Newsletter for Nov 30, 2025: Thanksgiving, Travel Guilt, AI Growth

I hope everyone had a wonderful Thanksgiving! Our family of four enjoyed a satisfying turkey meal at home, followed by some tennis and biking with the kiddos.

Most of us spend Thanksgiving appreciating the friends and family still in our lives, and I’m no different. It’s funny, no matter how much wealth you accumulate, it still can’t beat the warmth you feel when someone you love appreciates and supports you. At least, not for me. Money fills your pockets; people fill your life.

Going back to your childhood home is always a time warp. Everything feels frozen in time. It is a reminder of how far you’ve come, what actually matters in the end, and how ephemeral everything really is.

This year, I’m thankful that I can still think, create, and compete (new post). One day, my mind will slow and the synapses won’t fire like they used to. But not yet.

Besides friends and family, what are you thankful for this year?

Evidence of a K-Shaped Economy

In my post, Survived Basic Economy, Then Won The Lottery, I included a short video of my return flight. The plane was about 90% empty. Naturally, like a boss, I claimed the middle seat and spread out without a neighbor on either side.

But you know what was full? First Class. All 16 seats. Meanwhile, Economy looked like a movie theater the week after a blockbuster bombs.

It made me wonder: is this the K-shaped economy in action? The top keeps spending and pulling ahead while the rest tread water or sink. Maybe the economy isn’t as strong as the headlines say. Maybe the layoffs are finally hitting consumer spending. Or maybe… not many people want to visit San Francisco and the mainland from Hawaii the week before Thanksgiving.

Either way, as investors, it’s something to think about as we head into 2026.

Too Funny Feedback

One of my favorite parts of writing is hearing from all of you. And reader Bill sent in this comment that made me laugh:

The last time I flew economy, I had an aisle seat with a husband and wife sitting next to me. The wife was extremely sick, throwing up constantly. At first she tried lying on her husband’s lap, and eventually she lay on the floor, stretched across all our feet. The flight attendant tried unsuccessfully to get her back in her seat. The husband was extremely apologetic, and I felt horrible for his wife. However, after that flight I promised myself I’d never fly economy again.

Forget suffering! I suffered during my working years so I would eventually have the means not to suffer during my later years. Isn’t that what all the savings and sacrifices were for? Next time you fly economy, check out the faces in first class. If you see a 50-something guy smiling profusely, that’s me.

Bill gets it. Suffering is for the accumulation phase, not the decumulation phase.

Saving Your Marriage

Given my recent travels, I thought it’d be useful to write something for the stay-at-home spouses who feel annoyed, or outright pissed, at their partner’s travel schedule.

As a stay-at-home dad, most of my interactions are with stay-at-home moms during playdates and school events. And one mom, in particular, was fed up. Her husband was traveling for yet another trip she believed could’ve been a Zoom call. We all survived COVID without traveling, so what’s with the huge shift?

Long-term imbalance leads to resentment, which leads to… well, the division of assets. So I wrote something I hope helps both sides see a workable solution.

Check out: How To Overcome Travel Guilt As A Stay At Home Parent. And if the article saves your marriage, do let me know so I can send you my mailing address for a nice bottle of wine. Curiously, when a neutral third party suggests something, both sides magically become more reasonable.

Another Sign You’re Working Too Hard

Folks, I have to admit: I’m burning out this year. I’ll share more in my year-end review. But maybe it’s why I’ve been writing more articles encouraging everyone, including myself, to relax and work less.

During my trip to Hawaii, my 70-year-old recently retired uncle mentioned a new way to log into Social Security through Login.gov. For 12 years, I’d tried and failed to access my benefits. Then, suddenly, with this new system, I finally got in.

And what I found was a treasure trove of information that made me realize many FS readers are massively over-optimizing. After reading my post, you might be $1 million closer to your retirement goal, or can shave off 1–5 years of unnecessary work.

Check out: Living Solely Off Your Social Security Benefits Is Possible

Latest AI News

Finally, although public AI stocks corrected a couple of weeks ago (and then rebounded last week), Anthropic went on to raise another $5 billion from Microsoft and $10 billion from Nvidia at a staggering $350 billion valuation. That’s up from $185 billion in September 2025. Unreal!

We’re talking about regular Anthropic employees with $200,000 stock packages now sitting on roughly $5 million two years later. And since almost none of us can get jobs at these companies, the only realistic way to participate is by investing in them.

Thankfully, Fundrise Venture owns some Anthropic, although I wish it owned even more given the company’s explosive growth. I also suspect Databricks, Fundrise’s largest AI holding (~20% weighting), will announce a new positive round of funding within the next 12 months, though no guarantees.

On the flip side, Figma (FIG) is now down about 70% from its first-day IPO close of $122 per share. Its current market cap sits around $17.8 billion, which is now $2.2 billion lower than what Adobe offered to buy the company for back in September 2022.

My two takeaways: be careful chasing IPO hype, and consider allocating more capital to private growth companies. Since private firms are staying private much longer, a greater share of the gains is now accruing to private investors.

To Your Financial Freedom,

Sam

Fundrise has been a long-time sponsor of Financial Samurai, and I’ve got about $800,000 invested with them across several accounts and products. My goal is to diversify, generate more 100% passive returns, and hedge against a future where AI leaves my kids unemployed after 17 years of education.

If AI really is revolutionary and my ~$500,000 venture position compounds at 15% a year for 15 years, each kid will have a secret ~$2 million security blanket to help them launch, if needed. And if they don’t need it, I might finally upgrade to Economy Plus, baby!

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