The Dividend Mailbox®

The Dividend Mailbox®

We want to stuff your mailbox with dividends! Our goal is to show you the power of dividend growth investing, and for each year's check to be larger than the last. We analyze specific companies and look at the mindset this strategy requires to be successful long-term. Come explore this not-so-boring world and watch your portfolio's value compound.

Episodes

June 24, 2026 35 mins

The news says the market is down, up, sideways... but which market? The Dow, the S&P 500, SCHD, gold, real estate—on any given day, they're all doing something different. If you don't know which market is actually yours, sooner or later, one of the others will seduce you into a move you'll regret.

In Episode 60, Greg takes on a question that sounds almost too simple: What is the market? Using six real-world examples—...

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Everyone's talking about what AI is going to disrupt. The question most investors aren't asking: What happens after that disruption, and who actually wins? The obvious answer and the right answer are rarely the same thing. 

In this episode, Greg introduces a framework he first encountered through Howard Marks: first-level vs. second-level thinking. First-level thinking reacts to what's in front of you. Second-level thinking fol...

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Real estate investors don't think of themselves as dividend investors. Neither do venture capitalists or business owners collecting profit distributions. But strip away the labels, and every one of them is doing the same thing: buying a stream of income and betting it grows. The wrapper is different. The logic is identical.

To prove it, Greg walks through three real investments, all made in 2013, with the same $535 million starting ...

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Sysco ($SYY) just announced the acquisition of Restaurant Depot in a $29 billion deal — and the market didn't like it. The stock fell more than $10 in a single day, briefly dipping below $70. 

Did this deal break the dividend growth story… or create a rare opportunity for long-term investors? 

Most acquisitions destroy shareholder value, but this one is more complicated. The deal expands Sysco's revenue base by...

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Markets feel uncertain. Headlines are driving sentiment. Oil prices are volatile, and cracks are forming in private credit, making high yield look more attractive than ever. But is that yield actually protecting you, or pulling you into risk?

In this episode, Greg looks at three real-world examples to examine how income behaves under pressure and what that reveals about portfolio stability. 

We break down private credit and the ...

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Dividend Growth: The Quiet Engine of Wealth 

Dividend growth investing sounds simple, but doing it well for decades is not. That’s why we wrote Dividend Growth: The Quiet Engine of Wealth—a practical guide to building a framework you can stick with when things get uncomfortable. You can get a free copy here

Plus, join our market newsletter for more on dividend growth investing. 

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After a year ...

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Dividend Growth: The Quiet Engine of Wealth 

Dividend growth investing sounds simple, but doing it well for decades is not. Markets get noisy. Numbers get confusing. That’s why we wrote Dividend Growth: The Quiet Engine of Wealth—a practical guide to building a framework you can stick with when things get uncomfortable. You can get a free copy here

Plus, join our market newsletter for more on dividend growth i...

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📘Free Short Book: Dividend Growth, the Quiet Engine of Wealth 

If today’s market feels noisy, this short book lays out a calmer framework. 

Dividend Growth: The Quiet Engine of Wealth explains the same principles discussed in this episode—discipline, compounding, sustainable income growth, and staying focused when markets distract. 

It’s a quick read (about 90 minutes) and walks through how dividend g...

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November 19, 2025 33 mins

How strong is your dividend growth portfolio? Send it to us for a free evaluation at dcm.team@growmydollar.com. Plus, join our market newsletter for more on dividend growth investing.

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Consumer staples look reliable with strong brands, steady cash flow, and good yields. But dividends can’t outrun revenue forever, and across this sector the growth engine has stalled.

In this episode, Greg begins with a quick recap of how ...

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How strong is your dividend growth portfolio? Send it to us for a free evaluation at dcm.team@growmydollar.com. Plus, join our market newsletter for more on dividend growth investing.

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Wall Street’s creativity knows no bounds, especially when it comes to selling safety or income. In this episode, Greg revisits Warren Buffett’s timeless wisdom to uncover who’s “swimming naked” in today’s mar...

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How strong is your dividend growth portfolio? Send it to us for a free evaluation at dcm.team@growmydollar.com. Plus, join our market newsletter for more on dividend growth investing.

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When a stock’s price is falling, its yield is sky-high, and there’s plenty of doubt, it looks like a classic value trap. Does it ever make sense for dividend growth investors to walk into that trap? Sometimes, what’s under the...

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How strong is your dividend growth portfolio? Send it to us for a free evaluation at dcm.team@growmydollar.com. Plus, join our market newsletter for more on dividend growth investing.

Dividend investing isn’t about settling for slow growth. To grow your income, you need to own growing companies, and the real wins come when you find them at a discount. The trick is seeing past the headlines and recognizing value even in busines...

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How strong is your dividend growth portfolio? Send it to us for a free evaluation at dcm.team@growmydollar.com. Plus, join our market newsletter for more on dividend growth investing. 

In what may be the largest M&A deal of 2025 so far, Union Pacific ($UNP) has made a formal bid to merge with Norfolk Southern ($NSC). The proposed merger not only furthers the consolidation of the quasi-monopolistic railroad industry but also...

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How strong is your dividend growth portfolio? Send it to us for a free evaluation at dcm.team@growmydollar.com. Plus, join our market newsletter for more on dividend growth investing. 

If you’ve ever struggled to stay disciplined in a world chasing growth or yield at all costs, this episode is for you. Whether you’re a seasoned dividend investor or new to the strategy, clarity, intention, and long-term thinking are ...

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 More on dividend growth investing  -> Join our market newsletter! 

The argument has long been made that venturing beyond America’s borders will offer investors higher yields. Many foreign companies do pay attractive dividends, but they lack consistency and predictable growth—factors that have kept us from investing overseas. 

But in this episode, we break the mold and head to the vineyards of Franc...

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More on dividend growth investing  -> Join our market newsletter!  

While dividend growth remains the core of what we do, it’s not the only path to building an income stream. In times of market distress, opportunities emerge that are simply too compelling to ignore. When venturing into troubled waters, the key is to stay disciplined and unemotional. Volatility may test you, but the potential rewards can be worth i...

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Schedule a meeting with us ->  Financial Planning & Portfolio Management 

Almost everyone knows that tariffs and trade wars have sent global markets spiraling, with the Dow down 17% and the S&P 500 down 20% from their highs, based on our recording date. While technically that implies we have entered a bear market, it also means bette...

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Schedule a meeting with us ->  Financial Planning & Portfolio Management 

After Williams Sonoma reported earnings before market open on March 19th, 2025, we saw their results as an excellent example of how to execute a dividend growth strategy on a day-to-day basis. While we have covered $WSM in several previous episodes, it is a c...

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March 15, 2025 33 mins

More on dividend growth investing  -> Join our market newsletter!  

Schedule a meeting with us ->  Financial Planning & Portfolio Management 

While it may be a somewhat misused paraphrase of Warren Buffett's famous baseball analogy, 'fat pitch' is a term often thrown around in investing circles. In most settings, it implies that an investment opportunity is extremely lucrative with a high probability of ...

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More on dividend growth investing  -> Join our market newsletter!  

Schedule a meeting with us ->  Financial Planning & Portfolio Management 

Following brief upward momentum after we first bought Hershey, the stock proceeded to slide downward. Cocoa prices remain elevated, and there is significant uncertainty surrounding the short-term impacts on the company's operations. However, Hershey's recent earnin...

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