Last month, we hit the contrarian karaoke bar together. No judgment. It was a good time!

If you’ve got a (ahem, no judgment) fuzzy memory, well, here’s how it went down. We sang some Billy Joel—good start, I know.

A little We Didn’t Start the Fire. We honored his point that the chaos never stops. That was the case in 1989 when the banger topped the Billboard charts. It remains true today.

Ha, we even belted a 2026 verse over our (virtual) beers!

Venezuela, Davos snow, Iran missiles here we go

Greenland borders, tariff fights, Powell keeping money tight

Wow.… Read more

Wall Street is mired in another panic over AI. And we contrarians are here for it.

Our play? As always, we’re going where first-level investors aren’t, quietly snapping up dividends AI is set to supercharge.

I’m talking specifically about an overlooked opportunity in drug stocks, which are about to see the value of their R&D dollars get a big boost from AI. We’re going to tap in with an 8.8%-yielding closed-end fund (CEF) that’s trading for 11.4% below its “true” value.

That discount exists in part because investors—worried about how AI may disrupt sectors like software—are ignoring pharma, and the accelerated product cycles (and cash flows!)… Read more

Today I want to get into a question that comes up on the regular in 8%+ yielding CEFs:

What if you run across two of these income generators that seem to be equal in pretty well every way. Can you just buy one or the other?

Truth is, sometimes you can and sometimes you can’t, but it’s not always clear when simply closing your eyes and picking one fund is the right move. That’s because with CEFs, there are a lot of moving parts one needs to pick apart and look at carefully.

Let me show you what I mean with two CEFs holding real estate investment trusts (REITs)—publicly traded “landlords” holding properties ranging from senior-care facilities to malls and warehouses.… Read more

“Time out.” I yelled it with a hint of disgust. I didn’t even have to make eye contact with my assistant coach—we were on the same page.

We’d just watched the second air-ball three-pointer of the second half.

“Get in there for Reese.”

Reese shrugged and jogged off the court. I grabbed him lovingly by the shoulders. “Hey buddy — do you know why you’re out?”

He nodded slowly. “Because…I…shot… a…three…pointer.”

“And what did I just say in the huddle?”

“…To…not…shoot…three…pointers.”

I patted him on the shoulder. Reese was back in the game in two minutes. But I had to make the point.… Read more

There’s one critical takeaway for us as AI flits through the market, whacking sector after sector as it does:

Actively managed funds—closed-end funds (CEFs), in particular—are the best way to play it. 

Funds with human managers are often viewed as dinosaurs by the AI crowd and those obsessed with low-fee ETFs, but they shouldn’t be. Because when it comes to investing in a sector as complex, and fast-changing, as tech, we need an insider in our corner, spotting, and moving ahead of, the next shift before it hits.

I’m talking about a real person who talks to other pros in the business and uses their own personal tech background to get at the insights others miss.… Read more

Oh, the joys of home ownership. We found a moldy corner last week. And not a little spot, either.

A full farm thriving behind a brigade of stuffed animals wedged against the wall. (The stuffies block the airflow, providing cover for this ecosystem.)  

Now Waiting Their Turn in the Laundry Line

“I see this every day in the homes down here,” the abatement guy explained his frequent trip to my old-home neighborhood. “Usually behind furniture jammed against the wall.”

Well, it’s the cost of doing business. The home has character. We like living downtown—makes us still feel kinda cool, sharing sidewalks with the neighborhood “kids” (anyone under 35) who live without stuffed animals upstairs.… Read more

There’s a group of stocks out there that most people think yield just 2%—or less.

But they’re way off. In reality, these “elite” payers yield 2X, 3X—and in the case of a stock we’ll talk about below, even nearly 4X that. I’m talking about a tidy 8.3% shareholder yield (remember that phrase) here.

This one has another advantage we love in a market like today’s, too: Its management team “buys the dips” in the share price for us. We don’t have to do anything at all!

Stocks like this are perfect for times like these, with the economy still ticking along nicely.… Read more

One of the most expensive mistakes CEF investors make? Chasing a fund’s discount.

That would be the discount to net asset value (NAV).

A big discount has a lot of appeal because it essentially means we can buy a CEF’s assets—stocks, bonds, REITs, utility stocks, you name it—for less than we could if we bought them ourselves on the open market.

So it makes sense that we should always go for the CEF with the biggest discount, right? After all, CEFs pay dividends north of 8%, on average—with the portfolio of my CEF Insider service paying even more: 9.3% as I write this.… Read more

I hadn’t seen my boy in years. He wasted no time laying into my career decisions.

“Why are you messing around with the finance stuff? The blogging? No future in it.”

Well, good to see you too, buddy.

“You have real value in the software thing you’re doing. Stick with that.”

His advice was to leave Wall Street to him. He worked for a big-name firm. At the time of our run in, we were five or so years out of undergrad.

In true contrarian form, I ignored him. And it’s a good thing! Here we are talking stocks together and the software startup he wanted me to focus 100% on?… Read more

Suddenly, investors think AI is bad for software companies.

The truth? This whole story is a red herring. The real tale here is one of gains—and dividends—not losses. And we can nicely tap in with a fund sporting unique “downside insulation” and an 8% dividend, too.

Why the Software Selloff Is Overdone

Truth is, the premise of this whole argument is wrong, especially from an investment standpoint, and the reason why has a lot to do with timing: This bear market in software that’s shown up in less than a month and on news that’s, frankly, flimsy.

To wit, the selloff began because of a new product by Anthropic.… Read more