LAST WEEK, OPENAI founder Sam Altman sat down for an interview with venture capitalist Brad Gerstner and Microsoft CEO Satya Nadella. Both are investors in OpenAI, so it seemed like a friendly audience. But Gerstner posed a question that seemed to make Altman uncomfortable.
Since introducing ChatGPT three years ago, OpenAI has posted impressive growth, but Gerstner wondered whether the company was, nonetheless, getting ahead of itself.
“How can a company with $13 billion in revenues make $1.4 trillion of spend commitments?” Gerstner asked.

MANY PEOPLE ARE familiar with tax loss harvesting, where you sell a losing security/ETF and rebuy a similar, not identical, security/ETF.
But often we don’t really think about the opposite side of the coin: sell a winning security/ETF and rebuy the exact same, or a different, security/ETF.
That strategy is called tax gain harvesting, and because it’s a gain, the wash sale rule doesn’t apply.
 
Execution
Long-term capital gains can be taxed at 0% depending on your income.

By William Housley and my thinking partner AI (GPT-5)
A Changing Market Mood
William: It seems like the market is running on excitement. The big AI stocks are still climbing, and anyone who hesitates feels like they’re missing the boat. When everything moves that fast, can a contrarian approach really work anymore?
AI: That’s a question investors have wrestled with for centuries — what happens when momentum becomes the market itself?

Goodness. A trillion dollars—$1,000,000,000,000.00 That’s a massive potential compensation package and an awful lot of zeros. I guess if you’re already worth 400 billion, you might as well take a leap of faith and shoot for the stars. I really doubt Elon Musk will hit all the numbers to unlock the full amount. The sales and profit targets seem very ambitious, maybe even beyond Musk’s ability to achieve.
Although I personally think the possible compensation package is an obscene amount of money,

Connie and I were out to dinner recently with two other couples – longtime friends.
During the conversation one of the wives asked the other if they had received their $1200 state property taxes rebate. Yes, we got it yesterday was the reply. Connie looked at me and asked if we received it. I tried to give her a visual high-sign, but she asked again. I said no. “I guess you forgot to apply, right? I was silent and tried another “look” to signal “cool it” on the conversation.

As HD regulars know, Jonathan sought to have a meaningful legacy in the form of helping young people, especially those who otherwise might not have the opportunity, get started early with saving and investing. Thus, with the help of some of his many friends in the investing community, the Jonathan Clements Getting Going on Savings Initiative was born.
Jonathan spoke about the Initiative here and here. There’s also a thread about it on the Bogleheads forum. I wanted to make a QCD (Qualified Charitable Distribution) donation to Jonathan’s Initiative and so thought I’d outline the process I went through in the hope it might help others who are considering a QCD (or other type) donation.

The thought came into my mind the other morning when drinking coffee in the sunroom. Over the years have you ever prevaricated or had doubts about spending money on specific things, then with the gift of hindsight realised it was a great use of your hard earned cash?
The sunroom in question very nearly didn’t happen. My wife Suzie and I had closed on an old two bedroom house. We could see past the surface state and knew the plot had massive potential for refurbishment and expansion into a great home.

I’m a bit of a history buff (nerd), and lately I’ve been reading “The Roman Army: A Social and Institutional History,” a very good read if you have any interest in ancient Rome. I came across an interesting fact I was unaware of.
We have a lot to thank the 19th-century German Chancellor Otto von Bismarck for. He created the first state pension in 1889. But you might be surprised to learn that nearly two thousand years earlier,

I’m an optimist. And proudly so. Perhaps too optimistic, but that’s a risk I’m willing to take.
Having this mindset and reflecting on how I engage with money, and the world more broadly, got me thinking of two things.
Firstly, it takes a lot of work to remain an optimist in the modern media landscape. The default position of financial media is that bad news is either here or right around the corner. If the market is down,

Jonathan’s memorial service will be held at Saint Peter’s Episcopal Church, Philadelphia on Saturday November 8th beginning at 11am EST.   The event will be live streamed using Facebook.  Here is the link to the event:
https://facebook.com/events/s/jonathan-clements-memorial-ser/1159281123061275/?
My thanks to all for your condolences and best wishes. Jonathan’s reach was far and wide.  Nick.

Editor’s note: Jonathan Clements (1963–2025), HumbleDollar’s founder and a former Wall Street Journal personal-finance columnist, died on Sept. 21, 2025. This piece honors his plain-English approach to money and giving.
Jonathan Clements taught us that money is a means to a life that’s human, hopeful, and helpful. One of the best ways to live it out is to give with intention and make an impact. In that spirit—and in this season of thanks—here are 10 ways to support the charitable causes you love without writing a check.

Here in the UK, there’s an ongoing, large-scale auto loan scandal involving discretionary commission arrangements—where car dealers secretly earned higher commissions by steering customers into more expensive loans. A recent court ruling has ordered loan providers to potentially compensate millions of people who took out car finance over the last 18 years. The news has barely hit the headlines, but the vultures are already circling.
So far, I’ve had unsolicited emails from three different claims handling businesses.

Why oh why is it so hard for people to put shopping carts where they belong after use or at least not put them where they don’t belong?
Three times in the last week I have pulled into a handicap parking space only to see a cart left right in the middle of the space – a handicap space‼️   Of course, in addition, numerous carts are left in regular spaces, alongside cars and in some cases at the end of a parking lot nowhere near the store they came from. 

Jerry’s post reminded me of something I’ve been wondering about. We both hit 65 this year and started Medicare. We pay a hefty IRMAA up charge because it’s based on our 2023 income, when we were both working.
I retired in July. Though I’m drawing pension income, my gross income has obviously dropped. However, between my pensions, my husband’s pension, and his current salary, I’m guessing that filing for a change in status reconsideration wouldn’t adjust the big picture.

My sister called and asked if she should get a financial advisor.
Her question made me pause, because I’ve wondered the same thing myself.

How “right” do you have to be when you invest?
How much better does an advisor need to be to make up for their fee?
Is it more important to pick the right investments or to be tax-efficient?
And if I’ve managed to stay the course through market storms, do I even need an advisor at all?