The recent blowup at Situational Awareness, a hedge fund run by a so-called AI “whiz kid,” tells us a lot about the mindset of the mainstream crowd these days—and what we need to do to avoid falling victim to it.

In fact, the same selloff that broke Situational Awareness put one of our favorite tech CEFs on sale. More than that: This steady payer is trading near discount levels not seen in more than a decade.

An AI Fund Built on Hype and Debt

After working at OpenAI (and being fired in April 2024), Leopold Aschenbrenner wrote an essay called “Situational Awareness” that got a lot of attention and later became the name of his hedge fund.… Read more

You ever buy a stock, watch it go up quickly, feel like a genius…only to watch it top out and take back some of your gains…and then all of them? It’s a—let’s admit it—stupid feeling.

The winner, now a big fat loser. Why didn’t I take the money and run!

“Be patient,” they say. “You’re here for the dividend. The stock will come back.” Well, first, who the heck are they? And second, why should patience be required? It was a fast winner. Now it’s a big fat loser!

Well, my careful contrarian, I ran the numbers earlier this year.… Read more

Kevin Warsh is talking tough on inflation. The bond market is calling BS.

Whenever the Fed and the bond market face off, it pays to remember the words of “Ragin’ Cajun” James Carville:

“I used to think that if there was reincarnation, I wanted to come back as the President or the Pope or a .400 baseball hitter. But now I would want to come back as the bond market. You can intimidate everybody.”

Until this fight gets straightened out, we’re in for some turbulence.

We contrarians are here for it. When markets roil, the crowd tosses perfectly good payers over the side.… Read more

A Chinese startup is disrupting the AI world. Middle East worries are spiking oil.

These are the two biggest worries rocking markets now. And if you’re like me, you’re feeling a sense of déjà vu.

Let me take you back to February, when talk of a fight between Iran on one side and America and Israel on the other caused oil to soar and markets to sell off. Right now, that story is repeating (as it has many times as the conflict has ebbed and flowed).

On the AI side, variations of this story have been coming and going since early 2025, when a Chinese company created DeepSeek, a powerful, energy-efficient AI model.… Read more

Hey, remember tariffs? Well, they’re baaaaaaaack!

As of last week, new import taxes of 10% to 12.5% were slapped on 60 trading partners. This covers a cool 99.4% of everything that America buys abroad. Let’s pile the tariff return on top of the recent Fed news and tensions that keep rolling in the Middle East. There’s obviously plenty of bricks in the current Wall Street wall of worry for this stock market to climb.

This climb, however, is no problem for “low drama” dividends like these. I’m talking about five companies yielding between 4.9% and, get this, 11.5%! No matter the headlines these payouts keep flowing.… Read more

Most investors love to talk about their winners. That’s understandable, but it’s still a shame, because losing investments can often teach us a lot more.

That’s true no matter what you invest in: stocks, real estate—and, yes, 8%+ paying closed-end funds (CEFs), our favorite income plays.

With that in mind, let’s look at three of the worst-performing CEFs of 2026 to see what they got wrong and how we can avoid holding such funds in the future.

I haven’t chosen this trio at random; these three CEFs are the worst performers on the market so far and have market caps above $250 million.… Read more

$500K can be enough money to retire on. Even as early as age 50!

The trick is to convert the pile of cash into cash flow that can pay the bills. I’m talking about $42,839.91 per year in dividend income on that nest egg, thanks to 8%+ average yields.

These are passive payouts that show up every quarter or, in many cases, every month.

Meanwhile, we keep that $500K nest egg intact. Or, better yet, grind that principal higher steadily and safely.

Got more in your retirement account? Cool—more monthly dividend income for you!

We’ll talk specific stocks, funds and yields in a moment.… Read more

When the world is burning—as it feels like it is now—it pays to remember the words of Howard Marks, the smartest money manager most people have never heard of.

The essence of Marks’s approach is contrarian thinking. In Chapter 11 of his excellent book, The Most Important Thing: Uncommon Sense for the Thoughtful Investor, he writes:

The ultimately most profitable investment actions are by definition contrarian: You’re buying when everyone else is selling (and the price is thus low), or you’re selling when everyone else is buying (and the price is high).

But he admits this isn’t easy: “These actions are lonely and uncomfortable.”… Read more

Imagine a credit fund that yields 15.3% and is built to deliver strong returns in all rate environments. That’s the promise of a closed-end fund (CEF) called the XAI Floating Rate & Alternative Income Trust (XFLT).

But the fund has, unfortunately, not backed that up with strong performance. As we can see in orange below, XFLT has badly lagged the popular S&P 500 index fund (in purple) since its launch in 2017.

A Laggard, Even With a 15.3% Yield

That performance amounts to just a 0.57% annualized total return! That’s less than many of the high-yield savings accounts offered by regional and national banks.… Read more

Why sit around and wait all quarter long for a dividend payment?

Monthly divvies are where the retirement party is at! These income “cheat codes” arrive alongside our bills and recurring expenses. What a concept!

But be careful because some monthly payers don’t pay enough to matter. Take Permian Basin Royalty Trust (PBT), which pays monthly but these divvies add up to just 1.2% annually. Gee, thanks.

$1M Invested in Either Would Pay Under the US Poverty Line

We need monthly payers that are committed to maximizing not just the frequency of shareholder rewards, but the size of the payout.… Read more