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.

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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:

1. Serve retirement investors who might not get attention from large brokerage firms
2. Maintain local presence and accountability in Lexington, Kentucky
3. Provide team-based service rather than single-advisor relationships
4. Focus on income and risk mitigation rather than index performance
5. Conduct independent research and select individual investments
6. Build long-term relationships rather than pursuing transactions
7. 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.”

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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.

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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.

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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.