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 follows the chain of consequences and the ripple effects most people ignore. In an era where AI can reshape an industry in months, the gap between those two ways of thinking has never been more costly to ignore.

From there, Greg walks through real portfolio positions—Intel (INTC) and Accenture (ACN)—to show how second-level thinking plays out in practice. He also runs through a handful of names—Union Pacific (UNP), UPS (UPS), GE Vernova (GEV), Chevron (CVX), Lockheed Martin (LMT), General Dynamics (GD), Johnson & Johnson (JNJ), and Merck (MRK)—to illustrate which kinds of businesses AI threatens, which ones it quietly strengthens, and why some of the most "boring" dividend stocks may be the most defensible investments of the next decade. The core argument: brands, software, and moats built on perception are vulnerable. Logistics, infrastructure, and physical production are not, and AI may actually make them stronger.

Topics Covered:

[00:41] Introduction & why AI matters for dividend investors 

[04:47] First-level vs. second-level thinking — the Howard Marks framework 

[08:43] AI is accelerating disruption — and may be technology's own worst enemy 

[11:21] Are strong brands and moats as durable as we thought? 

[13:50] Why physical infrastructure may be the best AI defense 

[15:19] Intel ($INTC) — patience, conviction, and the US chip story 

[18:16] Accenture ($ACN) — the market's fear may be first-level thinking 

[22:21] Union Pacific ($UNP), UPS ($UPS) — logistics AI can't replace 

[24:27] Rapid-fire second-level takes: GEV, CVX, LMT, GD, JNJ, MRK 

[28:08] Final takeaway: the game has changed, sustainable dividend growth requires a new lens 

Send us Fan Mail

________ 

Disclaimer: Past performance does not guarantee future results. This episode is for educational purposes only and is not investment advice.

________ 

RESOURCES:

Schedule a meeting with us: Financial Planning & Portfolio Management 

Getting into the weeds: DCM Investment Reports & Models

If you enjoy the show, we'd greatly appreciate it if you subscribe and leave a review

Follow us on:
Instagram | Facebook | LinkedIn | X

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 $535 million starting point: Republic Plaza (one of Denver’s premier office towers), Sysco ($SYY), and DCM’s own Model Portfolio. In year one, the building won on income. Today, thirteen years later, it's generating the least of the three, and the building itself has lost nearly half its value. The model portfolio, which started with the lowest income, now generates the most. The difference wasn't asset class. It was whether the income grew.

That compounding gap is what Greg calls the "second decade effect"—the point where a growing income stream laps a higher but stagnant one. It's also why income focus gives investors something price-chasing never can: control, predictability, and a reason to stay put when markets get uncomfortable.

Topics Covered:

[00:00] Introduction & the "income mailbox" reframe

[01:34] Why the word "dividend" misleads investors

[04:26] The foundation: every investment is a bet on cash flow

[06:09] Three investments, same $535 million starting point, 2013

[09:17] Thirteen years later: how each one performed

[13:59] The "second decade effect" — why growing income wins over time

[17:48] Two mindsets: growing income vs. speculating on price

[20:11] What the NYSE closing bell taught Greg about how investors think

[24:38] Dividends vs. buybacks: why income creates capital discipline

[28:42] Three takeaways and final thoughts

________ 

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. 

________ 

Send us Fan Mail

________ 

Disclaimer: Past performance does not guarantee future results. This episode is for educational purposes only and is not investment advice.

________ 

RESOURCES:

Schedule a meeting with us: Financial Planning & Portfolio Management 

Getting into the weeds: DCM Investment Reports & Models

If you enjoy the show, we'd greatly appreciate it if you subscribe and leave a review

Follow us on:
Instagram | Facebook | LinkedIn | X

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 roughly 20%, targets a complementary customer segment, and appears reasonably priced on a free cash flow basis. But it also introduces meaningful risks—rising debt, pressure on credit quality, and a near-term dividend growth story that looks very different from what it did a week ago. 

Greg walks through the numbers, the strategic rationale, and the trade-offs investors need to consider. More importantly, he tackles the core dilemma: how do you balance dividend growth discipline with total return potential when a high-quality business enters a gray area? 

Topics Covered:

[00:00:41] Overview of Sysco’s $29B acquisition

[00:02:13] Restaurant Depot’s niche and why the deal could work

[00:05:24] Valuation breakdown: Did Sysco overpay or get a fair deal?

[00:07:45] Debt impact, interest costs, and credit rating risks

[00:11:11] Deleveraging plan and what it means for financial flexibility

[00:12:18] Dividend outlook: Why growth may stall in the near term

[00:14:24] Valuation opportunity, execution track record, and upside potential

[00:15:26] The core dilemma: balancing dividend growth vs total return

________ 

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. 

Send us Fan Mail

________ 

Disclaimer: Past performance does not guarantee future results. This episode is for educational purposes only and is not investment advice.

________ 

RESOURCES:

Schedule a meeting with us: Financial Planning & Portfolio Management 

Getting into the weeds: DCM Investment Reports & Models

If you enjoy the show, we'd greatly appreciate it if you subscribe and leave a review

Follow us on:
Instagram | Facebook | LinkedIn | X

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 hidden risks behind high yields and limited liquidity, evaluate Campbell’s ($CPB) and whether its elevated dividend is sustainable amid weakening fundamentals, and revisit Chevron ($CVX) as a case study in durable, growing income during oil market volatility.

Along the way, we explore why rising yield can be a warning sign, how cash flow drives long-term returns, and what separates sustainable dividend growth from income traps.

Because when volatility rises, the goal isn’t to predict the next move. It’s to stay anchored.

Topics Covered

[00:11] Introduction

[03:31] Market Volatility & Investor Sentiment 

[04:47] Private Credit Risks & High Yield Illusion 

[11:04] Campbell’s ($CPB): High-Yield Warning Signs 

[17:17] Chevron ($CVX): Dividend Stability in Oil Volatility 

[26:38] Berkshire Hathaway: Reminder on the Importance of Cash Flow 

[29:11] The Dividend Anchor & Final Takeaways

________ 

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. 

Send us Fan Mail

________ 

Disclaimer: Past performance does not guarantee future results. This episode is for educational purposes only and is not investment advice.

________ 

RESOURCES:

Schedule a meeting with us: Financial Planning & Portfolio Management 

Getting into the weeds: DCM Investment Reports & Models

If you enjoy the show, we'd greatly appreciate it if you subscribe and leave a review

Follow us on:
Instagram | Facebook | LinkedIn | X

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. 

________ 

After a year of lagging the S&P 500, dividend investors are finally playing catch-up. Income is growing. Prices are rising. Total returns are improving.

But success brings a new challenge: what happens when valuations rise, yields fall, and future returns get harder to find?

In this episode, Greg explores the hidden downside of success in dividend growth investing. With dividend stocks outperforming early in 2026 and capital rotating out of growth and AI, he explains why rising prices create a new challenge: redeploying capital without sacrificing long-term returns. He revisits income growth vs. total return, explains why cash flow acts as the anchor in volatile markets, and walks through why sometimes the best move is to do nothing. He also contrasts chasing yield with sustainable compounding, including why shifting into Treasuries for higher income can miss the bigger picture.

The second half of the episode moves into real portfolio examples—showing what “sell,” “hold,” and “buy” look like in practice:

Why Emerson Electric ($EMR) no longer fits the model
What Clorox’s ($CLX) acquisition strategy could mean for dividend growth
How Hershey ($HSY) shows patience through commodity cycles
Why Accenture ($ACN) represents a redeployment opportunity

Long-term success isn’t about chasing what’s working today. It’s about discipline, letting income compound, and trusting that if cash flow grows, prices follow.

Topics Covered:
 
[00:11] Introduction
[03:45] Income growth vs. total return investing
[07:24] Why dividend income is the anchor
[09:52] Valuation risk and redeployment challenges
[10:22] Buffett, patience, and portfolio discipline
[11:38] Treasuries vs. dividend stocks: yield vs. growth
[13:03] Cash flow as the North Star
[15:26] Emerson Electric ($EMR): selling a winner
[20:03] Clorox ($CLX): acquisition risk and dividend sustainability
[27:40] Hershey ($HSY): commodity cycles and patience
[32:03] Accenture ($ACN): dividend growth opportunity
[35:11] Redeploying capital in rising markets
[36:07] Final takeaway: consistency and long-term compounding
 
 

Send us Fan Mail

________ 

Disclaimer: Past performance does not guarantee future results. This episode is for educational purposes only and is not investment advice.

________ 

RESOURCES:

Schedule a meeting with us: Financial Planning & Portfolio Management 

Getting into the weeds: DCM Investment Reports & Models

If you enjoy the show, we'd greatly appreciate it if you subscribe and leave a review

Follow us on:
Instagram | Facebook | LinkedIn | X

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 investing. 

________ 

If you could only look at one number to judge whether a dividend can keep growing for decades, what would it be?

In this episode, we strip investing back to first principles. Greg talks about why investors get overwhelmed with data and how focusing on the wrong metrics can quietly lead you off track. Using a simple hot dog stand analogy, he explains why familiar numbers like return on equity (ROE) and return on assets (ROA) can distort reality, especially when leverage enters the picture.

From there, he introduces return on invested capital (ROIC) and shows why it does a better job connecting business quality to long-term dividend growth. Later, Greg addresses what ROIC can’t tell you and why context always matters. 

Along the way, he walks through real-world examples, including Kraft Heinz ($KHC), Southern Company ($SO), Williams-Sonoma ($WSM), and Microsoft ($MSFT), to show how capital allocation decisions compound over time. 

[00:11] Introduction

[02:50] Information overload and the danger of focusing on the wrong numbers

[04:40] The hot dog stand: ROA vs. ROE and the role of leverage

[08:15] Why both ROA and ROE can mislead dividend investors

[09:35] Return on invested capital (ROIC) explained in plain English

[13:30] ROIC, cost of capital, and long-term value creation

[14:55] Case study: Kraft Heinz and why high yield can be a trap

[18:30] Case study: Southern Company and when low returns still “work”

[22:10] Case study: Williams-Sonoma and disciplined capital allocation

[24:55] Case study: Microsoft and the power of long-term compounding

[29:10] The limits of ROIC and why incremental returns matter

[31:25] Final takeaway: one number, long time horizons, evolving businesses

Send us Fan Mail

________ 

Disclaimer: Past performance does not guarantee future results. This episode is for educational purposes only and is not investment advice.

________ 

RESOURCES:

Schedule a meeting with us: Financial Planning & Portfolio Management 

Getting into the weeds: DCM Investment Reports & Models

If you enjoy the show, we'd greatly appreciate it if you subscribe and leave a review

Follow us on:
Instagram | Facebook | LinkedIn | X

📘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 growth works across full market cycles, including bull and bear markets. 

👉 Download the free eBook:
 growmydollar.com/dividend-growth-book 

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

________ 

Dividend growth investing can feel uncomfortable when a handful of growth stocks dominate headlines and performance. When value lags and momentum strategies seem unstoppable, it’s easy to wonder whether patience and discipline still make sense. 

To round out 2025, Greg steps back from the noise to revisit foundational principles of dividend growth investing and explain why they remain intact, even in today’s market. He walks through why distraction is one of the biggest risks investors face, how compounding quietly does the heavy lifting, and why tying income growth to long-term economic growth creates a durable framework that doesn’t depend on short-term cycles 

From the “Vitamin C” concept to classic compounding examples like the penny story and the Rule of 72, this episode reinforces how small, consistent decisions compound into meaningful income over time. Greg also revisits dividend growth targets, yield “sweet spots,” and the practical levers investors can pull to sustain income growth. The episode culminates in a real-world look at the model portfolio, which has been running since 2010. 

From all of us here at The Dividend Mailbox®, Happy Holidays!

Topics covered: 

00:00 – Introduction and why this is a good time to revisit first principles 

01:10 – Market distractions, information overload, and staying focused 

03:20 – Introducing the new book: Dividend Growth: The Quiet Engine of Wealth 

04:20 – The “Vitamin C” concept and daily discipline 

05:40 – The penny story and how compounding really works 

09:40 – The Rule of 72 and the long-term cost of short-term decisions 

11:10 – “The line”: GDP growth, earnings growth, and dividend growth 

14:30 – Targeting 7% dividend income growth 

16:30 – The 2–4% dividend yield sweet spot 

17:55 – Income growth levers: reinvesting, reallocating, and dividend increases 

20:40 – The Model Portfolio story and track record

26:40 – Final thoughts on discipline, sustainability, and staying the course 

Have questions or want a second opinion on your dividend strategy?
Email us anytime at [email protected] for a free portfolio review and ongoing dividend insights. 

Send us Fan Mail

________ 

Disclaimer: Past performance does not guarantee future results. This episode is for educational purposes only and is not investment advice.

________ 

RESOURCES:

Schedule a meeting with us: Financial Planning & Portfolio Management 

Getting into the weeds: DCM Investment Reports & Models

If you enjoy the show, we'd greatly appreciate it if you subscribe and leave a review

Follow us on:
Instagram | Facebook | LinkedIn | X

How strong is your dividend growth portfolio? Send it to us for a free evaluation at [email protected]. Plus, join our market newsletter for more on dividend growth investing.

________

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 2025 has unfolded so far, highlighting strong income growth for the model portfolio, a handful of growth names driving market performance, and value strategies continuing to lag. From that backdrop, he digs into the disconnect between the appearance of safety in consumer staples and the underlying fundamentals that truly support dividend growth. 

Using Kimberly-Clark ($KMB), General Mills ($GIS), Colgate ($CL), Procter & Gamble ($PG), and Church & Dwight ($CHD) as case studies, Greg shows how companies with high ROIC and defensive business models can still become no-growth traps. These companies were once consistent outperformers with impressive dividend histories, but the economy evolves and so have their growth profiles.

Topics Covered:

03:05 – Comparing dividend growth to the S&P 500

05:43 – Investing styles cycle and chasing rarely works

07:07 – Surface numbers can be misleading

11:00 – Kimberly-Clark: attractive metrics masking zero growth

16:42 – General Mills: high yield but barely growing

18:36 – Colgate: excellent margins, slow dividend progression

19:58 – Procter & Gamble: financial strength, but limited growth

21:03 – Church & Dwight: a past outlier that doesn’t meet our targets

23:57 – Kimberly-Clark’s planned Kenvue acquisition

29:36 – The mosaic of evidence investors should pay attention to

Have questions or want a second opinion on your dividend strategy?
Email us anytime at [email protected] for a free portfolio review and ongoing dividend insights.

Send us Fan Mail

________ 

Disclaimer: Past performance does not guarantee future results. This episode is for educational purposes only and is not investment advice.

________ 

RESOURCES:

Schedule a meeting with us: Financial Planning & Portfolio Management 

Getting into the weeds: DCM Investment Reports & Models

If you enjoy the show, we'd greatly appreciate it if you subscribe and leave a review

Follow us on:
Instagram | Facebook | LinkedIn | X

How strong is your dividend growth portfolio? Send it to us for a free evaluation at [email protected]. Plus, join our market newsletter for more on dividend growth investing.

________

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 market. 

Drawing on Rob Arnott and Edward McQuarrie’s recent CFA research on risk and investor psychology, he explains how both fear of loss and fear of missing out drive market behavior far more than models admit. Greg dissects several headline-grabbing products, from “high income” S&P 500 ETFs and 77% yielding Nvidia options funds to the Dual Directional Buffer ETF and the “Magnificent Seven Snowball,” revealing how they offer the illusion of safety or income while eroding long-term returns. He closes with a Buffett-style case study on Occidental Petroleum and Berkshire Hathaway’s recent deal, underscoring the power of simple, steady cash flow over engineered complexity.

As Leonardo da Vinci said, “Simplicity is the ultimate sophistication,” and it is also one of the surest ways to compound wealth.

Topics Covered

[00:00:41] – Who’s swimming naked? The illusion of risk-free returns
 [00:02:31] – Understanding risk and fear in markets: Rob Arnott’s research
 [00:06:22] – How fear of loss and FOMO distort risk premiums
 [00:09:19] – The rise of high-income ETFs: chasing yield in disguise
 [00:12:32] – The Nvidia ($NVDA) income strategy ETF: 77% yield, but at what cost?
 [00:16:09] – Dual Directional Buffer ETF: the illusion of protection
 [00:21:14] – The “Mag 7 Snowball” structured note: Wall Street’s creative packaging
 [00:25:47] – Why these structures guarantee Wall Street wins
 [00:26:45] – Buffett, Occidental ($OXY), and the value of consistent cash flow
 [00:32:20] – Simplicity, cash flow, and the sophistication of staying patient

For more on dividend growth investing or to request a free portfolio review, email [email protected].

 Past performance does not guarantee future results. This episode is for educational purposes only and is not investment advice.

Send us Fan Mail

________ 

Disclaimer: Past performance does not guarantee future results. This episode is for educational purposes only and is not investment advice.

________ 

RESOURCES:

Schedule a meeting with us: Financial Planning & Portfolio Management 

Getting into the weeds: DCM Investment Reports & Models

If you enjoy the show, we'd greatly appreciate it if you subscribe and leave a review

Follow us on:
Instagram | Facebook | LinkedIn | X

How strong is your dividend growth portfolio? Send it to us for a free evaluation at [email protected]. Plus, join our market newsletter for more on dividend growth investing.

________

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 hood tells a very different story.

In Episode 51, Greg revisits UPS ($UPS), a company we last covered years ago but is now back on our radar for entirely new reasons. Rising wages, Amazon contract changes, and global trade tariffs have cut the stock price in half since 2022, sending its dividend yield toward 8%. At first glance, it looks like the market is pricing it for a dividend cut.

But step behind the headlines, and the story gets more compelling: UPS continues to post solid margins, generates strong cash flow, and has the scale and efficiency to remain a leader in global logistics. Even if a dividend cut occurs, investors may still come out ahead with sustainable yields and renewed dividend growth potential. Greg breaks down the scenarios, risks, and catalysts that make UPS a compelling story to consider.

Topics Covered:

•  [00:03:32] Why UPS looks like a high-yield “problem child” but may still be a dividend growth play
• [00:06:20] UPS’s history: growth in revenue, profits, and dividends since 1999
• [00:09:58] The “trifecta” of headwinds—union wage hikes, Amazon contract cuts, and tariffs
• [00:12:36] Comparing UPS vs. FedEx ($FDX), Amazon ($AMZN), USPS, and DHL in market share and profitability
• [00:19:57] How AI could improve delivery efficiency
• [00:21:12] Business metrics, profitability, debt profile, and why UPS’s financing signals investor confidence
• [00:25:27] The dividend dilemma: can UPS sustain its payout, or is a cut coming?
• [00:27:44] Three scenarios: steady dividend, improved valuation, or a cut that resets growth
• [00:31:47] Long-term catalysts: tariffs, Amazon shifts, and global trade recovery
• [00:33:37] What research firms (Morningstar, Value Line) are projecting for UPS
• [00:34:56] Final take: UPS as a value play that still pays you to wait

Send us Fan Mail

________ 

Disclaimer: Past performance does not guarantee future results. This episode is for educational purposes only and is not investment advice.

________ 

RESOURCES:

Schedule a meeting with us: Financial Planning & Portfolio Management 

Getting into the weeds: DCM Investment Reports & Models

If you enjoy the show, we'd greatly appreciate it if you subscribe and leave a review

Follow us on:
Instagram | Facebook | LinkedIn | X