How Uncle Sam + ChatGPT = 9% and 12% Dividends

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A nifty dividend duo—with yields of 9% and 12%—is ready for takeoff. Thanks to Uncle Sam’s spending bender coinciding with the rise of the machines.

Big tech stocks are about to remind Wall Street why it fell in love with these shares in the first place. Think you’ve seen a tech bubble before? Just wait until tech firms report earnings later this month!

These companies are growing sales and profits by deploying robots instead of hiring humans. Their AI-driven tools are faster, more scalable, and much cheaper than carbon-based labor. Cost savings are dropping straight to tech bottom lines.

Expect proof of trend as the Nasdaq’s increasingly machine-driven companies report banner earnings in the coming weeks.… Read more

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Big companies are about to make even more money. They have discovered they no longer need armies of new hires to grow—extremely bullish news for shareholders because human employees are expensive.

Good ones can also be notoriously elusive. For example, I’m the longest-standing member of my kids’ school marketing committee, and we’re always scrambling for volunteers (what non-profit isn’t?).

Until now, that is.

Over the weekend, we welcomed the most talented marketer I’ve ever worked with to our team: ChatGPT 4.5. “GPT” graciously accepted our volunteer position, and we’re already actively boosting online referrals for the school. I’m learning cutting-edge “AI referral” techniques straight from the entity that invented them.… Read more

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If the April lows hold, the S&P 500 will clock a 19% peak to trough drop on the tariff news. The drawdown could have been worse—if the bond market had not broken!

President Trump was initially resolute in the face of a declining stock market. Wall Street was desperately, unsuccessfully searching for a “Trump Put”—a save from the decline by the White House. Trump, however, likened the levies to a necessary remedy:

“Sometimes you have to take medicine.”

Treasury Secretary Scott Bessent, meanwhile, must have silenced his phone for a few weeks while his old Wall Street contacts texted and texted (and called) and texted.… Read more

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Many of you have written in asking about DeepSeek’s latest release and its potential effects on our income portfolio and strategies. Let’s discuss the latest in AI because, yes, there are ripples into Dividendland that are not fully appreciated by mainstream investors.

(And tariff questions, we’ll get to you in the coming weeks!)

First the DeepSeek disruption in AI, and let’s take vanilla dividend darling Nasdaq 100 Covered Call ETF (QYLD), which yields 12.2% as our example. Is that big divvie still safe and secure? Income seekers are constantly staring at the fund, writing in to ask me if they have permission to:

  1. Buy QYLD.

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I had just spent my whole paycheck at Whole Foods. My wife was not amused.

“Brett,” she paused and trailed off, a telltale sign that I was in the hot seat.

“You don’t have to buy everything organic. Some stuff…” she searched for words, shaking her head.

I flailed for a life raft: “But isn’t organic good?”

“Some fruits, sure,” she conceded. “And vegetables. But not all of them. Like avocados, and bananas—they have thick skins, so it really doesn’t matter if they are organic or not.”

“And cookies. Cookies are a highly processed food. Why are you bothering with organic?”… Read more

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