Their most successful clients remain engaged and active, often with “some sort of gainful employment.” This philosophy combines financial security with life purpose—both essential for successful retirement.

Tom advises: “You’re gonna need to look at some of these stocks that have gotten beaten up and find some bargains in there because they’re gonna be there. There are always opportunities.” He recalls April when “everybody was scared to death” and notes they’ve “added several things to the portfolio in the last three weeks”—including Kroger. The key is having a process: “Be diligent, always looking for opportunities, always looking for things that accomplish your goals. Fundamentals—look at the companies.” This requires direct access to portfolio managers who actively manage rather than autopilot index strategies.

Mike states, “Our clients know what they own. And the cornerstone of the portfolio is income.” When markets drop and the Nasdaq falls 4%, but your portfolio generates positive returns, transparency lets you understand why: you own dividend-producing companies selected for income stability, not speculation. This contrasts with index funds (where you own arbitrary collections of stocks), target-date funds, or annuities, where you never see underlying holdings. Understanding what you own eliminates anxiety during volatility.

The Financial Hour provides real-time market insights and practical retirement planning guidance for Kentucky residents approaching or living in retirement. Hosted by Tom Dupree (with 47 years of investment experience), founder of Dupree Financial Group, with portfolio manager Mike Johnson, each episode delivers actionable strategies based on decades of navigating market volatility through income-focused, transparent investment management.

Listen to more episodes and read additional market commentary at www.dupreefinancial.com/podcast.

The post Why Income-Focused Investing Beats Speculation for Kentucky Retirement 11-15-25 appeared first on Dupree Financial.

Markets are at record highs again. If you’ve been diligently dollar-cost averaging into your 401(k) for years, watching your portfolio grow, you might be feeling pretty good right now. But here’s a critical question: Have you adjusted your risk management to match where you are in life today?

At Dupree Financial Group, we recently revisited some key concepts from Morgan Housel’s excellent book, The Psychology of Money. These principles are especially relevant in today’s market environment, and they might change how you think about your investment strategy.

Housel makes a fascinating observation: “Getting money requires taking risks, being optimistic, and putting yourself out there. But keeping money requires the opposite of taking risk. It requires humility and fear that what you’ve made can be taken away from you just as fast.”

For years, you’ve been an optimist—investing in your 401(k), believing in human ingenuity and the ability of companies to create value. That optimism has likely served you well. But as your portfolio has grown and you’ve moved closer to retirement, have you adjusted your approach?

The risk you were taking at 35 shouldn’t be the same risk you’re taking at 60. Yet many investors continue with the same aggressive allocations simply because “it’s been working.” That’s not a strategy—that’s momentum, and momentum eventually stops.

One of the most powerful concepts in Housel’s book is the idea of “enough.” This isn’t about being conservative or afraid to grow your wealth. It’s about clearly understanding what happens if things go wrong.

If you make this investment and it doesn’t work out, will it derail your retirement goals? That’s the question that matters.

Having “enough” means you can identify a baseline—a number that allows you to accomplish your goals. Once you have that baseline, you can make informed decisions about risk. You can look at your portfolio and ask: “Do these numbers work for me now, where they are today?”

With markets at current valuations and some investors heavily concentrated in high-flying tech stocks, this question has never been more important. Yes, you might have been rewarded for that concentration. But is the additional risk still worth it if you already have enough to meet your goals?

According to Housel, there are some things that should never be risked, no matter the potential gain:

Reputation – In our business, reputation is everything. It’s all we have, and it’s all we’ll ever have. We learned this lesson early when an energy partnership we recommended didn’t work out as planned. Even though legally we weren’t obligated to make clients whole, we did—because our reputation was worth more than the potential loss.

Happiness and Peace of Mind – True wealth isn’t just about a number on a statement. It’s about having the freedom to make choices, to sleep well at night, and to do what’s right when the opportunity presents itself. We’ve seen clients with substantial portfolios who aren’t happy because they’re constantly worried about market volatility. And we’ve seen clients with more modest portfolios who sleep soundly because their investments align with their goals and values.

Freedom and Independence – The real value of wealth isn’t in consumption—it’s in the flexibility it provides. The ability to choose what you do with your time, to help family members in need, to support causes you care about—that’s what financial independence really means.

Here’s something most financial advisors won’t tell you: life isn’t a spreadsheet.

From a purely mathematical standpoint, it might not make sense to pay off a 3.5% mortgage when you could potentially earn more in the market. But if paying off that mortgage helps you sleep better at night and aligns with your values, then it’s the right decision for you.

We call this being “reasonable” rather than purely “rational.” Reasonable takes into account your feelings, your values, and what makes sense for your life—not just what looks best on paper.

This principle applies to investment strategy too. Right now, many investors are actively trading stocks, caught up in the AI and tech frenzy. They’re buying this stock, selling that one, assuming they can beat the market over the long term.

Here’s a sobering statistic: Over the last 15 years, 96% of large-cap growth mutual funds have underperformed their benchmark index. These are funds managed by teams of professional researchers with access to resources that individual investors can’t match. If they’re struggling to beat the index, what are the realistic odds for individual stock pickers?

This doesn’t mean individual stock ownership is wrong—far from it. But the strategy needs to be reasonable and sustainable. At Dupree Financial Group, we focus on generating income streams through dividends and interest from quality companies. Our clients understand what they own and why they own it. When markets get volatile—and they always do eventually—this familiarity and understanding helps them stay the course.

Because here’s the truth: compounding only works if you give it time. And you can only give it time if you don’t panic and sell at the worst possible moment.

Here’s a final insight that might change how you think about money: wealth is invisible.

When you see someone driving a $100,000 car, the only thing you know for certain is that they’re either $100,000 poorer than they were before or they’ve taken on debt. That’s it. That’s all that purchase tells you.

Being rich is about consumption—it’s what you can see. But wealth is what’s building up behind the scenes, hidden from view. Wealth is the gap between what you earn and what you spend, compounded over time.

Think of it like exercise. One study found that people overestimate the calories they burn during a workout by a factor of four. They think, “I worked out, I deserve a reward,” and end up consuming more calories than they burned. The net result? Weight gain, not loss.

Wealth building works the same way. You might have money coming in from various sources, but if your spending increases proportionally (or worse, exceeds your income), you’re not actually building wealth—you’re just funding a lifestyle.

After 47 years in the investment business, here’s what we know: The key isn’t timing the market. It’s understanding what you own and why you own it.

It’s about switching from an income-making role to an income-producing role—making your money work for you rather than constantly working for your money.

Markets don’t always go up. They go sideways, they go down, and yes, sometimes they go up dramatically. But when you have regular income needs—monthly withdrawals, required minimum distributions, or simply the need to fund your lifestyle—you can’t rely on the unpredictability of market growth alone.

This is why we focus on dividends and interest income. It’s more predictable, more consistent, and it allows your principal to keep working for you even when markets are volatile.

If there’s one takeaway from all of this, it’s this: If you don’t know what you own in your portfolio, you need to.

With markets at current valuations, with the dramatic concentration in certain sectors, with interest rates and economic conditions in flux, now is the time to take an honest look at your portfolio and ask:

These aren’t easy questions, but they’re essential ones. And you don’t have to answer them alone.

At Dupree Financial Group, we’ve spent decades learning from our clients—seeing what real wealth building looks like, understanding the mistakes to avoid and the strategies that work. We’re here to help you make sense of your portfolio and create a plan that aligns with your goals and values.

Making money requires taking risks, being optimistic, and actively pursuing opportunities. Keeping money requires a different mindset—one focused on humility, risk management, and understanding that what you’ve built can be lost just as quickly as it was gained. As you approach retirement, your investment strategy should shift from aggressive growth to protecting what you’ve accumulated while still generating income.

“Enough” is the amount you need to accomplish your specific goals without taking unnecessary risks. To determine this number, work with a financial advisor to calculate your expected expenses, desired lifestyle, healthcare costs, and legacy goals. Once you know your baseline “enough” number, you can make informed decisions about whether additional risk in your portfolio is truly necessary or just greedy.

From a purely mathematical standpoint, it may not always make sense to pay off a low-interest mortgage when you could potentially earn more in the market. However, many retirees find tremendous peace of mind in entering retirement debt-free. This is a perfect example of choosing what’s “reasonable” for your situation over what’s purely “rational” on paper. The right answer depends on your interest rate, tax situation, risk tolerance, and personal values.

Over the last 15 years, only 4% of large-cap growth mutual funds have outperformed their benchmark index. This means 96% of professionally managed funds with teams of researchers underperformed a simple index. This statistic highlights why individual stock picking is so challenging and why having a clear, sustainable investment strategy focused on quality companies and income generation often makes more sense for retirement investors.

As you near retirement, your focus should shift from pure growth to income generation and capital preservation. This doesn’t mean abandoning stocks entirely, but it does mean reassessing your risk exposure and ensuring your portfolio can generate the income you’ll need without forcing you to sell assets during market downturns. A dividend and interest-based strategy can provide more predictable cash flow than relying solely on capital appreciation.

Being rich is about consumption—the visible signs of spending like expensive cars, homes, and vacations. Wealth, on the other hand, is what you don’t see. It’s the gap between what you earn and what you spend, compounded over time. Wealthy individuals focus on building assets that generate income and provide freedom, rather than funding a lifestyle that requires constant work to maintain.

Dividends provide predictable, consistent income regardless of market volatility. When you need to withdraw money from your portfolio during retirement, relying solely on stock price appreciation means you might be forced to sell during a downturn, locking in losses. Dividend-paying quality companies provide cash flow that doesn’t require selling shares, allowing your principal to remain invested and continue compounding over time.

At minimum, you should conduct a comprehensive portfolio review annually. However, major life changes—approaching retirement, receiving an inheritance, selling a business, or significant market movements—warrant immediate reviews. The key is ensuring your portfolio allocation still matches your current life stage, risk tolerance, and goals, not just continuing with the same strategy because it worked in the past.

Look for an advisor who takes time to understand your complete financial picture, not just your investment accounts. They should be able to explain what you own and why you own it in clear terms. Ask about their investment philosophy, how they’re compensated, and whether they have experience working with clients in your specific situation. Most importantly, find someone who values protecting your wealth as much as growing it.

Ready to take a closer look at your portfolio? Call us at 859-233-0400 or schedule a complimentary portfolio review directly on our website at dupreefinancial.com.

Dupree Financial Group – Where we make your money work for you.

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This week brought a stark reminder that what goes up doesn’t always continue in a straight line. The major indices experienced significant selling pressure, with the NASDAQ leading the decline. While some investors may be surprised by this volatility, it’s exactly the kind of environment we’ve been preparing for at Dupree Financial Group.

In this episode of The Financial Hour, Tom Dupree and Mike Johnson discuss the recent market selloff, why elevated valuations have been a flashing warning sign, and, most importantly, why our strategic bond positioning is designed to protect and create opportunities for our clients.

The selloff began Tuesday with the NASDAQ down approximately 2%, while the S&P 500 fell 1.2%. Thursday brought another 1% decline in the S&P, and Friday continued the downward pressure with the S&P down about 1.1% and the NASDAQ falling another 1.5%.

While some media attention focused on Michael Burry announcing short positions, the real story is much simpler and more fundamental: valuations have been stretched for quite some time.

“We’ve been hollering it from the rooftop for a while now. The market eventually realizes that maybe these things aren’t gonna grow 20% in perpetuity forever.” – Tom Dupree

In recent meetings with companies building data centers and manufacturing components for AI infrastructure, the conversation has taken on a familiar tone. These are excellent companies with impressive technology, but the projections for future demand sound almost too good to be true.

“The amount of demand that they talk about having out into the future—classic top sounding stuff. It just sounds way too good to be true. And the valuations of these companies are as if this whole thing they’re talking about happening has already taken place.” – Tom Dupree

The challenge isn’t whether data centers are important or whether AI will continue to grow. The challenge is that current stock prices already reflect perfection, leaving little room for anything less than extraordinary outcomes.

Current market valuations tell a concerning story:

To put that last number in perspective, at the peak of the tech bubble, the CAPE ratio reached about 44-45. We’re now at valuation levels similar to where the market stood in 1999.

“The level we are now is about where the market was from a valuation standpoint in 1999.” – Mike Johnson

While valuations don’t provide precise timing for market corrections, they absolutely serve as warning signals that should influence how you position your portfolio—especially if you’re in or approaching retirement.

Looking at past market melt-ups that preceded significant declines reveals striking similarities:

The pattern is clear and concerning. While this doesn’t guarantee an immediate crash, it does underscore why defensive positioning makes sense for retirement portfolios.

For the past several months, Dupree Financial Group has been systematically taking profits from positions that performed well and reallocating into treasuries and money market funds. This isn’t market timing—it’s valuation-based tactical positioning.

Our strategic bond purchases serve three critical purposes:

If economic conditions slow and interest rates decline, bond prices rise. This means the bonds we’re purchasing now could generate capital gains in addition to their yield.

Current treasury yields around 4% look increasingly attractive, especially if interest rates fall in the future. When short-term money market rates potentially drop to 2%, our clients will still be earning 4% from their bond holdings.

Bonds provide liquidity that can be converted into stocks if valuations become truly attractive. Think of them as “dry powder” waiting for the next major buying opportunity.

“It’s a source of cash. You can sell those bonds if certain stocks that you like get cheap enough and could convert those treasury bonds into stocks that you might wanna buy if things get really cheap.” – Tom Dupree

From 2000 to 2013—a full 13 years—the NASDAQ’s total return was just 1%. Not 1% per year. One percent total.

“From 2000 to 2013, the total return for the NASDAQ was 1%, not 1% annualized. 1%.” – Mike Johnson

This sobering statistic illustrates why sequence of returns risk matters so much in retirement. If you experienced that period while withdrawing from your portfolio, the impact would have been devastating. Very few current investors have experienced such an extended period of poor returns, which makes complacency particularly dangerous.

If markets experience significant selling pressure, we typically see a “flight to quality” where investors move from stocks to bonds. This dynamic causes bond yields to fall and prices to rise—exactly when having bond positions provides both stability and profit.

Additionally, the Federal Reserve’s actions matter. While the Fed doesn’t directly control long-term rates, their policies influence the entire yield curve. Recent indications suggest the Fed may stop the runoff of their balance sheet and potentially resume purchases (a form of quantitative easing), which would support bond prices.

The key insight for retirees is simple but crucial: down markets are only an opportunity if you’ve prepared for them.

“Down markets are only an opportunity if you’ve planned for it or if you’ve taken steps to actually be able to take advantage of a down market.” – Mike Johnson

If you’re fully invested in index funds with no bonds, no money market reserves, and no plan to rebalance, you can’t take advantage of discounted prices. You’re simply riding the volatility with no ability to act.

Our approach focuses on:

Income-focused investing doesn’t mean sacrificing growth. Many dividend-paying companies in our portfolios have delivered strong price appreciation while also raising their dividends year after year.

This creates two paths for inflation protection:

The combination provides purchasing power protection without requiring you to sell shares at potentially disadvantageous times.

Market environments change, and successful investing requires adapting to those changes. What worked brilliantly from 2010 to 2021—simply buying index funds and holding—may not serve retirees well in the current environment.

Our research-driven approach, focus on valuation discipline, and tactical use of different asset classes (stocks, bonds, cash) are designed to navigate varying market conditions while keeping your retirement objectives as the North Star.

Market Context: Elevated valuations across major indices, with the Shiller PE at levels similar to 1999, suggest caution is warranted.

Strategic Positioning: We’ve been taking profits and building bond positions to create tactical opportunities and downside protection.

Bonds as Offensive Weapons: Today’s bond purchases can provide price appreciation if rates fall, locked-in 4% yields, and liquidity for future stock purchases.

Historical Perspective: The NASDAQ’s 1% total return from 2000-2013 reminds us that extended periods of poor performance do happen.

Retirement Focus: Our dividend-focused, value-conscious approach aims to generate consistent income with less volatility than pure index investing.

Markets will always have periods of volatility. The question isn’t whether they’ll occur, but whether you’re positioned to weather them and potentially benefit from them.

At Dupree Financial Group, we believe that understanding what you own and why you own it—combined with tactical positioning based on valuations—provides the best path for retirement security.

If you’re wondering whether your portfolio is properly positioned for the current environment, we’re here to help.

Ready to discuss your portfolio positioning?

The Financial Hour airs weekly. Subscribe to stay informed about market developments and retirement planning strategies.

About Dupree Financial Group

With 47 years of investment experience, Tom Dupree and the team at Dupree Financial Group focus on making your money work for you through research-driven, value-conscious investment management. We specialize in creating income-focused portfolios designed to last through retirement.

Dupree Financial Group | Where We Make Your Money Work For You

The post Market Volatility 2025: Why Strategic Bond Investment Can Protect Your Retirement | Dupree Financial appeared first on Dupree Financial.

This episode of the financial hour is from March 29, 2025 – recorded less than a week before the major market volatility and reaction to Liberation Day on April 2, 2025.

In today’s unpredictable market environment, having a clear investment plan is more critical than ever. The recent Financial Hour with Tom Dupree and Mike Johnson discusses why many investors struggle during market downturns and how focusing on income-generating investments can provide stability through market volatility.

As Tom explains, “Market volatility can lead to extremes on both sides. One extreme is that they abandon everything, abandon all hope, sell everything, go to cash. The other extreme is that you do absolutely nothing.”

Many people confuse having a savings plan with having an investment plan. According to Tom Dupree, there’s a critical distinction between the two:

“Some people say, sure. I have a plan. I’m putting X amount into my 401k. I’m putting money into a Roth. I’m putting it into this, to that. That’s not an investment plan. That’s a savings plan. Two completely different things.”

A robust investment plan isn’t just about where you put your money—it’s about having a strategy for how that money will work for you, especially during retirement when you need income.

The Dupree Financial Group follows a clear, two-part investment plan:

“Our investment plan is to first produce an income stream through dividends and interest payments. And then secondly, capital appreciation. We achieve this through using publicly traded securities held at reasonable valuations.”

This approach focuses on:

Many investors, particularly those with 401(k) plans, are heavily invested in growth-oriented funds that mirror the S&P 500. While this strategy can work during accumulation years, it presents serious challenges during retirement:

“We may not feel like you’re equipped to set out and lay out every element of your investment plan. That’s where we can come in and help you because we do this and it’s not an investment plan that operates in a vacuum. This investment plan is designed to throw off income for you on a regular basis.”

Dividend investing provides several advantages for retirees:

“Well, at least you’re getting paid while you wait. See, that’s the good thing about dividends. At least it’s paying you while you wait for it to either grow or just go sideways, you’re getting some kind of income.”

In today’s challenging market environment, it’s essential to:

“Don’t let what’s going on in the market prevent you from making changes, actually examine and say, okay, what’s going on with my portfolio right now is a symptom of a misinvestment or an investment mix that doesn’t work with my situation anymore.”

Is market volatility causing concern about your retirement portfolio? The team at Dupree Financial Group can help you develop a resilient investment plan focused on generating income through dividends and interest payments.

Contact Dupree Financial Group today for a portfolio analysis that can identify risk and opportunity in today’s challenging market. Call us at 859-233-0400 or schedule an appointment directly on our homepage at dupreefinancial.com.

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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 why personalized investment management is essential for pre-retirees aged 50-65. Unlike mass-market approaches from large firms, Dupree Financial Group provides direct access to portfolio managers who understand your specific retirement goals and risk tolerance.

This evergreen financial education episode delivers timeless wisdom on risk assessment, portfolio protection strategies, and why understanding what you own is critical before retirement. Whether you’re working with a local financial advisor in Kentucky or managing investments on your own, these insights will help you make more informed decisions about your retirement security.

The episode draws heavily from Howard Marks’ influential 2006 memo on risk, which Tom and Mike have studied extensively. Marks, co-founder of Oaktree Capital Management, challenges conventional thinking about risk and return relationships.

“If more risk always meant more return, it would cease being risky. The risk would be riskless,” explains Mike Johnson, highlighting the fundamental misunderstanding many investors have about the risk-return relationship.

The discussion emphasizes that bearing risk unknowingly represents one of the biggest mistakes pre-retirees can make. This is particularly relevant for those who have experienced strong market performance for years without understanding the volatility embedded in their portfolios.

Tom Dupree shares a cautionary tale that every pre-retiree should hear:

“There was a man that came to me years ago who had been at UK for a number of years. He had invested in Fidelity and TIAA-CREF, good funds, great returns. He had something like 1,000,006 and he had averaged 13 and a quarter percent return per year for like 23 years. He extrapolated that he could take 10% a year, which was $160,000, live on it and be okay because it was gonna keep doing that. The sequence of returns turned around and bit him good.”

This example perfectly illustrates sequence of returns risk—a critical concept for anyone approaching retirement. Even with excellent average returns, the timing of market downturns relative to when you need to withdraw funds can devastate a retirement plan. This is why personalized investment management from a local financial advisor who understands your specific timeline is so valuable.

The episode challenges the traditional definition of investment risk as merely volatility. For pre-retirees and retirees specifically, Mike Johnson explains:

“The base case that we’re trying to solve here? We’re speaking specifically to near retirees and retirees. Volatility is gonna be your friend or your foe the day you need to take your money out. That’s gonna be your definition of risk—what has the volatility done to my money the day I need it.”

One of the most powerful concepts discussed is how prolonged positive market performance can numb investors to risk—exactly when they should be most vigilant.

Mike Johnson references Nassim Taleb’s “Fooled by Randomness” to illustrate this danger:

“Reality’s far more vicious than Russian roulette. First, it delivers the fatal bullet rather infrequently, like a revolver that would have hundreds or even thousands of rounds instead of six. After a few dozen tries, one forgets about the existence of a bullet under a numbing false sense of security. One is thus capable of unwittingly playing Russian roulette and calling it by something alternative: low risk.”

This perfectly describes the situation many pre-retirees face today after years of strong market performance. The analogy to driving at 90 mph—where you stop feeling the speed—resonates powerfully. You’re taking significant risk, but you’ve become accustomed to it and no longer perceive the danger.

Unlike large firms where you’re assigned an investment counselor who may change frequently, Dupree Financial Group provides direct access to portfolio managers Tom Dupree and Mike Johnson. This relationship-focused approach enables:

“When our clients understand what’s in their portfolio and why, they don’t call us panicking when the market drops,” Tom Dupree emphasizes, highlighting the value of education and transparency in financial relationships.

The episode delivers a sobering message about the limitations of index fund investing for retirees:

“If you don’t like risk and you think that you’re not taking any risk by investing in the S&P 500, sweetie pie, you need to get in the money market fund and just hope you got enough money to ride through it because you are taking risk that you don’t know about. And that is a problem because you’re gonna find it out in a very uncomfortable way at some point.”

This doesn’t mean index funds have no place in portfolios, but rather that they shouldn’t be confused with a comprehensive retirement income strategy. Personalized portfolio analysis considers:

For younger investors just starting out, Mike Johnson offers this perspective:

“If somebody’s in their late twenties, early thirties and they have a few stocks here and there, that’s great. You’re ahead of the curve from a lot of people, but that is not a portfolio. What you want to do is lay a foundation that’s more sturdy, more solid than just having a few stocks here and there.”

This guidance is equally relevant for pre-retirees who may have accumulated individual positions over time without a cohesive strategy. Kentucky retirement planning requires transitioning from an accumulation mindset to a distribution strategy—and that requires professional portfolio architecture.

One of the most important insights for pre-retirees:

“Remember, it’s not just the accumulation, it’s not the dollar amount, it’s what it’s gonna produce for you and how long can it produce that to sustain you. Retirement has the normal set of rules plus other variables that you have to take into consideration.”

This shift in perspective—from portfolio value to sustainable income—is where personalized investment management becomes critical. Every individual’s situation differs slightly, and those differences matter enormously in retirement planning.

Tom Dupree introduces an often-overlooked dimension of investment risk: the role of faith. Not just faith in markets or historical returns, but a deeper consideration of existential risk and what you ultimately trust.

“Underpinning any investment scheme is faith. At the base of everything related to risk is faith. You cannot get away from it. One of the things about the God factor is that it takes certain elements of risk that you’re willing to take on for yourself and transfers them to a higher power.”

While this dimension is personal and not emphasized in typical financial planning, it reflects Dupree Financial Group’s holistic approach to understanding clients as people—not just portfolios.

The biggest risk for pre-retirees is sequence-of-returns risk—experiencing market downturns just as you begin withdrawing from your portfolio. Even with strong average returns over time, poor returns in the years immediately before and after retirement can devastate your retirement security. This is why personalized retirement planning in Kentucky focuses on more than just average returns.

For retirees, risk is primarily defined by volatility’s impact on withdrawals. When you need to take money out during a market downturn, you crystallize losses and reduce your portfolio’s recovery potential. Younger investors have time to recover from volatility. As Tom Dupree explains, “Volatility is gonna be your friend or your foe the day you need to take your money out.”

Index funds are not inherently “safe” for retirement—they carry significant volatility and concentration risks (especially in large-cap tech stocks right now). While they can be part of a retirement strategy, they should not be confused with a comprehensive income plan. Local financial advisors can help design strategies that balance growth needs with income stability.

There’s no universal answer—withdrawal rates depend on your portfolio composition, risk tolerance, retirement timeline, and income needs. The gentleman in Tom’s example assumed 10% annual withdrawals based on historical 13.25% returns, which proved disastrous. Personalized portfolio analysis determines sustainable withdrawal rates specific to your situation.

Local advisors like Dupree Financial Group provide direct access to portfolio managers who personally manage your investments, rather than being assigned to a counselor who may change. You receive personalized service, education about your holdings, and strategies tailored to your specific goals—not mass-market approaches. Tom emphasizes: “When our clients understand what’s in their portfolio and why, they don’t call us panicking when the market drops.”

Knowing what you own means understanding not just the names of your holdings, but the specific risks each position carries, how they work together, and why each was selected for your situation. It means knowing what could go wrong with each investment and having conviction in your overall strategy during market volatility.

Pre-retirees should review portfolio risk at least annually, and more frequently as retirement approaches. Risk tolerance, time horizon, and income needs change as you near retirement. Kentucky retirement planning professionals continuously monitor holdings for emerging risks and rebalance as needed.

Concentration risk occurs when your portfolio has too much exposure to a single stock, sector, or asset class. Many investors have unknowingly accumulated concentration in large technology stocks through both index funds and individual holdings. If that sector declines, your entire portfolio suffers disproportionately. Diversification addresses concentration risk.

Signs you may have excessive risk include: heavy concentration in stocks after years of strong returns, high portfolio volatility relative to your withdrawal timeline, lack of income-producing assets, or simply not understanding what you own. A complimentary portfolio review with Dupree Financial Group can identify hidden risks: call 859-233-0400.

Dupree Financial Group focuses on building long-term relationships with people—not just managing money. The team conducts their own research, provides comprehensive education, thinks independently rather than following the crowd, and designs portfolios around your specific goals. Learn more about their investment philosophy.

Don’t Wait for a Market Downturn to Discover Hidden Risks in Your Portfolio

If you’re retired or approaching retirement, understanding the specific risks in your portfolio is critical. After 47 years in the investment business, Tom Dupree has seen countless retirees discover they were taking far more risk than they realized—often at the worst possible time.

Dupree Financial Group offers Central Kentucky residents a complimentary portfolio review to help you:

Call 859-233-0400 to schedule your complimentary consultation

Or visit us online:

Dupree Financial Group serves clients throughout Central Kentucky, including Lexington, Louisville, Frankfort, Winchester, Richmond, and surrounding communities.

The Tom Dupree Show provides timeless financial education for investors approaching and in retirement. Hosted by Tom Dupree, Jr., founder of Dupree Financial Group, and portfolio manager Mike Johnson, each episode delivers practical insights on investment management, retirement planning, and portfolio risk assessment. Unlike generic financial advice, the show focuses on the specific challenges facing Kentucky retirees and pre-retirees.

Tom Dupree founded Dupree Financial Group on the principle that creating long-term relationships with people—not just their money—is the key to successful wealth management. With direct access to portfolio managers and personalized investment strategies, Dupree Financial Group delivers the attentive service of a local advisor with the knowledge of a seasoned investment team.

Episode Type: Evergreen Financial Education

Primary Topics: Investment Risk, Retirement Planning, Portfolio Management, Sequence of Returns Risk

Featured Guests: Mike Johnson, a member of the team at Dupree Financial Group

Listen to More Episodes: Market Commentary Archive

Help others understand investment risk by sharing this episode: www.dupreefinancial.com/podcast

The post The Hidden Investment Risks You Don’t See Coming: Kentucky Retirement Planning Insights appeared first on Dupree Financial.

In today’s volatile market environment, pre-retirees need more than autopilot investing—they need personalized investment management with direct access to portfolio managers who actively monitor risk. In this episode of The Tom Dupree Show, Tom Dupree, Jr., Mike Johnson, and Hudson Kemp discuss why active portfolio management is critical for retirement success, especially when the S&P 500 reaches record highs and market valuations signal increased risk.

Unlike large financial firms that rely on quarterly rebalancing and assigned investment counselors, Dupree Financial Group provides Kentucky retirement planning with a team approach that monitors portfolios daily. This episode reveals why understanding what you own—not just how much you have—makes the difference between panic-selling during downturns and confident retirement living.

With the Dow and S&P 500 reaching record highs despite predictions of market meltdowns, many investors wonder whether to stay invested or move to safety. Mike Johnson explains the current market environment:

“Markets like to climb a wall of worry. You’ve had that since April when value abounded. You could almost throw a dart in April and buy something that was good. The market is up more than 25% since then. But what you’ve had is a shift from total risk-off to now risk-on across asset classes, and it gives us pause.”

This transition from cautious to euphoric investing signals danger for retirement portfolios. As Hudson Kemp notes, the “me too money” piling into markets at peak valuations creates vulnerability that retirees cannot afford.

When asked to rate current market risk on a 1-10 scale, Mike Johnson placed it at 8-8.5- primarily due to elevated price-to-earnings ratios. This assessment drives Dupree Financial Group’s current strategy of profit-taking and repositioning into government bonds and undervalued dividend-paying stocks.

“When you’ve had a period of higher than average returns, you expect the future returns to be less. If you have a stock that was trading at 80 and it goes to 50, is it more or less risky at 50? Typically it’s less risky at 50. If you have a stock that goes from 50 to 80, it’s probably more risky at 80 because it’s priced for perfection.”

Hudson Kemp shares a revealing conversation with a friend whose financial advisor makes portfolio adjustments quarterly—a stark contrast to Dupree Financial Group’s daily monitoring approach:

“I have a friend who had a meeting with their advisor two days ago. I gave them some questions to ask, and one was: how often do you make adjustments in my portfolio? That advisor makes those adjustments on a quarterly basis. Compare that to what we’ve just discussed—active portfolio management where we are watching every move in the market and making moves when opportunities arise.”

This difference becomes critical during volatile periods. When China tariff announcements or Federal Reserve decisions move markets, quarterly rebalancers miss opportunities while active managers can capitalize immediately.

Mike Johnson describes a recent example of active management timing:

“That Friday morning is when we added to our 30-year treasuries. That afternoon is when the issue happened with China—just a big long tweet—and then the market sold off because of that. Every day you’re going to have something happening, and what we have to be careful of is getting in on the ‘me too’ train just because everybody else is.”

This kind of tactical positioning protects retirement assets while maintaining upside potential—something passive strategies simply cannot deliver.

While most financial advisors push asset allocation models designed for accumulation, Kentucky retirement planning requires a different approach. Tom Dupree explains the philosophy:

“We’re trying to look through the noise, the day-to-day noise, and not get caught up in the momentum. Whatever the momentum is on any given day. If the momentum’s up, you don’t want to take part in that. If the momentum’s down, that’s when you typically want to be buying. We’re in an environment now where things are going up, so we’re taking some profits off the table.”

Hudson Kemp highlights what surprises many new clients during personalized portfolio analysis:

“After five to 10 years, you get to see that income actually surpasses the appreciation and the value of the shares that you own. It’s a long-term play, but it’s amazing to see over time when you talk to clients who have been invested with us for 10 years or 15 years or 18 years—where you can see the numbers laid out that way.”

This income stream “cranks in the background,” as Mike Johnson describes it, providing stability during market downturns that growth-focused portfolios cannot match.

Unlike mass-market firms that rely on pre-packaged ETFs, Dupree Financial Group conducts direct research with company management teams. This hands-on approach provides insights that drive better investment decisions.

The team recently invested in two food companies with different profiles—one international giant and one smaller U.S.-based company that has declined 34% this year. Tom Dupree shares why:

“The food space has gotten very compressed in terms of profit margins. Things related to food have gotten to be a much tougher business. This stock has gone down 34% this year. Will it be an immediate turnaround? Probably not, but it has a decent yield, and your risk at this price is a lot lower versus where it was at the beginning of the year.”

He recalls visiting the international food company’s Switzerland headquarters, where the CFO made a memorable promise about dividend continuity:

“We asked him, would you ever discontinue the dividend? He said, ‘You see that lake out there? They would take me 300 yards out, put concrete around my legs and throw me overboard. I will never cut that dividend.’ People in Switzerland and in Europe live off dividends—that’s why so many stocks over there pay dividends and they pay them faithfully.”

While acknowledging AI’s transformative potential, the team approaches this volatile sector carefully. Mike Johnson explains:

“We’ve had a lot of calls learning about the AI sector, just trying to get our minds around that. We’ve made a couple small investments—small in terms of percentage of the portfolio—but we’re getting more comfortable with what they do. We also acknowledge and realize the volatility inherent right now in those areas.”

This measured approach contrasts sharply with advisors recommending aggressive AI sector concentration—a strategy that may work for young accumulators but creates unacceptable risk for pre-retirees.

One of the most common questions Hudson Kemp hears from new clients during their complimentary portfolio review:

“A large number of the clients I’ve met with leave off the portfolio review with: ‘Why don’t more people do this? Why do more people not understand what you do here?’ Because that’s the largest part of it—the income side of what we do.”

Many investors hold ETFs without knowing the underlying companies or their valuations. Tom Dupree explains the problem:

“If you’re invested in an off-the-shelf ETF where there’s probably a large AI exposure, who knows what companies are in there, what they do? A lot of times the actual client doesn’t even know what companies they own. That’s what comes back to what we do here—we make sure that you know what you own.”

This knowledge prevents panic-selling during downturns. As Mike Johnson notes:

“One of the biggest compliments that clients can pay to us is: ‘I don’t worry about it.’ Our phones don’t ring off the hook when the market’s dancing around either. Typically the phone calls we get when markets are choppy are people calling in saying, ‘I want to come in’—these are not clients, these are prospects who realize they have risk in their portfolio.”

Many pre-retirees operate on financial autopilot, hoping everything works out. Tom Dupree addresses this directly:

“If you have no idea what you actually own in your 401k, you’re not alone. We meet with Central Kentucky folks every week who’ve been on autopilot for years. After 47 years in the investment business, I can tell you this: people get most afraid about stuff they don’t understand. When our clients understand what’s in their portfolio and why, they don’t call us panicking when the market drops.”

Mike Johnson describes how the team stays ahead of market opportunities:

“Some of the companies we’ve had calls with, we’ve not invested in yet, but we’ve had calls learning about the business. We think we have a pretty good understanding of what they do and what a reasonable valuation would be. The reason you do that in periods like this is so that when you have that period of volatility, you can go back and say, ‘This is company A—it looked a little expensive when we talked to them. Now valuation has come down. That’s where I want to be.'”

This preparation allows tactical positioning that passive strategies cannot match—protecting retirement assets while capturing opportunities others miss.

One of the most dangerous assumptions pre-retirees make involves extrapolating past returns into the future. Mike Johnson references a critical concept discussed in their evergreen educational episode:

“Somebody averaged 13% over a long period of time, but then they retired, assumed they could take out 10%, and then you got into bad sequence of market returns. That’s why we’ve been pounding the table: when the numbers work for you, assess the risk that’s in your portfolio and make adjustments that fit with where you are in life.”

For a 55-year-old nearing retirement, a 25% market correction followed by slow recovery creates dramatically different outcomes than the same scenario for a 30-year-old with decades to recover.

Mike Johnson reveals why most financial advisors push asset allocation over income-focused strategies:

“The industry is geared towards asset accumulation. Being a conventional thinker—that’s dangerous from an investment standpoint, but from an asset gathering standpoint, that’s a pretty comfortable place to be. We try to avoid that, not just for the sake of being contrarian, but because we think it’s a better approach for retirement investments. It’s more legwork than just doing a risk tolerance questionnaire and putting it in an asset allocation mix.”

Tom Dupree explains the fundamental mismatch:

“When you’re in the retirement years, that’s where you get the rubs. You’ve got a certain goal in mind—if it’s for income—but then an asset allocation model isn’t producing income and is more reliant on growth. That’s where the rub comes in. Typically, asset allocation models are heavier on growth buckets and not as much on income.”

This structural problem forces many retirees to sell appreciated shares during downturns to generate income—the worst possible timing.

In a powerful moment, Tom Dupree addresses the deeper foundation needed for financial peace:

“Money is not everything. Your faith needs to be in something bigger than what’s in your account. We act like our accounts are there forever. Warren Buffett has in his office a big bunch of newspaper headlines where the markets dropped a lot. You need to have faith in something bigger than just what’s in your money. You need to have faith in God. That’s what has caused me to keep moving in this business all these years. I don’t want to go out and preach to people about how great the market is and it’s going to fix all your problems—because it’s not. You have to think in terms of something bigger than money.”

Mike Johnson reinforces this perspective:

“Some of our clients teach us more about the principles we’re talking about than we do them. That’s one thing Hudson does exceptionally well—he listens. Over the years, you listen to the clients and everybody has a different story. Successes, failures. There’s so much wisdom that we’ve been able to gather from our clients. It’s been a lifetime impact from things I’ve been able to learn from our clients.”

The team provides specific guidance on when new clients should expect their portfolios to be invested in current market conditions:

“If you bring an account to us right now, we’re going to spend some time getting it invested. Depending on what the market does next month, or Monday or Tuesday—you just don’t know. You don’t want to get caught up in the momentum.”

Tom Dupree outlines current strategy:

“We’ve retreated to buying government bonds. We bought quite a few of them because we do believe over time that the inflation rate is going to come down even lower, and it’s going to bring the price of treasury bonds up. I don’t believe there’s anybody out there who would say this market is perfect and that we’re just going to keep going higher.”

This positioning protects against downside while maintaining exposure to quality dividend payers that have pulled back from recent highs.

Dupree Financial Group’s team structure provides advantages that assigned investment counselors at large firms cannot match. Tom Dupree explains:

“It’s always good to have new ideas, fresh minds. That’s why we have a team—Hudson, James Clark. They’ve brought ideas. We’ve had a lot of calls learning about the AI sector, just trying to get our minds around that. Hudson was talking about a company this morning in the real estate area. We’re going to schedule a call with them and we’ll learn something. Who knows, maybe we will invest in it, but at the very least we’ll learn about it.”

“The other interesting thing about talking to companies and the research that is done at Dupree Financial Group: oftentimes if we’re talking to a company about what they do, we learn something maybe we didn’t think we would learn, which leads us to think about another path. Then we talk to another company as a result of that path. It’s just continuous learning—it always makes one better. Doesn’t matter what it is you’re learning about.”

If you don’t know what you own in your portfolio, you need to—and we can help.

At Dupree Financial Group, we provide Kentucky retirement planning with a team approach that puts you first. Unlike large financial firms that assign you to an investment counselor working from standardized models, you get direct access to portfolio managers Tom Dupree, Jr., Mike Johnson, and Hudson Kemp—professionals who actively monitor your investments daily, not quarterly.

After 47 years in the investment business, Tom Dupree has learned one critical truth: people get most afraid about stuff they don’t understand. When our clients understand what’s in their portfolio and why, they don’t panic when markets drop—they have confidence in their retirement plan.

Call us at 859-233-0400 for your complimentary portfolio review, or schedule an appointment directly on our website.

Learn more about our investment philosophy and approach:

Dupree Financial Group: Where We Make Your Money Work for You

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The post Financial HOUR 10-18-25 appeared first on Dupree Financial.

The post Financial Hour 10-11-25 appeared first on Dupree Financial.

When government shutdowns dominate headlines and market bubbles threaten portfolios, Central Kentucky investors need clear guidance from experienced financial advisors. Tom Dupree Jr. and his team at Dupree Financial Group cut through the noise to explain what really matters for your retirement planning.

In this episode of the Financial Hour, our Kentucky-based investment managers analyze current market conditions, explore the risks of AI speculation, and reveal why personalized investment management beats mass-market approaches every time.

Despite media hysteria, government shutdowns historically have had minimal impact on investment portfolios. Since 1976, there have been 11 government shutdowns, with the longest lasting 35 days (December 2018-January 2019).

Key market performance during that shutdown:

“As investors, you have to look through the noise. It’s a material event, but from an investment standpoint, at least right now, it’s kind of a non-event,” explains Tom Dupree Jr.

Government furloughs remind every investor—regardless of employment—of a critical planning principle: emergency funds are essential. Whether you’re a federal employee or private sector worker, your financial plan should account for income disruptions.

Emergency planning essentials:

While everyone focuses on tech stock valuations, experienced portfolio managers are watching more troubling indicators in fixed income markets.

Corporate bond spread compression reveals dangerous optimism:

“You should be paid to take that extra risk, and right now you’re not.”

The rapid expansion of asset-backed securities (ABS) tied to speculative ventures mirrors pre-financial crisis conditions:

“When you have something like that… you’ve got all these derivatives tied to that. It’s kind of a house of cards. You have one small thing happen, and it sets off a firestorm.”

Going all-in on trending sectors works for some young investors with time to recover, but it’s dangerous for retirement accounts.

Risk considerations:

Selling everything and moving to cash requires being right twice: when you sell AND when you buy back in.

“I have never seen that work out well. What you usually see is people jump out at the bottom and then jump back in after they feel it’s safe, which is after it’s already gone way back up.”

Hidden costs of timing:

Passive approaches work for young dollar-cost-averaging investors, but retirees need more sophisticated strategies.

Direct access to portfolio managers who conduct proprietary research enables nimble responses to market conditions.

Diversification advantages:

Mass-market firms assign you to investment counselors following centralized mandates. Dupree Financial Group offers something dramatically different.

Direct access means better outcomes:

“We don’t have to call New York. We don’t have to call places to find out what they’re seeing. We’ve already talked to the companies ourselves,” notes the team.

As fiduciaries, Dupree Financial Group is legally obligated to put your interests first—not just recommend “suitable” products that benefit the firm.

“Three of our best investments this year came from discussions about another company. The constant dialogue is important, but it wouldn’t be happening if we weren’t doing the research.”

Short-term trading requires precise timing and creates unlimited risk exposure (especially with shorts). Long-term investing in quality companies aligns with how businesses actually operate.

Multi-decade business horizons:

Proprietary research builds sector competencies that reveal opportunities invisible to index-following competitors.

“You build up competencies in those areas. That’s why the research is so important—it uncovers opportunities but also solidifies the investment thesis for when things get choppy.”

Dividend-paying stocks create cash flow during volatility, funding retirement needs while waiting for market recovery.

Q: How do I know if I’m overexposed to market bubbles?

A: If you don’t know what you actually own in your 401(k) or investment accounts, you need a personalized portfolio analysis. Many investors discover surprising concentrations in overvalued tech sectors.

Q: What makes Dupree Financial Group different from national firms?

A: Direct access to portfolio managers, in-house research, fiduciary responsibility, and deep roots in Central Kentucky. Learn more about our investment philosophy.

Q: Should I sell everything before the next crash?

A: Market timing rarely works. Strategic diversification, quality companies, dividend income, and proper asset allocation provide better risk management without requiring perfect timing.

Q: How important are emergency funds for retirees?

A: Critical. Even retirees should maintain liquid reserves for unexpected expenses, market downturns, or opportunities to rebalance at attractive valuations.

Q: Where can I learn more about current market conditions?

A: Listen to our weekly podcast in the Market Commentary archive for ongoing analysis of economic trends and investment opportunities.

After 47 years in the investment business, Tom Dupree Jr. has seen what happens when investors don’t understand what they own. Don’t let autopilot investing jeopardize your retirement.

Get your complimentary portfolio review from Central Kentucky’s retirement fiduciary advisors:

Dupree Financial Group serves pre-retirees and retirees throughout Central Kentucky who want personalized investment management, transparent communication, and direct access to experienced portfolio managers.

Stop guessing. Start knowing. Your retirement deserves better.

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