My Portfolio Is Officially CRASHING
PRESENTED BY SNOWBALL ANALYTICS
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Well my friends, it’s official.
After being up 8% at one point here in 2025, my portfolio has now officially given back all of this year’s gains—and then some.
At the time I’m writing this, my portfolio is down 8.5% just in April alone, which leaves me down about 4.8% so far for the year. Fortunately, we’re still ahead of the rest of the market, so it could be worse.
Source: Snowball Analytics
Nonetheless, I think this might be the biggest drop my portfolio has ever seen—at least since I started investing seriously back in 2020—and it reminds me of the double-edged sword that comes with dividend investing.
On one hand, it’s totally understandable to be concerned when share prices start falling—especially this much, this fast. It feels like you’re watching your wealth evaporate in real time, and that’s not exactly a great feeling.
I’d be lying if I said I wasn’t feeling it myself right now. Not too bad, but it’s definitely there.
There are quite a few stocks in my portfolio that are getting battered beyond belief (looking at you, SBUX and WSM). But with that said, it’s important to take a step back and remember that there’s another, brighter side to all of this.
While it definitely sucks to see your portfolio value going down, that’s not the only thing that matters to us dividend investors. At the end of the day, what we’re really after is the cash flow.
The whole point of building up your collection of dividend-paying stocks is to create a consistent (and growing) stream of passive income.
In other words, the dividend is the prize. And the beauty of this seemingly sour situation is that when prices drop, the income you’re buying gets cheaper, and the return on your investment goes up.
So even though the market right now is full of fear and uncertainty, it’s also full of opportunity—especially for dividend investors. If you can look past the noise of today and stay focused on the riches of tomorrow, now is your chance to lock in higher yields and speed up the growth of your future cash flow.
That’s how I’m thinking about things right now. Even though I have no idea what the market is going to do from here, keeping this double-edged sword in mind is what’s helping me keep a cool head in this crazy market.
With that in mind, I started putting my money to work in a few stocks that I think are looking like better buying opportunities than they have in a long time. I’m telling you about those here.
Also, I want to hear from you: What good buying opportunities are you taking advantage of in your portfolio right now? Write to me here and let me know.
Dividend Investing Democratized
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IN MY PORTFOLIO 📈
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ICYMI 🎥
Our Portfolios Are DROPPING FAST | Ep. 13
In this special live-stream episode of The Deep End, Ari and I chat about our recent hangout in Vegas and share where things stand with our portfolios right now.
CAREFULLY CURATED 🔍
📺 Dividends Debunked - Dividend investing tends to catch a bit of flak, but I honestly think most of it comes from a misunderstanding of how it really works. Fortunately, Dividend Data clears the air in this video by debunking three of the most common myths around dividend investing.
🎧 Fueling Convenience - Not only is Casey’s General Store (CASY) the 3rd largest convenience store chain in the U.S. (and the 5th largest pizza chain), but it’s also a sneakily strong dividend growth stock that flies under most investors’ radars. This episode of the Business Breakdowns podcast gives you the inside scoop—and if you’re anything like me, you’ll probably want to add CASY to your watchlist after listening.
📚 Making Money Isn't Lucky - An oldie but a goodie from Naval, who says making money isn’t about luck—it’s about becoming the kind of person who makes money.
SINCE YOU ASKED 💬
"What would be your strategy if you were just starting out at age 45?"
- Gabe | YouTube
This is a really good question, and it's one I get pretty often from people who are a little closer to retirement than I am.
I’m only 31 years old, so naturally, a lot of the content I put out comes from the perspective of someone who still has a lot of time on his side. But even so, this question comes up enough that I’ve spent quite a bit of time thinking about it.
Now you might assume that someone in their 40s or 50s would need to approach investing completely differently than someone in their 20s or 30s. But in a lot of ways, the core strategy really doesn’t change all that much.
Whether you’re just getting started at 25 or 45, the goal is still the same: to build a portfolio of growing companies—or ETFs comprised of growing companies—that can consistently pay and grow their dividends over time.
In other words, the whole point is to build a stable and growing stream of passive income that can support you down the road. And the way to do that—which is by investing in growing, cash-flowing businesses—doesn’t change based on your age.
With that said, time is still one of the most important variables in the entire investing equation. And that’s where we start to see a key difference.
Someone who starts investing in their 20s has a couple extra decades of compounding working in their favor and might only need to invest $250 a month to end up with $1 million by age 65. But if you’re starting at 45, you’d need to invest closer to $1,700 a month to reach that same number by the same age.
To me, this just speaks to how powerful time really is. It's also a good reminder that there’s no shortcut to reaching financial freedom.
You can’t make up for lost time by chasing risky, speculative, high-yield stocks or ETFs. Doing so might feel like a way to get ahead, but more often than not, it ends up just setting you back.
And I understand how all of this might sound a little overwhelming—and honestly, it can be. But it’s important to remember that starting later doesn’t mean you've missed your chance to build something meaningful. You still have plenty of time on your side, and investing is an infinite game that you can play for the rest of your life.
Even if you start at 45 and plan to retire at 65, your portfolio doesn’t just stop growing the day you stop working. If you’re healthy, you could have another 25 or 30 years of compounding ahead of you—if not more. That’s a lot of time to see your investments continue compounding.
Overall, the earlier you start, the better. But even if you’re getting started later in life, the fundamentals don’t change. The game is still the same—you’re just working with a slightly different clock.
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