Mailbag! Maximizing Dividends, Spending in Retirement, Managing a 529

In this episode of Motley Fool Hidden Gems Investing, Motley Fool personal finance expert Robert Brokamp is joined by Motley Fool contributor Dan Caplinger to answer financial planning questions sent in from listeners, including: How do ETFs affect the recommendation to own 25 to 50 stocks? How can a new retiree switch from saving to spending after decades of frugality? Since stock prices drop after a dividend payment, is it a "nothing-burger"? How to manage a 529 as a kid gets ready to go to college? Should you automatically reinvest dividends or use the cash to invest in something else? What to do when you're getting a late start on saving for retirement? To catch full episodes of all The Motley Fool's free podcasts, check out our podcast center. When you're ready to invest, check out this top 10 list of stocks to buy. Missed Nvidia in 2009? This Rare Signal Is Flashing Again. In 2009, a "Double Down" signal flashed for a little-known chipmaker called Nvidia. For the first time in years, that same "Total Conviction" signal is flashing for a company 1/100th the size of Nvidia. Continue » In 2009, a "Double Down" signal flashed for a little-known chipmaker called Nvidia. If you'd invested $5,000 then, you'd be sitting on $2,499,895 today.* Now, for the first time in years, that same "Total Conviction" signal is flashing for a company 1/100th the size of Nvidia. It's a key player in the $1.8 trillion space race, and with the stock recently sitting 20% off its highs, the window to get in early is closing fast. *Stock Advisor returns as of June 29, 2026 This podcast was recorded on June 20, 2026. Robert Brokamp: Merry Weekend, Fools, and welcome to the first Mailbag episode of the Personal Finance Edition of the Motley Fool Hidden Gems Investing Podcast. I'm Robert Brokamp, though my nickname around The Fool is "Bro," which you'll hear about today. My colleagues who host the weekday shows have been soliciting questions from our audience for the past few months. As it turns out, y'all have plenty of financial planning questions. I finally devote an entire episode to answering some of them, and to help me as my longtime partner in crime, Dan Caplinger. Dan is a former financial planner and trust attorney. For more than six years, Dan and I have been answering questions for Motley Fool Premium members during two live shows each and every week. I asked Dan to join me for this inaugural Mailbag episode. Welcome to the show, Dan. Dan Caplinger: Glad to be here, bro. It's always fun to talk financial planning with. Robert Brokamp: Outstanding. This is how this is going to work. We chose six questions from those that we received, which touch on personal finance, as well as a little bit of investing. I will read each question, and Dan and I will take turns taking a first crack at it, and then the other will add his thoughts if he has any. With all that said, here's the first question. It comes from brother Zach, who wrote in that The Fool recommends holding at least 25 individual stocks. How do ETFs play into that? Do they count as one stock, 1.5 stocks, or do you count them as completely outside of the 25 individual holdings? Dan, what do you think? Dan Caplinger: Zach, I need to update you quickly on The Fool philosophy because Fool CEO co-founder Tom Gardner recently updated that 25 individual stock number to 50. That really reflects the importance of you have so many individual stocks that overlap in terms of industry, in terms of business model. You don't want to assume that just having 25 stocks is going to give you perfect diversification. That's part of the justification for Tom pushing that number up to 50. I wanted to get that out of the way first. But answer the question you asked: how do you deal with exchange-traded funds? For me, an ETF counts as however many stocks that fund has a significant position in. Let's take a couple of examples. A lot of people invest in ETFs that track the S&P 500 index. To me, if you have that one ETF as a position, then you have satisfied the 50-stock requirement. You have a diversified portfolio. I am comfortable with people. If you don't like investing in individual stocks, just picking a broad market ETF like that can get the job done. But not all ETFs are like that. Some ETFs are more concentrated. I know one popular ETF that concentrates on South Korean stocks, it really has two positions. Two positions make up half of the entire portfolio. To me, that's not a diversified portfolio. That ETF counts really closer to just like two stocks for me. You have to look at the holdings and make a judgment call. Robert Brokamp: I think it's important to keep in mind the spirit of this rule. The guidance is so that you don't have too much writing on one stock or one type of stock, but also that you have enough exposure to other types of stocks, industries and sectors. When I look at my portfolio, which is a mix of individual stocks at ETS and mutual funds, I use Mo

Mailbag! Maximizing Dividends, Spending in Retirement, Managing a 529

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