ChatGPT? Nah. This Is Your Best “Assistant” for Dividend Investing

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Look, I know what a pain it can be to track your dividends.

ChatGPT? It’s no help. When I asked if it could give me a hand, its top suggestion was that I use a spreadsheet!

I mean, I guess the offer to help set up formulas is appreciated. But this is still a pain to set up—with AI assistance or not.

Sure, your brokerage account might have a built-in dividend tracker, but it’s almost certainly only useful for any investments you hold with that particular broker.

But what if you hold investments in more than one account, or with more than one brokerage (as many of us do)?… Read more

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Rate cuts are finally here. So will we actually hit that vaunted “soft landing” everyone’s been talking about?

Well, I’ve got a (contrarian, naturally!) take that I know most people haven’t thought about—especially since last week’s jumbo 50-point rate cut dropped:

What if we hit a “no landing” scenario, where the economy ticks along and inflation comes back?

I’m bringing up that unpleasant idea because, usually in a rate-hiking cycle like the one that just ended, the central bank pushes the Fed funds rate higher until it breaks something. 

But this time, it’s not clear it has.

In fact, when it looked like it finally had—when Silicon Valley Bank and friends crumbled to dust in March 2023—Jay blinked, and pumped liquidity into the market through the back door, a move we’ve referred to as “Quiet QE” here many times before:

The Fed Didn’t Break Anything This Time—That May Be a Problem

With that in mind, last week’s oversized cut was understandable: The Fed has been keen to take its foot off the brake for a while now.… Read more

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Believe it or not, your favorite income strategist once had a multi-year stint as the head of human resources for a US-based software company.

It was, coincidentally, my last regular “day job” before I drifted into the world of stocks and startups.

When my old boss, our managing director, handed me the task of hiring our new employees, he gave me this piece of wisdom.

“I trust you to make the call. Just one thing…” he winked at me.

“The kids must be graduates from Berkeley, Cornell, MIT or Stanford.”

Gee, thanks boss. Like it was an easy task to convince a new graduate from an elite engineering school to skip the offer from Google to work with us.… Read more

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“Hey Brett, how’s business?”

“Awful,” I admitted. “But we’re a startup. If we can improve from awful to simply bad, it will be a big milestone for us.”

That was one economic meltdown ago, back in 2008. I had just left my “day job” to start my first company. On cue, the Great Recession descended upon us.

But the gloomy economic backdrop didn’t matter. Actually, it was a blessing. A recession is actually the best time to start companies and grow them.

As a startup with no money, we were able to cobble our limited resources together to get the company off the ground.… Read more

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There’s an obvious reason why we love closed-end funds (CEFs): the dividends!

CEFs’ payouts average around 7% as I write this, and there are plenty paying well into the double digits. One fund we’ll touch on below, for example, yields more than 16%. A payout like that gets you $2,000 a month in dividends on just $150,000 invested.

But, as we often discuss in my CEF Insider service, when picking CEFs, we always need to look past those big yields.

We also need to examine the discount to net asset value (NAV, or the value of the fund’s portfolio) because buying a CEF at an unusually wide discount can net us strong price upside as that discount bounces back to normal, pulling the price up with it.… Read more

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Anyone up for a 10.2% payout? One that is powered by profits that should actually rise alongside interest rates?

If so, I’ve got a three-letter acronym for us:

B-D-C.

Business development companies provide debt, equity and other financing to small and midsized companies, effectively acting as banks because banks often don’t want to take on that level of risk. And because they’re primarily investing in companies that aren’t on public markets, BDCs serve as de facto private equity investments—but ones that retail investors like us can get in on!

BDC structures are similar to real estate investment trusts (REITs). Both were created by Congress—REITs in 1960, BDCs in 1980.… Read more

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If you’re like most people these days, you’re desperately searching for any kind of meaningful dividend stream.

Finding one is no easy task. The S&P 500, after all, yields 1.5%, on average. Treasuries? With their 0.9% yields, they’re not even worth talking about.

With the old income go-tos off the table, plenty of folks are looking further afield. Some are boosting their holdings of high-yield bonds through exchange-traded funds like the SPDR Bloomberg Barclays High Yield Bond ETF (JNK). Others are going with more esoteric investments, like high-yielding business development companies (BDCs), which you can tap through the UBS Etracs Business Development Company ETN (BDCS).Read more

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Today I want to show you how you can retire on $405,000—and with just five buys, too! Put together, these five stocks and funds hand you a 7.4%-yielding portfolio that will pay you reliably for decades.

First, though, let’s quickly run through how our “5-buy” portfolio will work—and how it proves the so-called “experts,” who say you need a million dollars or more to clock out—are dead wrong.

A Million-Dollar Retirement … for $405K!?

To be smack in the middle of income in America, you need to bring in about $30,000 per year. So, at a 7.4% yield, you’d need to invest $405,000.… Read more

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Not yet as rich as you always wanted to be? Don’t worry, because today we’re going to dial you in for some “rich guy” dividend favorites that’ll pay you up to 9.9% every year.

Private equity is a lucrative and secretive world. It’s often limited to accredited investors, which means these funds require you to have $200,000 or more in annual income to qualify.

If you’re living on dividends alone, this might be challenging. Fortunately, there are some private equity plays that you can buy just like individual stocks. They trade for as cheap as $12 per share and they’ll pay you dividends from 8.8% to 9.9% along the way:

Private equity (PE)—funds that can invest in the equity and debt of privately held companies, which we typically can’t get our hands on—is generally touted as outperforming the stock market.… Read more

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Most income investors find their way to business development companies (BDCs) by screening or searching for big yields. And there’s no doubt these listed payouts do appear impressive! Here are the five largest BDCs (ranked by assets under management):

A first-level look at this table may have you wondering why anyone would buy MAIN when they could nearly double their dividend by choosing another ticker. Well, there’s a good reason that we’ll get to in a minute. First, let’s talk about what BDCs actually do so that we can understand what is driving these big dividends.

It all started in 1940, when Congress passed the Investment Company Act.… Read more

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