Dear Financial Samurais,
Every Fourth of July weekend, I like to take a moment to reflect on where I stand on the freedom meter. Am I doing things that increase my freedom, or am I slowly giving it away?
This year, I decided to stay with my parents in Honolulu—a choice that came with restrictions I haven't experienced in decades. Things like: which side of the sink I'm allowed to cut fruit, how long leftovers can stay in the fridge, and even where I’m supposed to place my toothbrush on the counter.
Living under someone else’s roof means playing by their rules, and it reminded me just how much freedom I’ve had since leaving for college. If you ever find yourself taking your independence for granted, try staying with your parents or relatives for more than a week. It’ll recalibrate your appreciation real quick.
Since arriving on June 15, I’ve felt a renewed urgency to save and invest more aggressively, with the goal of affording a rental house next year. I’ve also spent over 15 hours and a good chunk of money rehabbing a neglected in-law unit, so we have a more comfortable place to stay next time.
Once you lose your freedom, you'll do everything you can to get it back. Oh, how I miss having an en suite bathroom and a Toto Washlet!
The U.S. Has Outperformed the U.K.
Ever since the 13 American colonies declared independence from Great Britain on July 4, 1776, the U.S. has steadily pulled ahead in terms of GDP per capita. While many factors play into this, it’s hard not to credit the entrepreneurial fire that freedom ignites. Once you're free, you're more motivated to build, grow, and make something of yourself—especially after the ashes of World War II.
As I dug into the data on where millionaires are migrating around the world and why, one country stood out: the U.K. It’s been hemorrhaging millionaires at the fastest rate—especially when adjusted for population size. Why? Punitive tax policies are driving out the wealthiest citizens.
Lawmakers everywhere should be careful. Raise taxes too aggressively on the group already paying the most, and you might end up with less total revenue and fewer businesses. In the U.S., for example, the top 1% earn about 22% of total income but pay roughly 41% of all federal income taxes. For many who don't pay as much in taxes, this is still not enough.
Check out: Millionaire Migrations: Where Millionaires Are Moving Globally
Mustering Up the Courage to Invest Can Be Hard
After the S&P 500 crossed 6,000, my interest in buying more began to fade. On one hand, I was skeptical of the rally’s sustainability. On the other, I was optimistic about the second half of the year due to potential tax cuts and deregulation.
Whenever I feel conflicted—knowing I should invest but don’t want to—I fall back on the dumbbell investing strategy. I’ve been using this approach since 2000, after witnessing the dot-com bust wipe out so many investors. That painful crash solidified my love for real estate, and the value of investing on both ends of the risk spectrum.
In this latest move, I allocated $100,000 to ~4.4%-yielding Treasury bills for safety, and another $100,000 to Fundrise Venture for upside exposure to private AI companies. AI is driving the next wave of innovation and I want in. At the same time, I’m still working to rebuild my passive income stream after buying my current home.
I don't know about you, but every dollar I invest makes me feel calmer and more hopeful about the future. Given the choice, I’d much rather put $200,000 into investments than spend it on a new Range Rover Sport for $120,000, four first-class tickets to Hawaii, and a month-long vacation rental. Although… that actually sounds pretty great, nothing beats the feeling of freedom and financial security.
What’s also encouraging is knowing that thousands of highly motivated, smart, and idealistic people are working at these private startups—many of which we can now invest in—to potentially help us build wealth.
If you’re feeling caught between fear and FOMO, the dumbbell investing strategy might be the tool you need to move forward with clarity and confidence.
See: The Dumbbell Investing Strategy: Balancing Risk and Safety
Taxes and Lifestyle
Next week, I’ll be breaking down the One Big Beautiful Bill Act (OBBBA) and how it actually helps those on the path to financial independence—without getting my head chewed off in the process. I’ll also share some sacrifices worth considering if you want to live a richer, freer lifestyle.
As of today, I’m three weeks into our five-week, one-day trip to Honolulu. And I’ll be candid—it hasn’t been all sunshine and rainbows. But the biggest lesson I’ve learned is this:
Freedom doesn’t just happen. You have to fight for it every single day.
To Your Financial Freedom,
Sam
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