When C-level types lay down five, six, even seven figures to scoop up shares, we listen.

After all, there is only one reason why executives buy their own stock. They believe the price is going up.

Insider buying is a great cue. But it is important for us to understand what “signal” buys look like.

Many executives have automatic buying programs, so like clockwork, we’ll see them snap up a few thousand shares at, say, the start of every quarter.

So what we really care about are sudden acquisitions across one or more insiders that fall well outside of their normal buying habits.… Read more

The market pullback we’ve seen in the last couple of weeks really hasn’t come as a surprise to me. The economy is sending what you could—at best—call mixed signals right now. And stocks, as they do in uncertain times, are reacting.

I expect more volatility ahead, so today we’re going to talk about ways to protect ourselves while maintaining the 8%+ dividend streams we’re drawing from our favorite closed-end funds (CEFs). (Read: We’re not going to cash here.)

Instead we’re going to focus on a strategy that’s been around as long as investing itself—diversification—by putting a bit more weight on assets beyond stocks.… Read more

I’d like to share my exclusive “Made for 2025” Dividend Plan with you. It’s a simple, safe strategy that identifies dividend stocks with payouts set to surge higher.

As these divvies pop, so do their associated stock prices.

The truth is, this proven system works no matter what the economy, or the Fed (or even the executive branch of the federal government!) is doing. It’s the path to peppy price gains from protected payers.

Let’s talk about a timely example—a dividend dip to enjoy! On the campaign trail, President-Elect Trump presented us with a pullback in perennial dividend grower Deere & Co (DE) thanks to these comments:

“They’ve announced a few days ago that they are going to move a lot of their manufacturing business to Mexico.

Every so often here at Contrarian Outlook, we get questions from readers about investments sporting yields that are, frankly, ridiculous. 

Case in point: The 85% forward yield (as of this writing) on a fund called the YieldMax Ultra Income Strategy ETF (ULTY): Eighty. Five. Percent.

Think about that for a second: With a 85% yield, you’re getting your entire upfront investment back in about a year. Pretty sweet deal, right?

Well, not so fast.

Before I go further, I should say that when it comes to dividends, one thing we demand at my Contrarian Income Report advisory is that a stock or fund at least “returns its yield.”… Read more

For years, it’s been a struggle to try to convince many US investors to spread some of their money abroad.

It’s only natural: We simply tend to favor the familiar—our home country—over others. Investors the world over have this natural bias.

But that’s been slowly changing in recent months. Which is great news, because diversifying internationally is a particularly smart move in times like these.

Moreover, when you diversify—especially through 8%+ yielding income investments like closed-end funds (CEFs)—you can easily rebalance your holdings in line with changes in the market, moving more into US stocks when they’re low, say, and international assets are high.… Read more

The stock market is currently caught up in its deepest slide since July. We contrarians are prepared to move quickly for deep-dip-buying opportunities.

Right now, I’m paying close attention to already-high-paying corners of the market, where we can get 9.4% to 13.1% yields right this very minute. I’m talking about from the business development company (BDC) industry, where those sky-high yields aren’t rare—they’re the norm. In fact, right now, if we threw darts at a board of BDCs, we’d be likelier to hit a double-digit payout than one in the single digits.

But it’s not just the yields I love—it’s the access.… Read more

There are two things I need to bring to your attention right now, especially if you’re an income investor. One is my outlook for the market, as volatility really hits home.

The other is a 15.6%-yielding(!) fund that just changed its name and ticker—and really grabbed contrarians’ attention in the process.

Let’s start with what’s really going on with this wild market.

The NASDAQ is now down more than 10% from its peak price, and stocks on the whole are down for the year. I don’t expect this to last very long. My take: 2025 is likely to be a year of volatility rather than a year of decline.… Read more

“I don’t have to make and update my goofy spreadsheets anymore!” my man Peter B. from New Hampshire writes.

Tell ‘em, Peter!

We are devoted to retiring on dividends here at Contrarian Outlook. But a little bit of work in retirement is OK. As income investors, we should be able to forecast our income.

Note that I said a little bit of work. Not a lot! I am not interested in fiddling with spreadsheets until the end of time, and neither is my man Peter.

If you’re with us, why not hop aboard the Income Calendar train with Peter and me?… Read more

At this point, I don’t think I really need to say that Trump 2.0 is a lot different than Trump 1.0. And one of those differences—which very few people are talking about—is a huge tailwind for the two big dividends we’re going to dive into today.

Think back to our first go-’round with Trump. Remember his relationship with Jay Powell? Terrible, right?

Back in 2018, he tweeted that Powell and the Fed had “no sense, no guts, no vision” when they failed to cut rates as much as the president wanted. A year later, he called Powell an “enemy.”

And that’s just a small sample of the torment unleashed upon poor Jay!… Read more

I recently got some reader feedback that made me realize something: When it comes to our favorite income investments—8%+ yielding closed-end funds (CEFs)—there are still a lot of misconceptions out there.

It’s key that we put those right, because they’re causing some investors to miss out on CEFs, and the big (and often monthly) dividends they provide. And I know I don’t have to tell you that in turbulent times like these, high payouts like those are a lifesaver.

This reader wrote in response to a recent piece I wrote about how CEFs can be better than ETFs, pointing out two things:

1. The three CEFs I mentioned in the piece have higher expense ratios than passive funds.