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

Summary

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Motley Fool Hidden Gems Investing – Mailbag! Maximizing Dividends, Spending in Retirement, Managing a 529

Date: June 20, 2026
Host: Robert Brokamp (“Bro”)
Guest: Dan Kaplinger
Episode Theme:
The first dedicated “Mailbag” episode for the podcast’s personal finance edition, Bro and Dan answer real listener questions on a variety of personal finance and investing topics. The episode is practical and relatable, with seasoned advice shaped by decades of experience.

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Overview

This episode dives into listener question topics ranging from portfolio diversification, switching from saving to spending in retirement, understanding dividends and 529 college savings drawdowns, to retirement planning for late starters. Dan Kaplinger, a longtime financial planning partner of Bro’s, joins for his expertise. The episode is casual, supportive, and information-rich, with actionable advice for investors at all life stages.

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Key Discussion Points & Insights

1. ETFs in Portfolio Diversification (00:56–04:14)

• Listener Question: Should you count an ETF as one “stock” for diversification, or should it count based on its holdings?
• Dan’s Take:
  • The Motley Fool recently increased diversification guidance from 25 to 50 individual stocks.
  • “If you have that one ETF as a position, then you have satisfied the 50 stock requirement—if it tracks the S&P 500.” (B, 02:07)
  • Not all ETFs are equally diversified—some are highly concentrated and shouldn’t be counted the same as a broad market ETF.
• Bro’s Additions:
  • Focus on the “spirit” of diversification—ensure you don’t have big overlaps across holdings.
  • Tools like Morningstar’s X-Ray can show your true exposure across accounts.

2. Mindset Shift: Spending in Retirement (04:14–07:19)

• Listener Matt: Saved a few million dollars despite a modest income but struggles to shift from saving to spending.
• Bro’s Advice:
  • “You could feel more comfortable spending a little bit of your money… try a very conservative guideline such as the old 4% rule. For someone who’s 70, even 4% is quite safe.” (A, 04:45)
  • Consider withdrawal order: taxable accounts first, then traditional IRAs, lastly Roth—though at age 73, RMDs (required minimum distributions) begin.
  • “You might value having that objective second opinion [from an advisor] where someone says, listen, you can feel very, very, very comfortable spending this amount each and every year.” (A, 05:54)
• Dan’s Encouragement:
  • If you’re used to modest spending, try “trial upgrades”—nicer hotels, business class flights: “See if those ways to spend your money have value to you… You deserve those little luxuries as you enter your golden year.” (B, 06:36)

3. Dividends: Are They a “Nothing Burger”? (07:50–10:51)

• Listener Kasey: Wonders if dividend payments matter, since stock prices drop by the dividend amount.
• Dan Explains:
  • “You’re not going to get money that way because you're absolutely right. The share price usually will adjust downward to reflect the dividend…” (B, 08:38)
  • Over time, price appreciation comes from business growth—dividends reflect the business’s ability to generate income.
  • Retirees may prefer dividend payments for psychological comfort, but selling shares can serve the same function.
  • On short-term bond ETFs: “It’s not a nothing burger, it’s really the whole burger. It’s the entire point because that’s the income those assets generate throughout the month.” (B, 10:14)
• Bro’s Analogy:
  • Think of stocks and bonds as “temporary cash holder(s)”—dividends/interest pass through to you, and dividend growth historically outpaces inflation.

4. Best Practices for Drawing Down a 529 College Savings Plan (10:51–15:20)

• Listener Bonnie: Two sons, one 529 account nearly enough for tuition, asks best drawdown strategies.
• Bro’s Strategy:
  • As college approaches, move 529 to cash to avoid risk of a market drop interfering with tuition needs.
  • Payments for tuition/fees can go directly to the school, other qualified expenses (books, off-campus housing) reimburse to you—save receipts.
  • Noticeable reductions in household expenses with child at college may offset part of the cost.
• Dan’s Tips:
  • Match 529 withdrawals to the year of the qualifying expense—IRS rules are strict.
  • Age-based portfolios in 529 plans may handle de-risking automatically.
  • If you have multiple kids, consider the “family 529 strategy”—leftover funds can be transferred between siblings, affecting how conservatively you invest each account.

5. Dividend Reinvestment: Automatic or Manual? (16:47–18:39)

• Listener Zach: Reinvest dividends automatically or take the cash?
• Dan’s Preferences:
  • Depends on conviction about the stock and investment timeframe.
  • For taxable accounts, Dan prefers not to reinvest, citing complicated tax accounting: “I like it when those purchases in taxable accounts are cleaner.” (B, 17:40)
  • In retirement accounts (IRAs, 401ks), reinvestment is fine—no tax impact.
• Bro’s Portfolio Management Tip:
  • You can use cash dividends to rebalance overweight positions or gradually de-risk as you approach retirement.
  • “Once I’m within five years of retirement, I’ll probably stop reinvesting, let the cash build and maybe shift it to bonds.” (A, 18:29)

6. Starting Late: Building a Retirement Plan Without an Employer Plan (18:39–22:56)

• Listener Bill: Age 44, just starting, $70k in savings, no workplace retirement plan, wants to catch up.
• Bro’s Recommendations:
  • You’re behind but not hopeless—having an emergency fund and savings is a strong foundation.
  • If W2 employee: Open an IRA (limit $7,500/year for 2026).
  • If self-employed: Consider a solo 401(k) for higher annual contribution limits.
  • If funds aren’t needed for the next five years, invest them in equities for higher growth potential.
  • Diversify with broad ETFs, learn about individual stocks over time.
  • Consider working longer to maximize savings and Social Security—delaying claiming increases your benefit.
  • “Aim to find something you’ll be happy to do well into the second half of your 60s.” (A, 21:44)
• Dan’s Addendum:
  • “Don’t be afraid to invest for retirement in a regular taxable brokerage account… growth stocks that don’t pay dividends for the most part… can be a tax-efficient way to get your money working.” (B, 22:21)

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Notable Quotes & Memorable Moments

• Dan: "If you have that one ETF as a position, then you have satisfied the 50 stock requirement." (02:07)
• Bro: “The guidance is so that you don’t have too much riding on one stock, or one type of stock, but also that you have enough exposure to other types of stocks, industries, and sectors.” (03:13)
• Bro (to retirees struggling to spend): “You can feel very, very, very comfortable spending this amount each and every year and you’re not going to run out of money.” (05:54)
• Dan (on treating yourself in retirement): “You deserve those little luxuries as you enter your golden years.” (06:36)
• Dan (on dividends): “It’s not a nothing burger, it’s really the whole burger. It’s the entire point.” (10:14)
• Bro (on 529 drawdown): “Once my kids were in high school, I played it very safe with the 529s. So I put them all in cash. That’s pretty conservative.” (11:20)
• Dan (on dividend reinvestment in taxable accounts): “It makes my tax accounting harder whenever I close out that position.” (17:40)
• Bro (on later-in-life retirement prep): “One of the most powerful things you could do is just work a bit longer. That allows you to save more, to delay withdrawing on your savings and to delay claiming Social Security.” (21:27)
• Dan (summed up): “Don’t be afraid to invest for retirement in a regular taxable brokerage account.” (22:21)

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Timestamps for Key Segments

• 00:56: How do ETFs count for diversification?
• 04:14: Transitioning from saver to spender in retirement; withdrawal order
• 07:50: Dividend payments and portfolio returns
• 10:51: Best strategies for drawing down a 529 college plan
• 16:47: Should you reinvest dividends or take cash?
• 18:39: Retirement planning for late starters without an employer plan
• 22:56: Episode wrap-up

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This episode is brimming with practical, empathetic financial wisdom—the ideal listen (or read!) for investors looking for answers at any stage of their journey.

Transcript

[A]

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. And my colleagues who host the weekday shows have been soliciting questions from our audience for the past few months. And it turns out y' all have plenty of financial planning questions. So I thought I'd devote an entire episode to answering some of them. And to help me is my longtime partner in crime, Dan Kaplinger. Dan is a former financial planner and trust attorney, and 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. So I asked Dan to join me for this inaugural mailbag episode. Welcome to the show, Dan.

[B]

Glad to be here, bro. It's always fun to talk financial planning with you.

[A]

Outstanding. So this is how this is going to work. So 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, one and a half stocks, or do you count them as completely outside of the 25 individual holdings? Dan, what do you think?

[B]

So, Zach, I need to update you quickly on the full philosophy because Fool CEO co founder Tom Gardner recently updated that 25 individual stock number to 50. That that really reflects the importance of you have so many individual stocks that kind of 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. So I wanted to get that out of the way first. But to answer the question you ask, how do you deal with exchange traded funds? For me, an ETF counts as however many stocks that fund has a significant position in. So let's take a couple of examples. A lot of people invest in ETFs that track the S&P 500 index. And 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. So to me, that's not a diversified portfolio. That ETF counts really closer to just like two stocks for me. And so you kind of have to look at the holdings and make a judgment call.

[A]

Yeah. And I think it's important to keep in mind the spirit of this rule. Right. The guidance is so that you don't have too much riding on one stock or one type of stock, but also that you have enough exposure to other types of stocks, industries, and sectors. So when I look at my portfolio, which is a mix of individual stocks and ETFs and mutual funds, I use Morningstar's X ray tool to look at how my portfolio is actually allocated, because that tool can look into the mutual funds at ETS and see which stocks or investments it holds. And so I know, you know, when you add my individual holding in Berkshire to my S&P 500 index fund to whatever actively managed funds I have that have Berkshire, this is the total amount I have in that stock. And, you know, you could have all kinds of ETFs, but you have. You're not really diversified because there's so much overlap. So I think that's also important to keep in mind.

[B]

That's a really smart thing to do because these days, Even big market ETFs more concentrated than they were in the past. And so getting some kind of tool that gives you that X ray gives you that look through can be really valuable.

[A]

All right, let's get to our second question from Matt. So I've been reading the fool and Investing foolishly for about 30 years. My wife and I have lived a good, though not extravagant life. While I have never made more than $50,000 per year, we have grown our portfolio to a few million dollars, as well as owning a home that is worth more than a million dollars. And we have gold and other assets all debt free. Wow, that's outstanding, Matt. Now I am 70 and retired. Our Social Security dividends and other income beat all of our expenses. I'm having a hard time switching mindsets from saving mode to spending mode. I can't seem to bring myself to sell shares and withdraw the funds from the portfolios. What advice do you have for new retirees who need to switch from Saving mode to drawdown mode. And which accounts from among the ira, Roth, sep, joint and personal should we draw down first? Thanks to the fool for a lifetime of sound investment advice. Well, congratulations. You have done a fantastic job. You know, not knowing everything about your situation, but it sounds like you're in fantastic shape. So congratulations to you and you probably could feel more comfortable spending a little bit of your money. Just a couple of thoughts. You might want to choose just a really conservative guideline such as the old 4% rule. I've talked on the show before about how 4% is actually probably too low, should be closer to 5% and that's for someone who's 65. So if you at a 70 year old withdrew 4%, that's pretty safe. And very soon you're going to be required to take some money out anyhow, at least from your traditional accounts because at age 73 you're going to have to start taking required minimum distributions from your traditional accounts so you could at least feel comfortable spending that money. Which brings us to the question of the order of withdrawals. So the basic rule that you often hear is that you draw down your taxable accounts first, then traditional accounts and then the Roth accounts. But since you're near your RMD age, you actually might start with the traditional accounts first. And one other thing, I'll just add that if you work with or have considered working with a financial planner, this is a great question for her or him, you might value having that objective second opinion where someone looks at everything and says, listen, you can feel very, very, very comfortable spending this amount each and every year and you're not going to run out of money. Dan, what do you think?

[B]

The other thing I'll just point out is you talk about having had a modest lifestyle throughout your career. And if you are comfortable, if you don't have aspirations to spend a whole bunch of extra money, then you might be in a position you're totally comfortable maintaining that lifestyle. You're not necessarily looking to spend a whole bunch more money. But here's the thing that you might consider Try out some upgrades. If you stay at a certain type of hotel, consider moving to the next upgrade up. If you routinely fly coach, then consider trying a business class flight. Just try looking at some of those ways to spend your money and see if they have value. Some of them won't, but some of them will. That might give put you in a position, you're more comfortable spending that money you've worked so hard to accumulate and that you've done such a good job investing. You deserve those little luxuries as you enter your golden year.

[A]

Very well said. Foreign.

[C]

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[A]

Bettertakeaction.org let's move on to question number three from Kasey. When stocks pay dividends, technically their share price drops by the exact amount to offset that since it's coming off their books. So you would have to hope for share price appreciation to come out ahead. Correct. Retirees love dividend stocks because it gives them income. Technically, a non dividend stock could give them income as well by selling the exact same amount of stock each time to create a dividend yourself minus the different tax treatments. And with a Bond ETF like the iShares 0 to 3 month Treasury Bond ETF ticker sGov, that doesn't get much share price appreciation. Isn't the dividend payment every month kind of a nothing burger? Because you aren't getting share price appreciation with that, so you're just breaking even. Dan, what do you say?

[B]

Yeah. So Kasey, you're right. You can't just get rich by buying the stock the day before the ex dividend date and then selling it right after collecting the dividend and then selling the stock. You're not going to get money that way because you're absolutely right. The share price usually will adjust downward to reflect the dividend that's going to get paid out. However, that's just looking at one day in time over a longer period of time. Ideally, the company is being financially successful, the stock price is rising over time. And in part, some of that is because of the income producing power that that business has. That business is generating income, that cash flow is coming in, the assets of the business are going up, the share price is going up. In line with that, it's exactly some of those assets that are going to pay your dividend. So it's not just that there's share price appreciation just from, I don't know, multiple expansion or investor demand or things like that is because the business is operating that way now. Also your point, it is true, shifting to dividend stocks in retirement just for the cash flow purpose. It's not necessary. You can just sell shares periodically as you point out, it's just a comfort thing. A lot of people are more comfortable leaving their shares intact, not selling in retirement. They feel like they are selling off their principal if they sell shares. Whereas a dividend payment, it's just income, it's not selling principal off, it's maintaining the income producing potential of the portfolio. One last thing you'll notice with that ETF that you're talking about, if you look at the share price trends, often the ETF will pick up like a penny a day and it'll keep doing that penny a day. At the end of the month it takes all those pennies, it pays them all out in a dividend. And so you can kind of see it, that makes the dividend payment. It's not a nothing burger, it's really the whole burger. It's the entire point because that's the income that, that, that those assets are generating throughout the month.

[A]

Yeah, I always think about this as you could think of like a dividend paying stock or a bond fund as sort of a temporary cash holder. Right? Cash comes into it with the dividend paying stock. It's, you know, basically the earnings from the company. It holds that cash for a while and then it gives it to you as the holder of the stock. And same with the bond fund, except that cash is coming from the interest paid from the bonds and then eventually it gets distributed to you. One of the differences though, with the dividend paying stock, ideally the dividend is growing year after year, if not quarter after quarter. Historically, dividends have outpaced inflation by about 1 to 2 percentage of points. So that's part of why the stock price rises, because investors are anticipating bigger dividends. But in the end, you're still ending up getting that cash. It's definitely not a nothing burger. All right, let's go on to question number four from Bonnie. Over 10 years ago, I started contributing to a 529 for both of my sons. My oldest son is now a senior in high school and looking to decide on a university in the next week or so. So it's a very exciting time for us as I look at his two options. When school is in state and we would be able to cover the four years of tuition and board with what is currently in his 529. However, the other school is out of state and it'll take a bit more than what is in the 529. In all the years I've been listening to the Motley fool podcast and it's been many, I've never heard anyone cover the best ways to draw down a 529. I'm sure that there are a few strategies and I'm curious to know the pros and cons associated with each. Any chance Robert Brokamp could opine on the topic in the near future? Well, Bonnie, I think there's a very good chance because we're going to look at it now. And Dan and I were both recently in this situation to an extent, we still are. So I think we'll talk a little bit about our own experience. So I'll say what I did with my four kids. So first of all, I would say that once my kids were in high school, I played it very safe with the 529s. So I put them all in cash. That's pretty conservative. Some folks are comfortable having still a little bit more stocks in the 529s once the kids are closed or in college. But I didn't. I wanted to make sure the money was there and that it was very protected. And I didn't want a bear market to cut the 529s in half while they were in college. So that's one thing. What you'll find too is in terms of the payments for the tuition and room and board and other fees paid directly to the school, you can actually have that money transferred directly to the school. So that's very handy. For other items like textbooks or maybe off campus housing, you can take the withdrawals up to the qualified amounts yourself, but then keep the receipts in case the IRS wants proof of that at some point. And I'll just highlight anecdotally, by the way, that when your kid leaves college, you might notice a slight drop in your household expenses, you know, such as food or maybe extracurriculars. Right. High school sports cost a lot of money, so some of those expenses will actually go away, which may somewhat, slightly offset the cost of going to college. Dan, do you have any tips from your own experience being a dad with a kid in college?

[B]

For sure, yeah. The one thing that I will say is make sure that the 529 expenses line up with the year that you take the money out as a withdrawal. Withdrawal. You don't have leeway. There's some other types of accounts, like flexible spending accounts for health expenses where you have a little leeway. You do not have the leeway here. Make sure you take that out in the same year. A lot of people in 529 plans there are now age based portfolios that kind of do this for you, they make your portfolio, you're investing more cautious as you get closer to the age where your child is in college to prevent the exact same scenario that BRO was talking about where you're over invested and the kids in college and suddenly you have a bear market and you're losing a whole bunch of money. So if you have one of those portfolios, that's done for you. If you don't, then it's up to you and you need to figure out what to do. Only other thing I'll say is if you have multiple kids and you anticipate having money left over from a 529 for your first child for use in the second child, sometimes that might change the way that you want to invest because it affects the time horizon. But again, that's a more individualized situation that will vary from family to family.

[A]

Yeah, and I think what Dan was kind of touching on there is, you know, you may have one 529 with one kid and you're and that kid's going to need more money, but the money in the other 529 for the other kid, maybe they don't need all of that money so that money can be transferred to the other kid. So you could almost think of these as really one big account to some degree.

[B]

Exactly.

[C]

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[A]

on to question number five from Zach. A question for you all about what to do with dividends. Do you let them get automatically reinvested? Do you prefer to have more control where they go and the timing when you purchase stocks? A discussion on dividends and all types of investment accounts would be awesome.

[B]

So Zach, I'll just say generally, it kind of depends. There are some stocks that I'm totally fine when they pay a dividend, reinvesting in more shares of that same stock. There are other stocks where I'd kind of prefer to take the cash, let it accumulate, and then potentially redeploy it somewhere else. Maybe I'll buy additional shares of that stock, but maybe I'll buy shares of a different stock. It just kind of depends on my level of conviction in that individual stock and also kind of my timeframe for that stock and my investing thesis for it. There's some stocks that you want to consistently add to. There are other stocks that I'm comfortable taking an initial position, kind of leaving it alone, adding to stocks I've had more conviction in. One thing I'll point out, when it comes to different types of accounts, I tend to avoid reinvesting dividends in taxable accounts. Here's why. It's because it makes my tax accounting harder whenever I close out that position. If you reinvest your dividends, you have all these little bitty tax lots every quarter, several times a year that you have to account for when you're calculating your capital gains. Now, admittedly, brokers are supposed to do this for you. Tax software is supposed to make this easier. But nevertheless, I like it when those purchases in taxable accounts are cleaner. In retirement accounts, not nearly as big of a deal. There's no tax impact. There are more likely to allow things to accumulate to reinvest those dividends also, in part because, like, I'm not touching that money. That money is for retirement way down

[A]

the road, I'll just point out that how you manage your dividends can be a good way to rebalance your portfolio. So if you've become overweight in a certain stock or maybe a certain group of stocks, you might want to stop reinvesting those dividends and then use that cash to buy underweighted assets. And once you're getting closer to retirement, it can be a good way to gradually de risk your portfolio. I know once I'm within five Years of retirement, I'll probably stop reinvesting all my dividends, let them accumulate as cash, maybe invest them in bonds so I can gradually get more conservative as I get closer to my retirement date. All right, it's time to move on to our sixth and final question. And it comes from Bill, who writes, I'm 44 and finally started learning about the market. I made lots of mistakes in life, but finally got to a place where I can start saving for retirement and investing. My job now doesn't offer a retirement plan. I have about $50,000 in a money market savings account and about $20,000 as my emergency fund in the same money market account. My question is, how would you guys start a retirement plan and investing in the market? I feel like I'm way behind and might need to take some risks. I believe my risk tolerance is strong. The goal is to retire with enough money to live comfortably. I only make $50,000 gross a year. I know the most important step is to try to find a higher paying job. Any help or advice would be very much appreciated. Well, Bill, so the good news is you do have an emergency fund and some savings, so that is a great start. You are likely a bit behind. Various financial services firms provide guidelines based on your age and as a multiple of your household income. I'll just take a look at T. Rowe Prices guidelines. They suggest that someone at age 45 so a year from now should have about three times their household income saved for retirement at that point. So you're not quite there, but you're also not horribly behind either. I'll point out if you're a W2 employee, you say you, you have a job. And so if you're actually being, you know, employed by that job, your only choice for retirement plan in terms of like a tax advantaged account is an IRA. So you could sock away $7,500 this year in that if you're actually not an employee of that company. If you're self employed, contractor or 1099, as they often say, you actually could open up a solo 401k and save more. Of course you do have that $50,000 in that money market account and that's, you know, pretty safe but also low returning. So if you don't need that money in the next five years, it could be invested in the stock market. And given that you likely have more than a decade until you retire, you could be very aggressive with the rest of your portfolio that you save for retirement. Assuming, of course, that you're comfortable with the ups and downs that come with the stock market.

[B]

Yeah.

[A]

I would just say that if you're relatively new to investing, I would start with a diversified collection of ETFs, maybe large caps, small caps, some international, and then you can move into individual stocks as you gain more knowledge and you get comfortable with the unique risks of owning individual stocks. I'll just close here by saying that, you know, for those who are getting a later start on saving for retirement, one of the most powerful things you could do is just work a bit longer. Right. That allows you to save more, to delay withdrawing on your savings and to delay claiming Social Security. And for every month you delay Social Security, you get a bigger benefit. So as you consider a higher paying career, which I do think is something to strongly investigate, aim to find something that you'll be happy to do well into the second half of your 60s. I know it's easier said than done, but if you find a new career, a higher paying career that you really enjoy, you may be perfectly happy working well into your 60s. You know, we had the question earlier from someone earned about $50,000 a year and is doing very well, but he retired at age 70 and that can be very, very powerful. Dan, you have any thoughts?

[B]

Only thing I'll add quickly is don't be afraid to invest for retirement in a regular taxable brokerage account. You indicate that you have a high risk tolerance investing in growth stocks that don't pay dividends for the most part. You can do even in a taxable account without paying a whole bunch of tax until you decide to sell. And if you're a long term investor like we espouse at the Motley fool, then that can be a tax efficient way to get your money working. Don't be afraid to invest for retirement in that regular taxable brokerage account. You don't have to get it all into an ira.

[A]

And that's the show. Thank you, Dan, for joining us. And thanks to Bart Shannon, the engineer for this episode. Thank you all for listening. As always, people on the program may have interest in the investments they talk about. And the Motley fool may have formal recommendations for our guests. So don't buy or sell investments based solely on what you hear. All personal finance content follows Motley fool editorial standards and is not approved by advertisers. Advertisements are sponsored content and provided for informational purposes only. To see our full advertising disclosure, please check out our show Notes. I'm Robert Brockamp. Full on, everybody.