The Tom Dupree Show

Building a Financial Advisory Firm That Puts Clients First: An Inside Look at the Process Meta Description: Discover why Tom Dupree founded Dupree Financial Group in Lexington, Kentucky—focusing on personalized investment management, team accountability, and retirement planning for local clients. For pre-retirees and retirees in Kentucky searching for personalized investment management, understanding the “why” behind your financial advisor matters just as much as the “how.” In this special episode of The Financial Hour of The Tom Dupree Show, Tom Dupree Jr. and Mike Johnson share the founding story of Dupree Financial Group—a journey that began with a simple walk in the woods near Natural Bridge in Kentucky in February 2002 and evolved into a comprehensive wealth management approach designed specifically for Lexington-area retirement investors. The Origin Story: From Brokerage Dissatisfaction to Independent Registered Investment Advisor Tom Dupree recalls the pivotal moment that sparked the creation of Dupree Financial Group. Walking through the woods with his young son James on his shoulders, he realized the traditional brokerage firm model wasn’t aligned with the future he envisioned for his family and clients. “I got this joy, this excitement in my heart thinking about doing this,” Tom explains. “I was in no position to do it at all. I didn’t have any money. Strangely, my banker approved me for a loan to actually go get the office space and get it fitted up. And that fit-up is still the same fit-up we’re using. We have not changed it.” The firm officially opened in 2003, but Tom identifies 2010 as the true beginning of Dupree Financial Group as it exists today. That’s when the firm disassociated from an outside brokerage and became an independent Registered Investment Advisor (RIA). “In 2010, we disassociated ourselves with an outside brokerage firm and became what’s called an RIA, a Registered Investment Advisor, which meant that now we’re not paying 25% of our revenues to an outside firm,” Tom shares. “That enabled us to do a lot more internally, and it really was the beginning of the firm that we know today.” Key Takeaways: Why Dupree Financial Group Started Client-focused mission: Created to serve average retirement investors who wouldn’t necessarily get attention from major brokerage firms Cost structure advantage: Lower overhead means smaller accounts receive meaningful attention and personalized service Local accountability: Designed specifically to respond to clients in Lexington, Kentucky, and the surrounding region Team approach: Built from the ground up to provide collaborative service rather than single-broker relationships Independence: Becoming an RIA in 2010 eliminated the pressure to use proprietary products and allowed true fiduciary responsibility Personalized Investment Management vs. Mass-Market Approaches One of the core distinctions Tom emphasizes is the difference between Dupree Financial Group’s model and the mass-market approach taken by larger national firms. Rather than assigning clients to investment counselors within a large hierarchy, Dupree Financial Group provides direct access to portfolio managers who actually research and select the investments. “When you’re talking to somebody, to one of us, the team that you’re talking to is also the team that is designing your investment portfolio, actually helping pick stocks and bonds to own in the portfolio,” Tom explains. “Now why is that a big deal? Well, when I was with Brand X, they had a guy in New York who was brilliant, and he really was brilliant, and he was a stock picker. You didn’t ever talk to him, but he would publish a list of things that you ought to buy.” That approach failed catastrophically during the 2001-2002 market downturn, when many clients saw portfolios decline 50% with little communication or accountability from their advisors. “It wasn’t so much the fact that everything went down, although that was a big part of it, but it was the lack of communication,” Tom notes. “It was not being willing to be accountable for what really had happened, and they just clammed up.” The Dupree Difference: Direct Access and Transparency Mike Johnson highlights several critical advantages of the Dupree Financial Group model: Team collaboration: Multiple professionals work together on research and portfolio management, producing better outcomes than single-advisor approaches Direct communication: Clients speak directly with the team members who make investment decisions Own investment selection: The firm conducts its own research and calls companies directly rather than relying on buy lists from headquarters Local presence: All revenues stay local and are reinvested in client services rather than flowing to Wall Street firms “The service team is way more aligned with the investment team,” Mike explains. “It’s not two separate functions sitting in the same room.” Investment Philosophy: Focus on Income and Risk Mitigation for Kentucky Retirement Planning Unlike money managers competing to beat specific indices, Dupree Financial Group takes a different approach focused specifically on retirement investors’ needs. This investment philosophy prioritizes income generation and risk mitigation over performance rankings. “We’re not trying to beat any index. We’re just investing in things that we see are good that we think meet our parameters for what we’re looking for,” Tom states. “The why is it’s a focus on risk mitigation, and it’s a focus on income. Those things actually make it pretty easy for us once we tie down the parameters of what we’re looking for.” Mike Johnson references a quote from investment manager Howard Marks that encapsulates a key industry problem: “If you want to be in the top 5% of money managers, you have to be willing to be in the bottom 5% too.” That statement, Mike explains, highlights the perverse incentives created when advisors chase index performance rather than focusing on actual client needs. Real Portfolio Examples: How the Strategy Works The team shares several examples of their investment approach in action: The 6.5% Dividend Stock: “We bought it in June. This company, our listeners would be familiar with. At the time, it had a six-and-a-half percent dividend yield, and the valuation was attractive when you look at the hard assets that they had. We felt some things could go right for the company over the next couple of years. And in the meantime, the stock had gone down significantly, so there was a lot of bad news priced in already. Since then, the stock has gone up to what we thought it would go up to over the next two to four years. It just did it in four months.” The Grocery Company: “We invested in a company the other day—it was a grocery company well known within Central Kentucky. It’s gotten cheap. We just knew it as being a household name that pays a small dividend.” The Clothing Brand: “It’s kind of a clothing company, well-known. It puts out some major, well-known brands. The thing’s gone from a hundred dollars to 30-something, so we decided to take a look there. That one pays a pretty good dividend.” These examples demonstrate the value-focused, income-oriented approach that differentiates Dupree Financial Group from index-chasing strategies. The Team Approach: Building Long-Term Relationships Over Transactions A fundamental principle at Dupree Financial Group is the shift from transactional relationships to ongoing partnerships. Tom explains how his years at major brokerage firms taught him what he didn’t want to replicate. “One thing that I learned in the big firms was that it’s always about the transaction. It’s about the trade,” Tom recalls. “You were constantly having to pursue that trade, do this trade with this client, do that trade with that client. I didn’t want it to be about the trade anymore. I wanted it to be about the relationship.” This philosophy manifests in several concrete ways: Regular review process: Unlike transactional brokerage relationships, Dupree Financial Group built systematic client reviews into the firm’s DNA from the beginning No pressure to sell: Because clients have already committed to the process, meetings focus on education and information rather than sales Team accountability: Multiple team members take responsibility for each client rather than the single-broker model Transparent communication: When investments don’t work out, the team explains why openly rather than avoiding difficult conversations “When our clients come in for a review or they call with a question, they know we’re not trying to sell them anything,” Mike emphasizes. “It’s informational. It’s actually something they can use.” Direct Company Research: An Uncommon Practice One aspect of Dupree Financial Group’s approach that sets them apart is their practice of directly contacting companies they invest in—something Tom notes is rare among medium and small-sized investment advisors. “We do calls with these companies. In some cases, we’ve gone to visit them—the actual company itself that we’re investing in,” Tom explains. “That would’ve been unheard of in our previous setup. A big part of what we do is talk to the clients—I say clients, the businesses that we invest in. We talk to them, we want to find out what they’re doing, learn a little bit about management and do the best we can to really do our due diligence.” This hands-on research approach provides insights that buy lists and analyst reports simply cannot match. Four Generations of Financial Service: The Dupree Family Legacy The commitment to serving clients runs deep in the Dupree family history. Tom shares how his grandfather entered the investment business around 1920 in Louisville, Kentucky, selling preferred stock for Louisville Gas and Electric directly to the public before moving into municipal bonds. “My grandfather was the first one of our line that was in the investment business,” Tom explains. “Then my dad got into the business after being in the navy, I think it was around 1955 in Harlan, Kentucky. Then me and now my two sons are in the business.” Tom’s father moved the family to Lexington in 1963 and founded Dupree and Company, which managed municipal bond issues and eventually started the Kentucky Tax Free Mutual Fund in 1979. “Their idea was always to make a thing for clients that the clients could use, that was a retail thing,” Tom notes. “And so I carried that concern for the clients into what I did when we started Dupree Financial Group.” This multi-generational focus on creating client-centered investment solutions forms the foundation of the firm’s culture today. Tom’s sons, Clark and James, are involved with Dupree Financial Group, making the fourth generation of Duprees in the investment business. The Evolution: Early Struggles to Established Success Tom is refreshingly transparent about the challenges of the firm’s early years. After opening in 2003, success didn’t come easily or quickly. “It certainly was frightening during those early days of opening the firm and wondering if anybody would ever show up,” Tom recalls. “We did all these seminars, lots of them, over a hundred. People would show up, and now and then we’d get a client out of it. It took a lot of work.” The firm began regular radio broadcasts around 2008, which helped build awareness and credibility in the Lexington community. But the real transformation came in 2010 with the transition to RIA status. “When we became an RIA, it opened up possibilities for investment options that we didn’t have before,” Mike reflects. “It got the pressure of the heavy hand off to use proprietary products. That hand was always on you. And so that was lifted. It was like the skies opened up that you had this flexibility now.” Mike adds a crucial point about this transition: “At the same time, that was a sobering feeling. Now it was on you. You can’t blame it on anybody. But from our client’s standpoint, that was something that was a positive because the accountability increased for the firm.” Client Retention: The Ultimate Validation Perhaps the strongest validation of Dupree Financial Group’s approach is client retention. Tom notes that the firm keeps clients longer and longer—a testament to the relationship-building model. “We seem to be keeping clients longer and longer, so evidently we did something right,” Tom observes. “Once we got the buggy built, we really haven’t fooled with it much. We’ve tried to do some tweaks here and there, but the basic chassis has served us pretty well.” Why the “Why” Matters for Kentucky Retirement Investors For pre-retirees and retirees evaluating financial advisors, understanding the “why” behind a firm’s approach provides crucial insight into what kind of service you’ll receive. Dupree Financial Group’s founding principles remain consistent today: Serve retirement investors who might not get attention from large brokerage firms Maintain local presence and accountability in Lexington, Kentucky Provide team-based service rather than single-advisor relationships Focus on income and risk mitigation rather than index performance Conduct independent research and select individual investments Build long-term relationships rather than pursuing transactions Communicate transparently about both successes and setbacks As Tom reflects: “It really wasn’t about the investment performance. It’s about the touch, it’s about the accountability, those sorts of things. And that’s the kind of thing we’ve set up. That was what I envisioned when I started this thing—that we would give the clients more of what they should have been getting at the Wall Street firms.” Ready to Experience the Dupree Financial Group Difference? If you’re approaching retirement or already in retirement and want a local financial advisor who prioritizes transparency, accountability, and personalized service, Dupree Financial Group invites you to experience the difference that a client-first approach makes. Schedule your complimentary portfolio review today: Call: (859) 233-0400 Visit: www.dupreefinancial.com Get Personalized Analysis: Request your portfolio consultation Don’t settle for mass-market investment approaches or impersonal service from distant Wall Street firms. Work with a team of Kentucky financial advisors who do their own research, communicate directly with you, and keep your retirement goals at the center of every decision. Explore more insights on Kentucky retirement planning strategies and listen to additional episodes in our Market Commentary archive. Frequently Asked Questions About Dupree Financial Group What makes Dupree Financial Group different from large brokerage firms? Dupree Financial Group operates as an independent Registered Investment Advisor (RIA), meaning the firm doesn’t pay commissions to Wall Street parent companies and doesn’t face pressure to use proprietary products. The team that meets with clients is the same team that researches and selects investments, providing direct accountability and transparency. All revenues stay local and reinvest in client services rather than flowing to distant corporate headquarters. Why did Tom Dupree start his own financial advisory firm? Tom founded Dupree Financial Group in 2003 after 19 years with a major brokerage firm, where he witnessed the limitations of the transactional, sales-focused model. He envisioned creating a firm that would serve average retirement investors with personalized attention, team-based accountability, and a focus on long-term relationships rather than individual trades. The firm became truly independent in 2010 when it transitioned to RIA status. What is the investment philosophy at Dupree Financial Group? Unlike money managers competing to beat specific indices, Dupree Financial Group focuses on income generation and risk mitigation for retirement investors. The team conducts its own research, including direct calls to companies they invest in, and selects individual stocks and bonds based on dividend yield, valuation, and margin of safety rather than trying to match or beat market benchmarks. How does the team approach at Dupree Financial Group benefit clients? The team model means clients receive the collective expertise of multiple professionals rather than relying on a single advisor’s perspective. Multiple team members share responsibility for each client account, improving service levels and ensuring continuity. This collaborative approach produces better research outcomes and provides clients with consistent access to knowledgeable professionals. What types of clients does Dupree Financial Group serve? Dupree Financial Group specializes in serving pre-retirees and retirees, particularly those who might not receive personalized attention from large brokerage firms. The firm’s cost structure allows them to provide meaningful, customized service to clients with retirement accounts of various sizes, with a focus on the Lexington, Kentucky area and surrounding regions. How often does Dupree Financial Group communicate with clients? Regular client reviews are built into the firm’s DNA from the beginning. Unlike transactional brokerage relationships where communication happens only when making trades, Dupree Financial Group maintains ongoing dialogue with clients through systematic review processes. These meetings focus on education and information rather than sales, since clients have already committed to the firm’s investment process. Does Dupree Financial Group charge fees or commissions? As a fee-based Registered Investment Advisor, Dupree Financial Group operates under a fiduciary standard, meaning it’s legally required to act in clients’ best interests. This fee-based structure eliminates conflicts of interest inherent in commission-based brokerage relationships and aligns the firm’s success with client outcomes. Disclaimer: This content is for informational purposes only and does not constitute investment advice. Past performance does not guarantee future results. Please consult with a qualified financial professional regarding your specific situation. The post Why Independent Financial Advisors Choose Income Over Index Performance for Retirement Portfolios appeared first on Dupree Financial.

Understanding Market Volatility and Strategic Retirement Investing in 2025 Episode Summary: In this episode of The Financial Hour, Tom Dupree and Mike Johnson, local financial advisors from Dupree Financial Group in Kentucky, talk about current market conditions, Federal Reserve rate cut speculation, and why personalized investment management matters more than ever during periods of high volatility. With Tom’s 47 years of investment experience, he shares insights on protecting retirement portfolios while identifying genuine growth opportunities. Key Topics Covered: Retirement Portfolio Protection in Volatile Markets Market Volatility Analysis: What Kentucky Retirees Need to Know Since the end of October, markets have experienced unprecedented volatility. The NASDAQ saw one of its most dramatic single-day swings on November 20th, surging over 2% before closing down 2.2%. For retirees and pre-retirees managing retirement portfolios, understanding these “toppy market” signals is crucial for wealth preservation. Federal Reserve Rate Cuts: Separating Reality from Market Hype Market sentiment shifted dramatically within a single week when New York Fed President John Williams hinted at potential rate cuts. The probability jumped from 35% to over 80% for a December rate cut. But are these 25 basis point adjustments really moving the needle for everyday investors? Tom offers a refreshingly honest perspective that you won’t hear from your typical 1-800 number investment counselor: “This fed 25 basis point rate cut, it’s bs. So what? It’s not a big deal and they’re only using it to prop up the market and the minute they announce it, the market will sell off.” The Real Housing Market Challenge Unlike generic market commentary, this local financial advisory perspective addresses what’s actually keeping people from moving: it’s not just interest rates. Many homeowners are locked into 2-3% mortgages, and a quarter-point reduction won’t change their calculus. For Kentucky retirement planning, understanding these nuances matters when evaluating portfolio allocation. LNG Infrastructure: A Hidden Opportunity for Income-Focused Investors While everyone chases AI and tech speculation, we are identifying substantial opportunities in liquified natural gas (LNG) infrastructure. This represents the kind of strategic, research-based investing that comes from direct access to portfolio managers rather than cookie-cutter advice. Why LNG Matters for Retirement Portfolios: Predictable Cash Flows: Pipeline companies operate on “take or pay” contracts, providing consistent dividend income Massive Infrastructure Buildout: US LNG export capacity expanding from 19 billion cubic feet/day to 33 billion by 2032 Less Speculative Risk: Unlike AI data centers with uncertain equipment lifespans, natural gas infrastructure offers proven business models Growing Export Market: LNG exports up 21% year-over-year through August 2025 Essential Energy Transition: Natural gas remains critical for power generation, especially for data centers Mike Johnson explains the investment thesis: “You view the AI data center build out with something like LNG and the pipelines that are feeding that—it’s a more consistent, more predictable business model because it’s been around a long time. It’s more predictable. And so when you’re looking at it from an investment standpoint, especially from a retirement investment standpoint, these pipeline companies generally have more predictable, consistent cash flow and their dividends are more consistent.” Key Takeaways for Investors Approaching Retirement Recognize “Toppy Market” Signals: Large upward swings that can’t hold indicate potential market exhaustion Understand Market Broadening: Since late October, equal-weight S&P 500 outperforming tech-heavy indices suggests rotation Don’t Overreact to Fed Announcements: 25 basis point cuts have limited real economic impact Avoid Recency Bias: Just because markets have been rising doesn’t mean they’ll continue indefinitely Consider Real Infrastructure Plays: LNG pipeline expansion offers more predictable returns than tech speculation Protect Gains Strategically: After a strong year, raising some cash in overvalued positions makes sense Plan for Extended Productivity: The “Refire” movement—starting new careers in retirement—provides both income and purpose Understand Your Risk Exposure: Many investors don’t realize how much risk is embedded in their portfolios The Retirement Reality Check: Are You Really Ready? The “Refire” Alternative to Traditional Retirement Rather than completely stepping away from productive work, consider the “Refire” movement—transitioning from a draining career to something you’re passionate about. Dupree Financial Group clients have successfully transitioned into: Construction and farming ventures Specialty craft businesses (like the 87-year-old client working with wool) Consulting in their areas of expertise Gig economy opportunities that provide flexibility and income Why Personalized Investment Management Beats the 1-800 Number Approach This episode perfectly illustrates what sets Dupree Financial Group apart from mass-market investment firms. You’re not getting generic advice from an assigned counselor reading from a script. You’re getting: 47 years of investment experience navigating multiple market cycles Direct access to portfolio managers who actively manage your investments Local financial advisors in Kentucky who understand regional economic factors Honest, straight-talk guidance rather than market cheerleading Proactive portfolio adjustments based on current market conditions Education-first approach so you understand what you own and why Market Wisdom from 47 Years of Experience Tom shares a telling quote about investing psychology: “A man can never be faulted, even if he’s wrong, for the bold and aggressive action in pursuit of victory. A real man must be willing to strike out and go down swinging.” His response? “People are investing like that right now. It’s almost the gambler’s mindset where it’s the recency bias… It’s ignorance. And I don’t mean that in a bad way, it’s just lack of knowledge on what’s embedded in a portfolio.” This is the difference between speculation and strategic retirement investing—understanding what you own, why you own it, and what risks you’re actually taking. Important Reminders for Retirement Investors The Extended Bull Market Risk As Mike notes: “We’ve not had an extended bear market since the financial crisis.” An entire generation of investors has never experienced a prolonged downturn. This creates complacency and excessive risk-taking, particularly dangerous for those nearing or in retirement who don’t have time to recover from major losses. When Fully Valued Markets Present Challenges Mike explains the risk-reward calculation: “When you’re buying something that’s either fully priced or is looking historically at being fully priced, then you’re making a bet that things are gonna keep getting fuller priced.” Translation: You’re hoping a greater fool will pay even more than you did. That’s not investing—it’s speculation. Frequently Asked Questions (FAQs) Should I worry about current market volatility as I approach retirement? Yes, but worry productively. Large intraday swings, particularly when markets can’t hold gains, often signal “toppy” markets. This doesn’t mean selling everything, but it does mean reviewing your portfolio’s risk exposure and potentially raising some cash in overvalued positions. A team of local financial advisors with decades of experience can help you navigate these decisions based on your specific situation, not generic market timing. Will Federal Reserve rate cuts help my retirement portfolio? The impact of 25 basis point rate cuts is often overstated. While they may provide short-term market support, genuine portfolio growth requires earnings growth and sound business fundamentals. Personalized investment management focuses on these fundamentals rather than trying to trade Fed announcements. What makes LNG infrastructure a good retirement investment? LNG pipeline companies offer several advantages for retirement portfolios: predictable “take or pay” contract structures, consistent dividend income, less technology risk than AI speculation, and participation in a massive infrastructure buildout. With US LNG export capacity set to grow 74% by 2032, these investments offer growth potential with more stability than pure tech plays. How do I know if I have too much risk in my portfolio? Many investors don’t realize their risk exposure until it’s too late. Warning signs include: heavy concentration in a few tech stocks, inability to explain what you own and why, portfolios that look identical to major indices, or having the same allocation today as you did 10 years ago despite nearing retirement. A personalized portfolio analysis from experienced portfolio managers can identify hidden risks. What’s the difference between working with Dupree Financial Group versus a large national firm? Instead of calling a 1-800 number and speaking with an assigned investment counselor who may have limited experience, you get direct access to portfolio managers with 47 years of investment experience. You’re working with a team of local financial advisors who know Kentucky’s economic landscape and can meet with you face-to-face. This personalized investment management approach means your portfolio is actively managed based on current conditions, not set-and-forget. Should I retire if I’m tired of my current job? Not necessarily. Retiring purely because you dislike your job, without adequate financial cushion, can create bigger problems. Consider the “Refire” alternative—transitioning to something you’re passionate about that still generates income. Many Dupree Financial Group clients have successfully launched second careers in construction, farming, consulting, or specialty crafts. This provides both financial security and life purpose. What does “if you don’t know what you own, you should” really mean? It means understanding not just the names of stocks in your portfolio, but why you own them, what risks they carry, how they generate returns, and whether they still fit your current life stage. Many investors can name their holdings but can’t explain the investment thesis or risk profile. Kentucky retirement planning requires this deeper understanding, especially as you transition from accumulation to preservation and income. How often should I review my retirement portfolio? In normal markets, quarterly reviews make sense. In volatile markets like we’re experiencing, more frequent check-ins help. However, this doesn’t mean constantly trading—it means ensuring your risk exposure matches your current needs and market conditions. Dupree Financial Group provides ongoing portfolio management, not annual check-ins followed by silence. Schedule Your Personalized Portfolio Analysis If you’re approaching retirement or already retired, now is the time to ensure your portfolio matches your risk tolerance and income needs. Don’t wait for a market correction to discover you’re overexposed to risk. Dupree Financial Group offers complimentary portfolio reviews where we’ll analyze: Your current risk exposure and whether it matches your life stage Hidden concentrations and correlation risks Income sustainability from your portfolio Opportunities you may be missing (like LNG infrastructure) Whether your current advisor is providing genuine value or generic advice Call us at 859-233-0400 or schedule directly on our website. Connect With Dupree Financial Group Personalized Portfolio Analysis: www.dupreefinancial.com Investment Philosophy & Team: www.dupreefinancial.com/about-us/ More Market Commentary & Podcasts: www.dupreefinancial.com/podcast Phone: 859-233-0400 The post Understanding Market Volatility and Strategic Retirement Investing in 2025 appeared first on Dupree Financial.

The Hidden Investment Risks Pre-Retirees and Retirees Don’t See Coming: Kentucky Retirement Planning Insights Are you approaching retirement and concerned about protecting your life savings from market volatility? In this comprehensive episode of the Tom Dupree Show, Kentucky retirement planning advisors Tom Dupree and Mike Johnson explore the multidimensional nature of investment risk and why personalized investment management is essential. 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 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. Key Takeaways: Investment Risk Management for Pre-Retirees Risk is multidimensional: Investment risk extends beyond simple volatility—it includes sequence of returns risk, concentration risk, and the risk of falling short of your retirement goals The Capital Asset Pricing Model misconception: More risk doesn’t automatically mean more return; it means a wider range of potential outcomes, both positive and negative The danger of false security: Long periods of strong returns can create complacency, causing investors to unknowingly take on excessive risk right before retirement Personalized portfolio analysis matters: Your investment strategy must align with your specific retirement timeline, income needs, and risk capacity—not just market averages Understanding beats panic: Clients who truly understand their portfolio holdings don’t panic during market downturns because they know their strategy is designed for their goals Active risk identification: Professional Kentucky retirement planning involves continuously identifying and monitoring specific risks to each holding, not just following the crowd Howard Marks on Investment Risk: Wisdom from a Market Legend 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. The Real-World Cost of Ignoring Investment Risk 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. Why Volatility Isn’t the Only Risk Pre-Retirees Face 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.” Additional Risk Dimensions for Kentucky Retirement Planning Falling short of goals: The risk that your portfolio won’t produce sufficient income for your desired retirement lifestyle Concentration risk: Over-exposure to single stocks or sectors, especially common with company stock or recent tech winners Unconventionality risk: The professional risk advisors take when thinking independently rather than following the crowd—but this can benefit clients long-term Underperformance risk: Short-term underperformance relative to indices, which requires conviction in your strategy and understanding your goals Hidden risk exposure: Unknown risks embedded in portfolios, particularly index funds that provide no true diversification strategy The False Sense of Security: Why Long Bull Markets Are Dangerous 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. Direct Access to Portfolio Managers: The Dupree Financial Difference 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: Deep understanding of your specific retirement timeline and goals Customized portfolio construction based on your unique risk capacity Ongoing education about what you own and why you own it Proactive risk identification specific to your holdings The ability to think unconventionally when it serves your interests “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. Why Index Funds Aren’t a Complete Investment Strategy 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: Your specific income needs in retirement Time horizon until you need to access funds Concentration risk in popular stocks or sectors The difference between the accumulation and distribution phases Tax efficiency of different investment approaches Building a Foundation: From Stocks to Portfolio 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. The Retirement Risk Equation: It’s About Income, Not Just Account Balance 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. Faith, Risk, and Investment Philosophy 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. Frequently Asked Questions About Investment Risk and Retirement Planning What is the biggest investment risk for pre-retirees? 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. How is investment risk different for retirees versus younger investors? 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.” Are index funds safe for retirement portfolios? 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. How much can I safely withdraw from my retirement portfolio annually? 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. Why should I work with a local Kentucky financial advisor instead of a large national firm? 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.” What does it mean to “know what you own” in my portfolio? 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. How often should I review my retirement portfolio risk? 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. What is concentration risk, and why does it matter? 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. How do I know if I’m taking too much risk before retirement? 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. What makes Dupree Financial Group’s investment philosophy different? 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. Schedule Your Complimentary Portfolio Risk Analysis 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: Identify hidden concentration risks in your current holdings Understand the sequence-of-returns risk as you approach retirement Evaluate whether your portfolio aligns with your retirement income needs Learn what you actually own and why it matters Develop a personalized strategy for your retirement timeline Call 859-233-0400 to schedule your complimentary consultation Or visit us online: Schedule Your Personalized Portfolio Analysis Learn About Our Investment Philosophy Listen to More Market Commentary Read Client Testimonials Explore Kentucky Retirement Planning Services Dupree Financial Group serves clients throughout Central Kentucky, including Lexington, Louisville, Frankfort, Winchester, Richmond, and surrounding communities. About the Tom Dupree Show 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 Share This Episode 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.

Bull Markets, Investor Hubris, and the Hidden Risks of Annuities Are you feeling smarter about your investments after years of strong market returns? In this episode of The Financial Hour of The Tom Dupree Show, Tom Dupree and Mike Johnson explore a critical truth that even legendary investors like Benjamin Graham learned the hard way: bull markets can create dangerous overconfidence. For those 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. Key Takeaways: Investment Lessons from Market History Bull Markets Create False Confidence: Even Benjamin Graham, Warren Buffett’s mentor, nearly lost everything after early success made him believe he “had Wall Street by the tail”—a lesson for today’s investors experiencing strong returns Market Success Often Includes Luck: Quick wins can lead to psychological distortions, especially when you’ve “unknowingly broken the rules of the game but won anyway” The Dangers of Autopilot Investing: Index funds and passive strategies mean following a “prescribed path that lots of other people are going,” with little thought given to how portfolios are composed Annuities Are Complex Insurance Products: Despite being marketed as simple solutions, annuities involve counterparty risk, surrender penalties, and fine print that rarely delivers promised returns Portfolio Transparency Is Powerful: Understanding exactly what you own—seeing individual stocks and bonds rather than packaged products—provides genuine comfort during market volatility Fear-Based Investing Creates Poor Outcomes: Investment decisions driven solely by fear (whether fear of loss or fear of missing out) typically underperform thoughtful, process-driven strategies The Benjamin Graham Story: When Success Breeds Dangerous Confidence 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.'” Why This Matters for Kentucky Retirement Planning Today 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. The Problem with “Autopilot” Investing: Index Funds and Groupthink 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.” The Windfall Effect: Why Unearned Money Often Gets Lost 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. Annuities: The “Simple Solution” That Rarely Delivers 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. Types of Annuities and Their Real-World Performance 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. The Hidden Risks Nobody Tells You About Annuities 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: Counterparty Risk: Who’s Really Backing Your Annuity? 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.” The Insurance Company Squeeze: When Spreads Get Tight 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.” The Commission Structure Nobody Mentions 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.” The Power of Portfolio Transparency: Seeing What You Actually Own 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: You know exactly which companies you own shares in You understand why each holding is in your portfolio You can see income generation in real-time, not theoretical returns You develop genuine comfort during market volatility because you know what you own You avoid the “black box” problem of packaged products 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.” Learning from Mistakes: The Value of Experience 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. The Critical Questions to Ask About Your Retirement Portfolio 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: “Do the numbers work for you at where they are?” “Do a critical analysis of what the investments are” “Is there an investment plan?” “Or is it—has it just been on autopilot and the autopilot’s taking you where you wanted to go?” “You need to reevaluate where things are today” 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?” Fear vs. Process: Making Better Investment Decisions 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. When Annuities Actually Make Sense (It’s Rare, But It Happens) 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.” Why “Simple Solutions” Rarely Work for Retirement 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: Index funds marketed as “set it and forget it” solutions Annuities sold as eliminating all market risk Any investment product that promises complexity has been eliminated Mass-market approaches that treat all investors identically 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. Ready to See What’s Really Under the Hood of Your Portfolio? 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: Honest assessment of your current portfolio’s strengths and vulnerabilities Analysis of whether you’re taking appropriate risks given your life stage Evaluation of any annuity contracts you currently own (unbiased review of actual terms) Direct conversation with experienced portfolio managers who personally manage client assets Clear explanation of what you own and why—no black boxes or packaged products Discussion of how to respect and protect the gains the market has provided 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. Frequently Asked Questions About Bull Markets, Annuities, and Retirement Investing What does it mean that “bull markets make you feel smarter than you really are”? 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. Why did Benjamin Graham nearly lose everything despite being Warren Buffett’s teacher? 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. What’s wrong with index fund investing for retirement? 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. How do index annuities actually work, and why do they underperform? 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. What is counterparty risk with annuities? 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. Are there situations where annuities make sense? 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. What does it mean to “look under the hood” of your portfolio? 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. Why is “autopilot” investing dangerous for those approaching retirement? 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. What should I do if I’ve benefited from recent strong market returns? 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. How do I know if fear is driving my investment decisions? 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. What’s the difference between fee-based advisors and commission-based annuity sales? 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. About The Financial Hour of The Tom Dupree Show 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.

Navigating Market Volatility: Why Income-Focused Investing Beats Speculation for Kentucky Retirement 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. Key Takeaways: Market Insights and Retirement Strategy Tech Sell-Off Context: The Dow dropped 794 points on Thursday as growth stocks pulled back from stretched valuations—a predictable correction in what Tom calls a “toppy market” Fed Rate Cut Expectations Shift: Market pricing for a December Fed rate cut moved from 95% probability to essentially a coin flip (50/50) in just days, affecting growth stock valuations Conservative Portfolios Outperform During Volatility: While the Nasdaq fell 4%, Dupree Financial Group’s dividend-focused, income-producing portfolio actually made money during the same period Flight to Quality Emerges: Investors moving toward healthcare, Berkshire Hathaway, and dividend-paying stocks as speculation cools Retirement Income Is Everything: Cash flow predictability matters more than price appreciation when you’re living off your investments 2026 Contribution Limits Announced: 401(k) increases to $24,500; IRAs to $7,500; new Roth catch-up rules for high earners Opportunities in Volatility: Dupree Financial Group added several positions in recent weeks, including quality names like Kroger Understanding the Recent Tech Sell-Off: What Happened and Why 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.” Why Growth Stocks Pulled Back 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. How Fed Rate Expectations Impact Growth Stocks 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.” The Interest Rate and Growth Stock Connection 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. Conservative Portfolio Performance: Making Money While Tech Falls 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 Dividend and Bond Foundation 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.” Flight to Quality: Where Smart Money Is Moving 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.” The Berkshire Hathaway Example 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. Technology’s Impact on Employment: The Verizon Example 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. 2026 Retirement Account Contribution Limits: What You Need to Know Mike provides timely information for retirement savers: “They just came out with the new contribution limits for 401(k)s and IRAs for 2026.” The New Numbers 401(k) Contribution Limit: Increased to $24,500 (up $1,000) IRA Contribution Limit: Increased to $7,500 Catch-Up Contributions Age 60-63: Even higher contribution allowed during this specific age window Important New Rule for High Earners 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.” Beyond the 401(k): Why You Need Additional Investment Strategies 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.” The In-Service Rollover Strategy 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. Retirement’s Real Risk: Running Out of Money vs. Running Out of Life 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.” The Purpose Question: What Are You Retiring To? 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. Why Retirement Is Inherently Risky (And How to Mitigate That Risk) 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. Finding Opportunities in Market Volatility 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.” The Kroger Purchase: Quality at Reasonable Prices 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: Buying quality companies during market weakness Investing in businesses that people actually use and understand Focusing on stable, dividend-paying companies rather than speculation Taking advantage of price volatility to acquire good businesses at better valuations 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. The Cornerstone of Retirement Portfolios: Predictable Income 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. Portfolio Transparency: Knowing What You Own and Why 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: Index funds where you own whatever 500 companies meet arbitrary criteria Target-date funds that Tom calls “zero in terms of creativity” Annuities backed by insurance company bond portfolios you never see Any “black box” product that obscures actual holdings 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. Market Outlook: Navigating Continued Choppiness 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. Ready to Understand What You Own During Market Volatility? 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: Honest assessment of how your current portfolio performed during recent volatility Analysis of whether your holdings are positioned for income production or just speculation Evaluation of 401(k) strategies, including in-service rollover opportunities Direct conversation with experienced portfolio managers who personally manage client assets during market ups and downs Clear explanation of what you would own and why—no index funds, no black boxes Discussion of how to find opportunities when others panic (like the April and recent pullbacks) Review of 2026 contribution limits and how to maximize tax-advantaged savings 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. Frequently Asked Questions About Market Volatility and Retirement Income Investing What caused the recent tech stock sell-off? 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. How did Dupree Financial Group’s portfolio perform during the tech sell-off? 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. Why do interest rates affect growth stock valuations? 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. What is a “flight to quality” in investing? 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. What are the 2026 retirement account contribution limits? 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. Can I move my 401(k) to an IRA while still working? 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. Should I use my 401(k) as my only retirement savings? 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. Why is income more important than growth for retirement portfolios? 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. What does it mean that retirement is “inherently risky”? 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.” Should I retire if I can afford to financially? 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. How do you find investment opportunities during market volatility? 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. Why does portfolio transparency matter during volatile markets? 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. About The Financial Hour of The Tom Dupree Show 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.

Three Essential Principles for Protecting Your Wealth in Today's Market Markets are at record highs again. If you've been diligently dollar-cost averaging into your 401(k) for years, watching your portfolio […] The post Three Essential Wealth Protection Principles from Psychology of Money | Dupree Financial Group appeared first on Dupree Financial.

Market Volatility and Strategic Bond Positioning: Why We're Preparing for What's Next Market Selloff Signals Valuation Concerns This week brought a stark reminder that what goes up doesn't always continue […] The post Market Volatility 2025: Why Strategic Bond Investment Can Protect Your Retirement | Dupree Financial appeared first on Dupree Financial.

Investment Planning for Retirement: Creating Income Streams Through Dividends Market Volatility and Your Retirement Plan: Why Income Matters This episode of the financial hour is from March 29, 2025 – […] The post Investment Planning for Retirement: Creating Income Streams Through Dividends appeared first on Dupree Financial.

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Understanding Market Volatility: What Kentucky Investors Need to Know Right Now When government shutdowns dominate headlines and market bubbles threaten portfolios, Central Kentucky investors need clear guidance from experienced financial […] The post Government Shutdowns, Market Bubbles, and Your Retirement Strategy appeared first on Dupree Financial.

Faith-Based Retirement Planning: How Personal Trials Shape Investment Wisdom with Kentucky Financial Advisor Tom Dupree Kentucky Financial Advisor Combines Faith and Finance In this episode of The Tom Dupree Show, […] The post Faith-Based Retirement Planning: How Personal Trials Shape Investment Wisdom with Kentucky Financial Advisor Tom Dupree appeared first on Dupree Financial.

AI Investment Bubble Warning: Why Compound Interest Beats Market Speculation for Kentucky Retirees Episode Length: 45 minutes | Host: Tom Dupree Jr. | Guest: Mike Johnson The current AI investment […] The post AI Investment Bubble Warning: Why Compound Interest Beats Market Speculation for Kentucky Retirees appeared first on Dupree Financial.

Building Wealth Through Boring Businesses: Why Mundane Investments Beat Glamorous Returns in Retirement Planning  The Secret to Retirement Wealth: Investing in Boring, Dividend-Paying Businesses Welcome to another episode of The […] The post  The Secret to Retirement Wealth: Investing in Boring, Dividend-Paying Businesses appeared first on Dupree Financial.

Understanding Value Investing Strategies and Market Valuations In this comprehensive episode of The Tom Dupree Show, experienced Kentucky financial advisor Tom Dupree and Mike Johnson explore the fundamental principles of […] The post Understanding Value Investing Strategies and Market Valuations appeared first on Dupree Financial.

The Psychology of Money: Warren Buffett's Compounding Returns Strategy and Retirement Planning Wisdom Understanding Compounding Returns: The Secret Behind Warren Buffett's $140 Billion Fortune In this episode of The Financial […] The post The Psychology of Money: Warren Buffett's Compounding Returns Strategy and Retirement Planning Wisdom appeared first on Dupree Financial.

Municipal Bond Fund Collapse: Why Direct Portfolio Management Protects Kentucky Retirement Plans When a municipal bond fund collapsed 50% in just two days, it sent shockwaves through the investment world […] The post Municipal Bond Fund Collapse: Why Direct Portfolio Management Protects Kentucky Retirement Plans appeared first on Dupree Financial.

Building Wealth Through Personalized Investment Management Building Generational Wealth: A Father-Son Perspective on Investment Management In this engaging episode of the Tom Dupree Show, local financial advisor Tom Dupree sits […] The post Building Wealth Through Personalized Investment Management – Tom Dupree Show appeared first on Dupree Financial.

Fed Rate Cuts 2025: AI Investment Opportunities and Duration Strategy for Kentucky Retirement Planning Federal Reserve Rate Cuts Signal Major Investment Opportunities Ahead In this episode of The Financial Hour, […] The post Fed Rate Cuts 2025: AI Investment Opportunities and Duration Strategy for Kentucky Retirement Planning appeared first on Dupree Financial.

Kentucky Retirement Planning: Your Complete Guide to Dividend Investing and Retirement Readiness Preparing for retirement requires more than just saving money—it demands a comprehensive strategy that addresses both your financial […] The post Kentucky Retirement Planning: Your Complete Guide to Dividend Investing and Retirement Readiness appeared first on Dupree Financial.

Investment Wisdom Through Literature: Faulkner's Lessons for Modern Kentucky Investors and Lexington's Economic Challenges Timeless Investment Principles Hidden in Classic Literature In this episode of the Tom Dupree Show, Kentucky […] The post Investment Wisdom Through Literature: Faulkner's Lessons for Modern Kentucky Investors and Lexington's Economic Challenges appeared first on Dupree Financial.

Why Your 401K Target Date Fund Could Be Sabotaging Your Retirement: A Financial Advisor's Guide to Better Planning Are you one of the millions of Americans unknowingly putting your retirement […] The post Why Your 401K Target Date Fund Could Be Sabotaging Your Retirement appeared first on Dupree Financial.

Financial Accountability Crisis: How Local Government Mismanagement Threatens Kentucky Retirement Planning Trust Principles and Financial Accountability in Uncertain Times In this episode of the Tom Dupree Show, Kentucky retirement planning […] The post Financial Accountability Crisis: How Local Government Mismanagement Threatens Kentucky Retirement Planning appeared first on Dupree Financial.

The Psychology of Money: Warren Buffett's Compounding Returns Strategy and Retirement Planning Wisdom Understanding Compounding Returns: The Secret Behind Warren Buffett's $140 Billion Fortune In this episode of The Financial […] The post The Psychology of Money: Warren Buffett's Compounding Returns Strategy and Retirement Planning Wisdom appeared first on Dupree Financial.

Why Tobacco Stocks and Alternative Investments Are Shaking Up Kentucky Retirement Planning Strategies In this episode of The Financial Hour, Kentucky retirement planning strategists Tom Dupree and Mike Johnson discuss […] The post Why Tobacco Stocks and Alternative Investments Are Shaking Up Kentucky Retirement Planning Strategies appeared first on Dupree Financial.

How Trump's Trade Policy Reform is Rebuilding American Manufacturing Jobs and Strengthening Economic Security America's economic landscape is undergoing a historic transformation through strategic trade policy reform that prioritizes American […] The post How Trump's Trade Policy Reform is Rebuilding American Manufacturing Jobs and Strengthening Economic Security appeared first on Dupree Financial.

AI Investment Strategies vs. Traditional Portfolio Management: A Kentucky Financial Advisor's Perspective Are you wondering whether AI investment strategies belong in your retirement portfolio? In this episode of The Financial […] The post AI Investment Strategies vs. Traditional Portfolio Management: A Kentucky Financial Advisor's Perspective 8-02-05 appeared first on Dupree Financial.

Investment Opportunities in New York: A Contrarian's Guide to Regional Economic Recovery Uncovering Hidden Investment Opportunities Through Regional Economic Analysis In this episode of the Tom Dupree Show, investment strategist […] The post Investment Opportunities in New York: A Contrarian's Guide to Regional Economic Recovery8-02-25 appeared first on Dupree Financial.

Building Wealth Through Personalized Investment Management Building Generational Wealth: A Father-Son Perspective on Investment Management In this engaging episode of the Tom Dupree Show, local financial advisor Tom Dupree sits […] The post Building Wealth Through Personalized Investment Management – Tom Dupree Show appeared first on Dupree Financial.

Investment Wisdom Through Literature: Faulkner's Lessons for Modern Kentucky Investors and Lexington's Economic Challenges Timeless Investment Principles Hidden in Classic Literature In this episode of the Tom Dupree Show, Kentucky […] The post Investment Wisdom Through Literature: Faulkner's Lessons for Modern Kentucky Investors and Lexington's Economic Challenges appeared first on Dupree Financial.

Kentucky Retirement Planning: Why You Need to Know What You Own Episode Air Date: July 19, 2025 The Hidden Dangers of One-Size-Fits-All Retirement Portfolios Are you approaching retirement with a […] The post Kentucky Retirement Planning: Why You Need to Know What You Own appeared first on Dupree Financial.

Biblical Wisdom for Investment Planning and Health Policy Changes Are you facing unexpected financial challenges or wondering how recent health policy changes might affect your investment portfolio? In this episode […] The post Biblical Wisdom for Investment Planning and Health Policy Changes appeared first on Dupree Financial.

Market Highs and Retirement Planning: Essential Investment Strategies for Pre-Retirees in Lexington, KY Are you a pre-retiree in Lexington, KY, approaching retirement while markets sit at historic highs? In this […] The post Market Highs and Retirement Planning: Essential Investment Strategies for Pre-Retirees in Lexington, KY appeared first on Dupree Financial.

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Why Your 401K Target Date Fund Could Be Sabotaging Your Retirement: A Financial Advisor's Guide to Better Planning Are you one of the millions of Americans unknowingly putting your retirement […] The post Why Your 401K Target Date Fund Could Be Sabotaging Your Retirement appeared first on Dupree Financial.

In this episode of The Tom Dupree Show, financial advisor and host Tom Dupree delivers incisive political commentary while weaving in essential financial wisdom for investors. Broadcasting from Dupree Financial […] The post Political Commentary and Financial Insights: Federal Holidays, Historical Literacy, and Investment Strategy appeared first on Dupree Financial.

Why Smart Retirement Investors Are Looking at Energy Stocks in 2025 The energy sector has been dramatically undervalued by the market, creating compelling opportunities for retirement investors seeking dividend income […] The post Energy Stocks for Retirement: Why Oil Investment Strategy Makes Sense in the AI Era appeared first on Dupree Financial.

Dividend Investing for Retirement Income: How to Build Wealth Outpacing Inflation Introduction In this episode of The Financial Hour, Registered Investment Advisor Tom Dupree reveals how dividend investing for retirement […] The post Why Dividend Investing Beats Inflation for Retirement Planning appeared first on Dupree Financial.

Government Waste, Biblical Wisdom, and Local Accountability: Lessons for Pre-Retirees in Uncertain Times Originally aired June 7, 2025 Understanding True Change: Why Most People Never Repent Tom draws powerful parallels […] The post Government Waste, Biblical Wisdom, and Local Accountability: Lessons for Pre-Retirees in Uncertain Times appeared first on Dupree Financial.

Investment Psychology and Market Timing: Why Pre-Retirees Need a Long-Term Strategy During Market Volatility The financial markets can feel like an emotional rollercoaster, especially for pre-retirees and retirees who see […] The post Market Psychology and Investment Timing: Essential Insights for Pre-Retirees and Retirees appeared first on Dupree Financial.

Why Government Spending and Personal Values Are Connected: Biblical Wisdom for Financial and Political Reform Introduction In this thought-provoking episode of The Tom Dupree Show, financial advisor Tom Dupree draws […] The post Why Government Spending and Personal Values Are Connected appeared first on Dupree Financial.

Overcoming Investment Complacency: How to Build a Retirement Portfolio That Works in Uncertain Markets Introduction Two months after the market's April 2025 bottom, investor complacency is already setting in. On […] The post Overcoming Investment Complacency: How to Build a Retirement Portfolio That Works in Uncertain Markets appeared first on Dupree Financial.

South African Political Crisis and Financial Policy Lessons: Understanding Global Economic Instability In this episode of The Tom Dupree Show, host Tom Dupree Jr. examines the ongoing political and economic […] The post South African Political Crisis and Financial Policy Lessons: Understanding Global Economic Instability appeared first on Dupree Financial.

Building Wealth Through Boring Businesses: Why Mundane Investments Beat Glamorous Returns in Retirement Planning  The Secret to Retirement Wealth: Investing in Boring, Dividend-Paying Businesses Welcome to another episode of The […] The post  The Secret to Retirement Wealth: Investing in Boring, Dividend-Paying Businesses appeared first on Dupree Financial.

Illegal Immigration and Law Enforcement Crisis: The Impact of Sanctuary Cities Episode Overview: America's Immigration Enforcement Crisis In this episode of The Tom Dupree Show, host Tom Dupree addresses the […] The post Illegal Immigration and Law Enforcement Crisis: The Impact of Sanctuary Cities appeared first on Dupree Financial.

Market Recovery and Investment Strategy: Tips from The Financial Hour The Market's Recent Recovery and Investment Opportunities In this episode of The Financial Hour, Tom Dupree and Mike Johnson discuss […] The post Market Recovery and Investment Strategy: Tips from The Financial Hour appeared first on Dupree Financial.

School Budget Concerns and Local Politics: Tom Dupree Tackles Fayette County Issues Introduction In this week's episode of The Tom Dupree Show, host Tom Dupree discusses pressing local issues affecting […] The post School Budget Concerns and Local Politics: Tom Dupree Talks Fayette County Issues appeared first on Dupree Financial.

Investment Planning for Retirement: Creating Income Streams Through Dividends Market Volatility and Your Retirement Plan: Why Income Matters In today's unpredictable market environment, having a clear investment plan is more […] The post Investment Planning for Retirement: Creating Income Streams Through Dividends appeared first on Dupree Financial.

Harvard's Financial Crisis: Could Tax-Exempt Status Loss Mirror Solomon Brothers' Demise?  Harvard University's ongoing battle with the federal government over research grants, tax-exempt status, and what it means for higher […] The post Could Harvard's Tax-Exempt Status Loss Mirror Solomon Brothers' Demise? appeared first on Dupree Financial.