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September 6, 2025 44 mins

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 down with his son James to discuss Kentucky retirement planning, personalized investment management, and the evolution of investing over the past four decades. This conversation offers valuable insights for both young investors starting their wealth-building journey and pre-retirees seeking direct access to portfolio managers who understand their unique financial goals.

Tom Dupree, founder of Dupree Financial Group, brings decades of experience in fee-based retirement investing, while James provides a millennial perspective on modern investment tools and strategies. Together, they explore the fundamental differences between their personalized investment management approach and mass-market investment firms.

The Evolution of Investment Accessibility and Financial Literacy

The investment landscape has transformed dramatically since Tom began his career at age 21. Where investors once paid 5% commissions through traditional stockbrokers, today’s platforms like Robinhood have democratized market access. However, this accessibility doesn’t automatically translate to financial success.

Key insights from the discussion:

  • Modern investors have unprecedented access to information and low-cost trading platforms
  • Many young adults remain financially illiterate despite having powerful investment tools at their disposal
  • Women, particularly younger women, represent an underserved demographic in investment education
  • The fundamentals of wealth building remain unchanged: discipline, consistency, and long-term thinking

“The average person has a lot more access to information about financial matters if they’re willing to study it and try to learn about it.” – Tom Dupree

Fundamental Analysis vs. Momentum Investing: The Dupree Approach

What sets personalized investment management apart from algorithmic or momentum-based strategies? The Duprees emphasize the importance of understanding the companies behind the stocks, not just following market trends.

Direct Company Research and Analysis

James discusses his role in booking meetings with companies in their portfolio – a hands-on approach that exemplifies their commitment to fundamental analysis investing:

“We’re directly talking to these companies, doing our own research. Some other companies may not do that and they’ll invest in a stock just because it has momentum… they’re not really looking at the fundamentals of the company.”

The Importance of Technical Analysis

While fundamental analysis drives long-term investment decisions, technical analysis helps optimize entry and exit points:

  • Short-term decisions: Technical analysis helps identify optimal buying opportunities
  • Long-term strategy: Fundamental analysis ensures sound company selection
  • Market mechanics: Understanding buyer/seller dynamics drives price movement
  • Risk management: Combining both approaches provides a comprehensive investment strategy

Wealth Building Strate

Mark as Played

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