Three High-Yielders Up to 10.8%, 36 Dividend Checks a Year
Brett Owens, Chief Investment Strategist
Updated: October 14, 2025
Own a portfolio stocked with S&P 500 stocks? Or maybe an S&P 500 index fund?
It’s okay if you do. We won’t judge (well, maybe a little bit!). But answer me one question (without checking your brokerage account).
How much in dividends will you collect in November?
If you’re like most people, you don’t know. And if you do, you have a much better handle on your quarterly paying holdings than most (or maybe you’re using our AI-powered dividend tracker, Income Calendar!).
It’s understandable if you can’t come up with this number off the top of your head. Let’s drop a fictional $100K into five major Dow Jones Industrial Average stocks—Coca-Cola (KO), Procter & Gamble (PG), UnitedHealth (UNH), International Business Machines (IBM) and Boeing (BA)—and see what Income Calendar comes back with.
Popular Stocks Generate “Cash-Flow Chaos”
Source: Income Calendar
Lumpy and, well, pretty lame—just a 2.1% average dividend! But I’ll tell you who likely can tell you exactly how much dividend cash they’ll bank next month: investors who hold monthly dividend payers in their portfolios.
These stocks and funds nicely balance out any quarterly payers we may own by providing a predictable monthly payout we can think of as a baseline, rolling in just as our bills do.
We’ll dive into three strong monthly payers that are precisely the right tools for this job below. First, let’s split our $500K among them and flip them into Income Calendar so we can see what kind of monthly dividend we can expect:
Big, Steady Payouts Dividends From These 3 Monthly Payers
Source: Income Calendar
That’s better! Plus, we get TRIPLE the yield here—6.7% on average! (And as we’ll see below, thanks to the special dividends offered by one of our picks, we could end up with more than that.)
I chose to focus on three tickers because they come from the top-three places to find monthly payouts: closed-end funds (CEFs), business development companies (BDCs) and real estate investment trusts (REITs).
Let’s start with the CEF, since it sports the biggest yield of our trio—an outsized 10.8%. And it’s thrown off the odd special dividend, too.
DoubleLine Income Solutions Fund (DSL)
Dividend Yield: 10.8%
Few people realize it, but yields on long-term bonds—10-year Treasuries, specifically, are capped. Think they’ll break 5%? Think again! These days, Treasury Secretary Scott Bessent is running some “yield-curve control” that, I’ll be honest, makes the capitalist in me cringe.
These moves are likely to mean lower interest rates for borrowers, with the 10-year yield setting the pace for consumer and business loans of all types—including mortgages.
The DoubleLine Income Solutions Fund (DSL) is our play here.
Bessent is leaning on short-term issues to fund Uncle Sam’s massive debt. It’s a practice Janet Yellen started, and Bessent once criticized—but then not only continued but amped up when he took over. Nowadays, he’s funding 83% of debt issuance short term.
The takeaway is that these moves lower supply of long-term Treasuries, boosting their prices and cutting their yields—pushing down long-term rates in the process.
Bond funds trade opposite interest rates, so that’s thrown a floor beneath corporate-bond funds like DSL.
That’s the macro side of our case. The micro side is this one is run by the “Bond God,” Jeffrey Gundlach, who has a long record of being right—and whose recent call for gold to hit $4,000 just came true.
He’s built a portfolio of mainly below-investment-grade corporates with relatively long durations (around 5.4 years on average). This is where the best bargains lie.
Moreover, longer-duration bonds will likely rise in value as rates fall. That’ll juice DSL’s portfolio and its divvie, which has rolled in steadily since inception, only pulling back a bit in the COVID chaos. And as you can see, big special dividends abound:
Source: Income Calendar
And we’ve got another sweet setup, too, courtesy of DSL’s discount to net asset value (NAV, or the value of its underlying portfolio).
Everything Is Going DSL’s Way—and Mainstream Investors Still Missed It
As you can see, this one has traded at a premium for most of the last year but has suddenly dropped to a discount. With the tailwinds behind DSL, there’s no reason for this deal. Let’s buy in before it’s gone.
Main Street Capital (MAIN)
Dividend Yield: 7.4%
BDCs also gain from this rate setup. That’s because these companies, which lend to small and mid-sized businesses, have a large slice of their loans tied to the Fed funds rate (which, as we’ve been discussing, is likely to keep falling).
That would hurt BDCs’ loan rates, but we’re talking about a slow move. The economy is still strong, with the Atlanta Fed’s GDPNow indicator—the most up-to-the-minute gauge we have—estimating healthy 3.8% growth for the just-finished third quarter.
That means more chances for BDCs to spur new loans—with MAIN, one of the biggest BDC players, likely to grab a healthy share. Moreover, while MAIN doesn’t get specific, it did note in a recent investor presentation that its floating-rate loans “generally” include minimum “floor” rates.
The firm also says that 79% of its outstanding debt obligations are fixed rate, while on the lending side, 66% of its debt investments (i.e., loans outstanding) are floating-rate. That gives MAIN some built-in insulation on both sides of the balance sheet.
Then there’s the 7.4% yield, including MAIN’s regular special dividends. Moreover, over its 18-year history, this ironclad lender has never cut or suspended its regular payout, even during the pandemic or financial crisis. Check out this lovely payout picture:
Source: Income Calendar
(And to be clear, those dips in the chart above aren’t reductions—they’re those “supplemental” payouts I just mentioned, as are the spikes.)
No wonder MAIN has trounced the BDC index fund since that fund’s launch in 2013:
MAIN Gives Us ETF-Style Diversification—While Crushing ETFs
I expect more from this generous payer as rates quietly shift in its favor—and mainstream investors, fixed as they are on what the Fed is doing, slowly start to notice.
STAG Industrial (STAG)
Dividend Yield: 4.1%
STAG Industrial (STAG) is profiting as more US companies come home—a trend we’ve been talking about for years—driving up demand for warehouse and factory space.
The thing I like most about STAG (beyond the payout!) is that management has put on a masterclass in risk management, making sure no tenant accounts for more than 3% of annualized base rent. STAG is also picky about who it chooses to rent to: 84% of tenants have revenue above $100 million.
Then there’s the dividend, which yields 4.1% and is paid monthly. That is a smaller yield than MAIN and DSL, but that makes it very reliable: As I write this, the dividend occupies 68% of the midpoint of STAG’s 2025 FFO forecast—very safe for a REIT.
The firm has more than made up for that in price gains: in the last decade, STAG has tripled investors’ money, compared to a “meh” total return for the go-to REIT ETF.
STAG Leaps Past Other REITs
With 97% of its operating properties occupied and rental revenue rising sharply—up a fit 9% from a year earlier in the latest quarter—the company’s outlook is solid. That makes this 4.1% monthly dividend a nice pickup to bring some monthly predictability to the quarterly payers you’re now holding.
Turn Your Portfolio Into a 10.2% Monthly Income Machine
As I just showed you, there are plenty of monthly dividend stocks out there—you just need to go a little beyond the S&P 500 names most people stick with.
REITs, BDCs, CEFs and, yes, some regular stocks offer monthly payouts. But you still need to separate the winners from the pretenders.
