Dan Caplinger

speaker

1,715 appearances 16 recordings 4 series first heard Oct 2023 last heard 6d ago

Dan Caplinger’s voice in public audio — every appearance, attributed to the second.

Trend

recordings per month · last 12 months

Recordings per month over the last 12 months — 15 in all, peaking in Nov 2025 with 3.

Appearances

newest first · ▶ plays the moment

Motley Fool Hidden Gems Investing · Mailbag! Maximizing Dividends, Spending in Retirement, Managing a 529 · 20 Jun 2026 podcast

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.

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 are 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 or 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.

Showing 361–380 of 1,715 · page 19 of 86