Dear Financial Samurais,
The May CPI came in lower than expected at +0.1% MoM and +2.4% YoY, with core inflation at +2.8%. These are relatively benign figures, especially considering May was the first full month potentially impacted by the tariff debacle.
The cooler inflation data has revived expectations for two Fed rate cuts. Unfortunately, renewed conflict between Iran and Israel has pushed oil prices higher and triggered broad risk-off sentiment across markets.
Strangely, instead of a flight to safety, both stocks and bonds sold off. This is yet another example why I prefer owning individual Treasury bonds to maturity rather than bond funds that can whipsaw in times of stress.
Iran has declared that Israel and the U.S. will “pay,” and sadly, I don’t doubt that something bad may happen.
Here’s a great reminder in chart form: on the journey to financial independence, the most important rule is don’t blow yourself up. A major setback can make the road to recovery long and difficult. The older I get, the more I appreciate slow and steady returns with income.
When You Know You Have Enough Money
Hot off my recent post on the risks of focusing too much on risk-free passive income, a reader asked a classic question: How do you know when you have enough money? And when should you stop chasing excess returns and focus on preserving what you have?
I love this question because the answer is so personal. But I've come up with two logical responses:
- You have enough when you’re able to take action to fix a suboptimal situation without financial worry.
- You know it’s time to shift when you can ring-fence a portion of your wealth to sustain your lifestyle for life.
I’m confident in these answers because I’ve gone through the journey myself. But due to fear and greed, most people still won’t follow what I suggest in the post. Will you?
Check out: The Best Way To Determine If You Have Enough Money
My Tremendous Mistake That I Hope Saves You Money
I’ve been sitting on this story for a couple of months to let the emotions settle. Emotion may fuel compelling writing, but it can cloud judgment.
Automation, when done right, is a powerful tool. Auto-investing every two weeks has helped me stay consistent for over 26 years. Automatic credit card payments have saved me from late fees. Overall, automation has boosted my net worth and simplified my financial life. I'm sure it has for you too.
But automation also has a dark side if you don’t stay vigilant. You can end up overpaying significantly over time, as I did.
Check out: A Terrible Life Insurance Mistake That Cost Me A Fortune. I am both disappointed in myself and in USAA, my insurance carrier for the last 23 years. But that's life. I hope by reading my story you will avoid my same fate.
What surprised me in the comments was how almost nobody shared their own financial missteps. Most claimed they review their statements monthly to catch any errors. Good! This is another reminder why I worry less about people’s finances nowadays—most folks seem to be doing just fine. Stayed tuned for a post about this topic.
If you have debt and dependents, getting life insurance is one of the most loving and responsible things you can do. I recommend checking out Policygenius—an insurance marketplace I’ve trusted for over 10 years. Enter your needs, and they’ll match you with top-rated carriers at competitive rates. Both my wife and I got matching 20-year term policies during the pandemic at a very affordable rate.
AI Investing Interest Continues to Grow
Last week I mentioned signs of a reacceleration in AI. Then Facebook dropped $14.3 billion for a 49% stake in Scale AI, a company founded in 2016 with just 1,500 employees. This is only the beginning. The AI race will continue to mint thousands of new millionaires.
CNBC also released its “Disruptor 50 list for 2025,” now in its 13th year. The list highlights the most innovative private companies, and as expected, most are focused on AI. What I found shocking is that Fundrise Venture owns the top six companies on the list, which means I do too as an investor.
So for now, I’m feeling very little FOMO. The only constraint I have is how much I can earn to invest even more before higher valuation funding rounds occur. Fundrise is a long-time sponsor of Financial Samurai and I've got ~$187,000 invested in Fundrise Venture so far.
For example, The Information is reporting that Ramp (#6 on the list, a corporate credit card company) is looking to raise at a $16 billion valuation, after raising at a $13 billion valuation on March 3, 2025. I'm not sure why Ramp would raise again so soon. But again, it sure seems like risk appetite for private growth companies is increasing.
Chime Financial’s successful IPO last week is an encouraging signal for other private companies eyeing the public markets. It priced at $27 and is now trading at $34.79, giving it a market cap of $11.56 billion. CoreWeave and Circle Internet Group were also recent standout IPOs, further validating investor appetite for high-growth tech names.
I expect similar enthusiasm for companies on CNBC’s Disruptor 50 list. But instead of waiting for the IPO pop, I’d rather get in before these companies go public to potentially capture even more upside.
Being A Dad
Mothers rightfully receive most of the praise—pregnancy, childbirth, and often the bulk of child-rearing is no easy feat.
But this Father’s Day, I wanted to share my final post reflecting on the journey of being a stay-at-home dad. After eight years and two months, I’m officially retiring from the SAHD role. Time flew by, and I feel a real sadness knowing those early years are now behind me.
For any men considering this path, let me offer some hard truths before you leap. Being a stay-at-home dad may be harder than being a stay-at-home mom, largely due to lingering societal expectations. You’ll need to wrestle with your pride and ego to do what I believe is the most important job in the world.
I gave up chasing money and meetings five years before I had kids. So once they arrived, there was no way I was going back to that world. If you’re itching to take the road less traveled, check out: Mommies, Nannies, Au Pairs, and Me.
The Long Trip Begins
I'm heading to Oahu this morning and will be offline for a bit. Looking forward to hitting some tennis and pickleballs with those of you who reached out! I will be all-out focused on fitness again this summer.
Funny enough, I’m running into the same challenge here in San Francisco—finding people in Honolulu to hit with during the day while the kids are in school. After pickup, I want to spend as much time with them as I can until bedtime.
Aloha,
Sam
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