THE TOM DUPREE SHOW | PODCAST SHOW NOTES
When to Hold, When to Sell: Staying Invested Through Market Volatility
The Tom Dupree Show | Dupree Financial Group | dupreefinancial.com | 859-233-0400
Episode Description
When markets get choppy, the instinct to move to the sidelines can feel overwhelming — but acting on that instinct often costs investors far more than the volatility itself. In this episode, Tom Dupree and Lead Advisor Mike Johnson walk through the discipline behind staying invested, explaining how Dupree Financial Group evaluates when to hold a position, when to trim, and when to walk away entirely.
The conversation covers real examples from their current portfolio — including dividend-paying holdings, pipeline stocks, and a diesel engine company that became a quasi-AI play — to illustrate how valuation and income generation shape every buy, hold, and sell decision. Tom and Mike also explain why the firm carries a significant cash position right now, and what that signals about how they view current market valuations.
“Income from the portfolio tilts the table in your favor — it puts time back on your side while you wait for price appreciation.”
Topics Covered
- Why panic selling during volatility almost always harms long-term returns
- How dividend income changes the calculus on whether to hold or sell
- The difference between timing the market and assessing individual stock valuations
- Real portfolio decisions: oil companies, pipeline stocks, Kroger, and an AI-adjacent diesel play
- Why the firm is holding more cash than usual — and what it says about current valuations
- The perma-bull vs. perma-bear debate and why optimism is essential for long-term investors
- How a team-based investment approach produces better decisions than any single viewpoint
- Why most 401(k) holders don’t know what they own — and why that matters more than ever
Key Takeaways
- Dividends give you staying power. When a holding generates consistent income, missing that payout by selling too early is a real cost. Income from your portfolio buys you time to wait out price swings without being forced to sell at the wrong moment.
- The market’s best days cluster around its worst ones. Nearly half of the 50 best market days over the past 30 years occurred during bear markets. Investors who exit to avoid the drops frequently miss the recoveries that follow within days.
- Valuation — not emotion — should drive selling decisions. Tom and Mike trim positions when the math no longer makes sense: oil company stocks trading 25% above where they were when oil prices were identical, or a grocery chain whose core margin driver is eroding. Logic, not fear, triggers the sell.
- You can’t time the market, but you can prepare for it. As investor Howard Marks has noted, the goal isn’t prediction — it’s preparation. Knowing what you own, why you own it, and at what price it becomes expensive puts you in a position to act with clarity rather than react with panic.
- Not all stocks are meant to be held forever. Some positions are designed to be traded; others are core long-term holds. Understanding the difference — and building that distinction into your process from the start — is what separates disciplined investing from guesswork.
- A cash position is itself a valuation statement. Dupree Financial Group currently holds a significant cash and bond allocation because valuations look stretched. That defensive posture has allowed the portfolio to perform comparably to fully-invested indexes while taking on meaningfully less risk.
- Know what you own. Many retirement investors hold mutual funds or target-date funds without understanding the underlying holdings. If price movements in your portfolio are a mystery to you, you’re letting emotions — not analysis — make your decisions for you.
About The Tom Dupree Show
The Tom Dupree Show is hosted by Tom Dupree, founder of Dupree Financial Group and a 47-year veteran of the investment business. Each episode covers the financial topics that matter most to retirees and those approaching retirement — in plain English, without the Wall Street spin.
Dupree Financial Group is a fee-only, fiduciary Registered Investment Advisory firm based in Lexington, Kentucky. The firm manages separately managed accounts focused on income-generating, dividend-paying portfolios — no products sold, no commissions, no conflicts of interest.
Past episodes are available at dupreefinancial.com under the podcast tab.
Schedule a Complimentary Portfolio Review
If you’re not sure whether your portfolio is built to generate income through market volatility — we’ll take a look. No charge. No pressure. Just an honest conversation about what you own and whether it’s working for you.
Call: 859-233-0400 | Visit: dupreefinancial.com
Dupree Financial Group is an SEC-registered investment adviser. Registration does not imply a certain level of skill or training. The information presented is for educational purposes only and does not constitute investment advice. All investing involves risk, including the possible loss of principal. Past performance is not indicative of future results. Securities mentioned are for illustrative purposes only and are not a recommendation to buy or sell. Please consult a qualified financial professional before making any investment decisions.
Dupree Financial Group is a Registered Investment Advisor (RIA) registered with the Securities and Exchange Commission. Registration does not imply a certain level of skill or training. The information presented on this program is for educational purposes only and does not constitute investment advice, a solicitation, or a recommendation to buy or sell any security. Investing involves risk, including the potential loss of principal. Past performance is not indicative of future results. Please consult with a qualified financial advisor before making any investment decisions.