Apple, my top individual holding — and one of the most disappointing performers YTD — just decided to bend the knee to Trump, announcing another $100 billion to expand its operations in the U.S. I'm glad Apple is reinvesting some of its cash flow and huge balance sheet back into America. However, I’m still not sure how Apple plans to invest a total of $600 billion domestically over the next four years while also hiring 20,000 U.S.-based workers. But the announcement has at least bought it a reprieve from tariffs.
Due to Apple’s oligopoly — some might even say monopoly — we’ve seen a lack of true innovation in its products for years. When you’re already printing extraordinary profits, the incentive to disrupt yourself isn’t exactly strong. However, with courts cracking down on the company’s high take rate for App Store listings and its lucrative deal with Google to remain the default browser, Apple is being forced to rethink its strategy.
Now, by sidestepping tariffs while competitors get hit, Apple has found a new asymmetric way to profit. Wall Street has taken note as analysts are bumping their target prices for Apple by 4%–10%, to the $250–$270/share range.
What Are You Willing To Do To Get Ahead?
This whole episode is a reminder that everyone bends the knee at some point to make money, survive, and thrive. CEO Tim Cook is beholden to shareholders, and he must deliver or else be dismissed. You might completely disagree with your boss, but unless you’re prepared to get passed over and lose income, you’ll probably have to conform. The lucky ones find the right cultural fit, where values align and career advancement comes naturally.
I remember having to bite my tongue more times than I’d like while working in finance. But once I hit my target net worth, I negotiated a severance to escape the corporate politics altogether. While I may technically be “poorer” for leaving, my soul is wealthier — free to live and act entirely in accordance with my own values.
Suffering From Intense FOMO Since Coming Back
If you want to experience less FOMO, don’t live in a hyper-competitive city like San Francisco or New York, where everyone is clawing to get ahead and make a fortune. In Honolulu, my biggest concern was finding the sweetest lychee or Pirie mango in Chinatown (ABC Market). Back in San Francisco, my mind instantly shifted to how can I possibly make more money in the AI boom?
The recent Figma IPO didn’t help. Retail investors were thrown into the “Hunger Games” for allocations, just like in my banking days when we’d bring a hot IPO to market. Some investors couldn’t even get 1-on-1 time with management, instead settling for a rubber chicken group lunch.
And who got the biggest allocations? The largest clients paying the most fees. When those IPOs popped, they made the most money, which led them to do even more business with the bookrunners.
That’s how the system works, folks: the rich and connected tend to get richer and more connected. If you’re not either, you have to hustle, network, and bring value to others, or accept falling further behind.
Read next: The Futility Of Chasing A Hot IPO And What To Do Instead
A Conversation With Ben Miller, CEO of Fundrise, About AI Growth
In my first week back, I met up with Ben Miller for lunch while he was in town. I finally put together my recap post from our podcast conversation about what he’s seeing in AI. Listen and read here: The Acceleration Of AI Growth.
It’s worth paying close attention – this train is leaving the station. Back in 2000 during the first dot-com frenzy, when I had little money, I told myself that if I ever had another opportunity like that, I’d invest more aggressively. Bitcoin never convinced me to go all-in due to its questionable use cases, but with AI, I’m witnessing the impact in real time—my dad lost his editing job, and traffic from Google search is harder than ever to get.
Sooner or later, AI will come for your job. The only real ways to protect yourself: become an AI product expert and invest in AI.
If you’re a parent willing to spend a fortune sending your kids to college only for them to graduate jobless, you should at least consider investing in the very technology shaping (and potentially shrinking) their job market.
Preparing for Rate Cuts
Looking ahead, it’s worth considering how interest rate cuts could ripple through our investments. The real estate market is clearly in a summer lull, but the spread between mortgage rates and Treasury yields is narrowing meaningfully.
There’s growing anticipation for two Fed rate cuts by year-end—some analysts are even floating the possibility of three or four. If they go that far, it would signal the Fed is behind the curve and the economy is weaker than expected.
It’s important to remember: the Fed doesn’t directly control mortgage rates—the bond market does. That said, the mere expectation of cuts can spark renewed activity in real estate. On the other hand, too many cuts too quickly could unsettle public equity investors instead of encouraging them.
After three years of real estate underperformance relative to equities, the tide may finally be ready to turn. The mantra “survive until 2025” has been a rallying cry for commercial real estate investors, and for the most part, the sector has survived. Now, the window to thrive again may be opening, especially if Fed rate cuts follow the above path for the next 17 months.
Investing in both commercial real estate and AI companies is a type of dumbbell approach to investing. The first is a deep value turnaround story. The other is a high growth momentum story. Both can be invested in through Fundrise, a long-time sponsor where I've invested over $400,000 with the platform.
In my latest real estate post, I revisit the tax-free home sale exclusion rule. Many people misunderstand how to actually use it to save money on taxes when selling a property—especially when a property has been rented out part of the time. To clear things up, I’ve put together three straightforward examples showing how to pro-rate the tax-free exclusion on your profits when you’ve had rental use.
See: How To Use The Tax-Free Exclusion Amount Every Two Years To Save
The Upcoming Weeks
For the remaining two out of three weeks, I’ll be running “Daddy Summer Camp” until school starts again. It’s funny how my kids will listen to a coach or teacher without question, yet treat my instructions in defiance. Still, the effort to teach them tennis and pickleball is worth it, otherwise, I might as well get a job.
I’ve got plenty of fun and thought-provoking topics lined up on Financial Samurai, so stay tuned. And if there’s a particular topic you’d like me to explore, don’t hesitate to share your ideas.
To Your Financial Freedom,
Sam
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