Dear Financial Samurai,
I’m back in San Francisco after 36 days in Honolulu, and surprisingly, I’m feeling more sad than happy. I miss the small moments with my dad—like our quiet 4:30 a.m. chats in the living room, reminiscing and talking about random things. He’s always up early to catch the market open at 3:30 a.m. HST.
This lingering melancholy reminds me that being with family is far more rewarding than living in a luxurious home. I’d happily sleep on a sofa bed in the living room if it meant I could spend more time with them.
If your parents are still alive and still live in your childhood home, I encourage you to return for an extended visit. It’s a chance to reset expectations, potentially heal old wounds, learn more about them, and better plan for both of your futures.
Check out: The Healing Power Of Returning To Your Childhood Home
Better Than a Sofa Bed in Their Home
After some time observing and soul-searching, I rolled up my sleeves to rehab a completely rundown two-bedroom, two-bath in-law unit attached to my parents' house. Even though I’ll still be sleeping on a sofa bed when we visit, at least next time, it’ll be in my own living room instead of theirs.
The unit belonged to my aunt, who sadly passed away in 2020. But she hadn’t lived there since 2013, so the place had been slowly deteriorating. Before this year, I’d never even been inside. It was the forbidden zone. But my aunt left the unit to my dad, and this time, I finally got his blessing to bring it back to life.
The process reminded me just how much I dislike remodeling. To all the financial independence seekers under 45: get your sweat equity in while you still have the motivation! The older you get, the less you'll want to deal with demo, dust, and delays. And with today’s sky-high costs, remodeling has squeezed out most—if not all—of the profit investors used to count on.
Mark my words: avoid major remodels unless absolutely necessary. Don’t do them hoping to make a profit—unless you’re significantly expanding the livable space.
Check out: The Cost To Remodel A Rundown Two-Bedroom In-Law Unit
June 2025 Median Home Price Reaches Record High
The median price for an existing home sold last month hit a record $435,300, surpassing the previous high set in June 2024, according to the National Association of Realtors. Yet, despite the price jump, overall home sales fell to a nine-month low on a seasonally adjusted basis, down 2.7% from the prior month.
It’s a fascinating dynamic. While 30 of the 50 largest metro areas are seeing price declines—especially in Washington, D.C.; Austin, Texas; and San Diego—other segments are showing surprising strength.
So where's the strength? Homes priced above $1 million, which saw a 14% increase in sales compared to a year earlier. Meanwhile, Redfin reports that nearly 29% of all buyers are paying in cash, sidestepping the impact of higher mortgage rates entirely.
With stocks, real estate, Bitcoin, and so many other asset classes at record highs, it's understandable not to rush cutting rates. But when we do, it's logical to assume incremental cash will shift toward risk assets.
The Wealth of “Enough”
You know the old saying, “I’m rich because I have enough.” We all try to be content with enough. But most of us fall short, which is why we stay in jobs we dislike or take on excessive risk. Even after I left my job in 2012, I still wanted returns above inflation—for security, out of fear, or simply because I wanted more.
So when I saw the 2025 Charles Schwab Survey results, I was shocked: the 2,200 respondents said they needed $200,000 less to feel rich compared to just a year ago! That makes no sense on the surface, especially with inflation still climbing.
Naturally, I had to dig in and explore how this could possibly be true. Spoiler: I don’t buy it.
Check out: What It Takes To Feel Wealthy Today Is Less Than Before
Why It's Harder To Be Content In A Big City
My first few days back in San Francisco were a whirlwind.
I’d forgotten I’d tentatively agreed to a dinner with a friend and some guests the day after I got back. But I was fighting a bug and too tired to make it, so I had to take a rain check. Sorry Harry.
The next day, I had lunch with Ben Miller, CEO of Fundrise. He was in town meeting with a dozen private companies—including several Fundrise Venture portfolio companies. Hearing about the momentum in private markets triggered a serious case of FOMO. For a moment, I thought about trying to join a private AI company again to make more money I don't really need.
Ben picked up the tab and enthusiastically showed me his Ramp corporate card. Fundrise Venture invested in Ramp earlier this year at a $13 billion valuation. I’d used a virtual version of the card last year and didn't understand what all the fuss was about. As soon as he paid, he got a text with the transaction, snapped a photo of the receipt, and boom—his expense report was done.
It reminded me of my old AMEX corporate card days: hoarding paper receipts, giving them to my assistant, who then had to tape them to paper, manually enter every detail, and submit it all. What a different world.
Now, Ramp is reportedly raising at a $21 billion valuation just one month after raising at $16 billion in June 2025, led by Founders Fund. Revenue is exceeding expectations.
More Business And Activity
The day after that was lunch with a serial entrepreneur friend who’s launching his own pickleball brand. He contacted manufacturers in China who make balls for the major brands. His cost? $0.59 per ball. He will sell three-packs for $10.99—a small discount to competitors. He said 500 million pickleballs are sold in the U.S. a year and he just wants 1% of the market. Naturally, I started thinking, “Why don’t I do that too?”
After lunch, we played pickleball and tested out his new ball. Not bad!
Then came a financial consultation with a woman and her husband, who so happened to be a renowned NYC-based chef. I had no idea before the call, but he invited me and my wife to be his guest, so I referred my sister and her boyfriend instead, since they live there. Then it was off to prepping a rental unit for a Saturday showing. Then poker night with the dads until 2 a.m, right before this newsletter goes out.
In other words, if you truly want to retire and be content, don’t live in a city like San Francisco or New York. There’s always something happening, and you’ll inevitably get pulled into the mix. It will be exciting and fun—for a while—but over time, it may start to wear on you.
Most of us won’t stop craving more until we pull ourselves out of the bakery shop. But gosh darn it those cronuts are so good!
To Your Financial Freedom,
Sam
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