5 Steps to Turn $500K Into $41,869.76 Per Year

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$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 $41,869.76 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

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If you’re reading this, I probably don’t have to tell you that the stock market beats most (all?) other ways of building wealth.

It’s not even close!

Over time, the S&P 500 has generated around a 10% annualized return. But of course, that line does not go straight up and to the right. There have been long periods when stocks have moved sideways, and occasional years (I’m looking at you, 2022), when they’ve taken a header.

At those times, in particular, we’re all keenly aware of the S&P 500’s lame dividend yield (around 1% as I write this). It means that those who hold, say, an index fund and need cash face the soul-crushing prospect of selling at a low (or maybe even a loss).… Read more

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Washington has a debt problem going into 2026. To put it mildly.

Policymakers are desperate to boost demand for US Treasuries. Higher Treasury prices mean lower Treasury yields. Lower yields translate to reduced interest payments for Uncle Sam on his huge federal debt pile.

The interest payments are what policymakers care about. The total debt is mind-blowing and will never be paid down. The interest, on the other hand, is an annual budget item.

How to reduce the interest via lower bond yields? Leave it to the Washington suits, who “did their thing” with the bills coming increasingly due. They engineered new demand for their government IOUs.… Read more

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There’s one 68% (!) paying fund out there that will give us a lump of coal this Christmas, if we’re not careful enough to avoid it.

I’m talking about the YieldMax Ultra Income Strategy ETF (ULTY), which we last discussed in September. Its 68% payout is so ridiculous that you could be forgiven for wondering if I missed a period between the 6 and the 8.

It’s easy to see how one could fall for a payout like that. As 2025 wraps up, we’re looking at a third straight year of double-digit gains for the S&P 500. Nothing breeds complacency like a levitating stock market!… Read more

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Stocks are about to do something almost totally unheard of: chalk up three winning years in a row.

And no one is celebrating.

Instead, worry is everywhere: about an AI bubble. Sticky inflation. Or the Fed—everything from the bank’s next chair to its independence and the direction of rates.

This combo—a strong market tempered with a big dose of anxiety—has set up a rare setup in our favorite high-income plays: 8%+ yielding closed-end funds (CEFs). It comes in the form of a pattern I don’t see often, but when I do, it’s almost always a buying opportunity.

That pattern is the following: A drop in a CEF’s market price (driven by investor sentiment), while its underlying portfolio (driven by management’s talents) keeps on growing.… Read more

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The manic market has been dumping business development companies (BDCs) left and right. Let’s talk about a seven-stock BDC portfolio (yielding 13.5%!) that is poised to bounce back when sanity returns.

BDCs, which lend money to small businesses, are on the “outs” with the Wall Street suits after countless soft jobs reports. The spreadsheet jockeys fret about an unemployment-induced economic slowdown and miss the real story: small businesses are making more money than ever thanks to AI.

Here is what’s actually happening in the Main Street economy:

  • Employers—especially nimble small business owners—are implementing AI to streamline and even run their operations.

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Every year, the stock market has a theme. And I’ve got a pretty good idea of what 2026’s will be.

Simply this: If you buy stocks in the new year, your return will be zilch—at best—for a decade. Maybe more.

Why do I say that? Because the market’s price-to-earnings (P/E) ratio is high by historical standards.

Trouble is, most people are reading this popular indicator all wrong. That disconnect (and the fear it’s starting to cause, which could get worse in 2026) is setting up a nice short-term buying opportunity for us.

Valuation worries are being amplified by this chart from Apollo Global Management, which could easily become the poster child for fearful investors next year:

It comes from Apollo’s chief economist, Torsten Sløk, who notes that the estimated returns we should expect from the S&P 500 over the next decade are zero.Read more

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2026 is shaping up to be the best year for bond investors in many years. Washington wants rates down, housing up and borrowing cheap again.

This wish list is wildly bullish for bonds.

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.

President Trump has confirmed his shortlist for the next Fed Chair is down to “The Two Kevins”: Kevin Hassett and Kevin Warsh.… Read more

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Today I have a sweet dividend “double shot” for you: The first? A 2.8% payout set to grow thanks to AI—and take the stock price up with it.

The second gives you high payouts now, in the form of a monthly-paid 7.8% divvie that also looks set to head higher.

Both of these tickers are cheap. In fact, they (and the sector they’re in) could very well be the last bargains on the board as the bull runs into its fourth (!) year.

Pharma Goes From “Dead Money” to the Next AI Winner 

These two dividend plays are on sale because they’re often lumped in with drug stocks—a sector that’s lagged for years.… Read more

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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

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