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.

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