158 - I Asked AI to Pick Dividend Stocks And It Blew My Mind

Can AI explain dividend growth investing better than most investors?

In this episode, we put AI to the test by asking it to compare dividend growth stocks across three categories: low yield, mid yield, and high yield. The goal was simple: show what happens to a hypothetical $10,000 investment over 10 years when dividends are reinvested and companies keep growing their payouts.

What came back was more interesting than expected.

This episode breaks down the difference between current dividend yield and yield on cost, why dividend growth can matter more than starting yield, and how DRIP compounding changes the math over time.

We also talk about one of the biggest traps in dividend investing: assuming a 5%+ yield automatically beats a 1%–2% yield. Sometimes it does—especially if you need income now. But if you have a 10+ year runway, the boring dividend grower with faster payout growth can quietly become the monster.

In this episode, we cover:

• AI’s dividend growth stock experiment
• What yield on cost actually means
• Why low-yield dividend growers can outperform over time
• The difference between income now vs wealth-building later
• Why the 10–20 year dividend growth streak may be the sweet spot
• How DRIP changes share count, income, and long-term results
• The problem with chasing high yield without looking at growth
• How to prompt AI better so you don’t get vague, messy, or overstuffed answers

This is part dividend lesson, part AI experiment, and part reminder that compounding is usually boring… until it gets ridiculous.

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DISCLAIMER Ticker metrics change as markets and companies change, so always do your own research. The content in this podcast is based on personal experience and is for educational purposes, not financial advice. See full disclaimer here.

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