09/03/2026
A friend told me at the gym last fall that he had been talking with ChatGPT about investing.
He said it the way people confess they cheated on a test with notes written on their hand. Lowered voice, quick glance around, the whole production. He was finally making real money with some excess to invest, he wanted to do it correctly, and I had been running investing classes for women at the time so he was not in the room for those. He went and found his own room. Then he felt bad about it.
He had nothing to apologize for.
He was not embarrassed about the money. He was embarrassed about not already knowing, which is the same sentence I hear from women running businesses at half a million a year. Different rooms, identical sentence. I should know this by now.
Nobody knows this by default. There is no class. Most of us got handed a form at 22, told to pick a percentage, and everything after that came from a podcast or a friend or a book written for somebody in a completely different situation.
So a tool that will explain any of it, at any hour, with no judgment in its voice, is a real thing to have. I use it constantly. I ask it to explain concepts to me like I am a sixth grader and it does, and I walk into decisions steadier than I did before.
It also has a hard limit, and the limit is not where most people assume it is.
I wrote the whole thing out this week, including the three questions I would never put to a chatbot and the ones I ask constantly.
Link in comments.