Articles

One thing I’ve always been astonished by is how fast a winning strategy (in investing and in life!) can suddenly slam into a wall—and start causing a lot of pain.

Consider, for example, the life of a mortgage banker in the 2000s: They made easy money for years, then the subprime-mortgage crisis threw them out of work overnight.

This happens in investing, too, which is why it’s always good to stay humble and well-diversified. Some high-yielding closed-end funds (CEFs), for example, look like big winners at any given moment. But if you buy without looking under the hood, you’re risking sharp losses.… Read more

Covered-call strategies can be an income investors’ best friend. Whether the broader stock market goes up, down or merely grinds sideways, selling covered calls pays.

Fortunately, we can buy covered-call funds that do the heavy lifting (“call writing”) for us. These funds yield 7%, 12% and yes even 89%. We simply buy them and collect the dividends.

But are all covered-call funds good buys? Of course not. We’ll sort through a popular four-pack in a moment. First, let’s discuss what covered calls are and how they generate income.

Degenerate traders love buying call options to make big bets on stocks.… Read more

Today we’re going to talk about a subject that might seem a little outside the dividend plays we normally discuss.

But as you’ll see, this topic—a big shift in how Americans feel—is the main reason why some of our favorite high-yielding closed-end funds (CEFs) are woefully underpriced, like one equity-focused 9%-yielder with an incredible track record.

Let’s start with that unlikely topic: Happiness. It matters because, as we’ll see, how happy Americans are ties directly into investing behavior in very predictable ways.

Source: CEF Insider

This chart shows the results of the General Social Survey, from the University of Chicago’s National Opinion Research Center.… Read more

Is your portfolio on track to yield 26% in 2026?

If not, why not?

Of course, most stocks and funds don’t pay 26% on their own. But it’s a quick fix to get many of them to.

This makes a big difference to our retirement goals: a 26% return on a million-dollar portfolio is $260,000 in cash flow per year! Without tapping the principal.

Or $130,000 in cash flow on $500K. You get the idea. With 26% coming in, it’s a lot easier to retire.

How can we boost our investment income like this? Let’s take boring ol’ SPY—SPDR S&P 500 ETF Trust (SPY)—as our first example.… Read more

Investors are scared—and that’s setting up a terrific opportunity for us in 8%+ yielding covered-call CEFs.

That’s because volatility fuels the income these stout funds get from their option strategies. And that income flows right into our dividend checks.

I’ve got two 8%+ payers delivering growing “option-boosted” dividends for you below.

And thanks to the market’s relative calm these last few months, these funds are bargains. But the last four years of history say we’re likely headed into a storm. That’s because three of those years started with stocks tripping over their shoelaces.

I think 2026 will make it four out of five.… Read more

The bankruptcy of auto-parts supplier First Brands has hit a corner of the market known for high dividends. Does that make these assets bargains?

Maybe. But we need to be careful here, and avoid making the mistake of “reaching for yield”: that is, buying yields that are high for a reason: the stock price has plunged.

But I’m getting ahead of myself. The corner of the market I’m talking about is business development companies (BDCs), which loan money to small- and mid-sized firms.

Investors first got worried about BDCs a couple months ago, when the First Brands story broke. The news raised alarm about the private-credit market (where BDCs operate).… Read more

Small-cap stocks have finally started to wake up lately, which could be a bullish sign as we head into 2026. Let’s remember that a smaller market capitalization does not necessarily mean a diminutive dividend—today we’ll discuss four small caps that yield between 7.1% and 13.3%.

It’s been a “lost decade” for small caps, which have lagged their larger brethren. 2020’s COVID reopening rally in small caps was intense but short-lived—rising interest rates, renewed interest in safer mega-cap stocks after two bear markets in three years, and a rush into predominantly large-cap AI stocks have left small caps on the outs going into this year.… Read more

When most people think about the soaring stock market, they’re really only thinking back to the end of 2022, when it feels like it all started.

I know. 2022. A year we’d all like to forget.

But looking back only that far ignores the fact that the S&P 500 is a long-term wealth generator—a really long-term wealth generator, in fact. Over the last century, it’s posted a 10.6% annualized return.

Over the last 10 years, it’s done even better, returning a robust 14.6%.

I bring this up because it’s easy to lose sight of that these days, with the news cycle constantly amping up the fear, most recently on worries about an AI bubble.… Read more

Let’s get our 2026 dividend shopping finished ahead of time, shall we?

Come January, we’ll have plenty of company from vanilla investors, rushing to “figure out the new year.” Trends. Predictions. Buy this!

But there’s no reason to wait. We already know some of the key dimensions of 2026. Interest rates, for one, are on their way down. Fed Chair Jay Powell has delivered two rate cuts to end the year, with more to follow.

Whether or not Powell personally delivers them doesn’t matter to us. Powell is on his way out. But the Fed show will go on, with a ringmaster ready to roll.… Read more

The spreadsheet jockeys on Wall Street have it all wrong—and their blunder is dragging down the average investor’s returns (and income!).

Their mistake? Looking at “old school” measures, like the recent spate of soft jobs reports, and jumping to the conclusion that the economy is hitting the skids.

Trouble is, this take is totally disconnected from reality, especially when it comes to the nation’s small businesses. Because these mom-and-pop shops are still upbeat—and many of them are looking to grow.

The proof is in the numbers. First up, even though small biz optimism did tail off a bit in October, according to the NFIB Small Business Survey, it’s still above its historical average, where it’s been for the past six months.… Read more