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

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

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RESOURCES:

Schedule a meeting with us: Financial Planning & Portfolio Management

Getting into the weeds: DCM Investment Reports & Models

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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 $535 million starting point: Republic Plaza (one of Denver’s premier office towers), Sysco ($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

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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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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

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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 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