This morning, the first message I read came from a 75-year-old widow. A scam had talked her out of her retirement savings, and now she was borrowing from family just to keep the bills paid. She ended with one line: “I am typing this through tears.”
I’ve been getting messages like that since 1994. First it was phone calls, then letters, then email, then comments on a website. The messages were never the problem. I was. There’s only one of me, and I sleep.
People don’t fall apart on a schedule. They fall apart at two in the morning, at the kitchen table, with a collection letter in one hand and nobody to call.
So this year I built Ask Steve.
It’s a free AI chat on my site. When someone types in what’s going on, it starts from what I’ve actually written: more than 25,000 posts over the years, my 250 podcast episodes, my five books. It knows my voice and positions and answers the way I would in person. And behind those posts sits a research library I keep adding to, 114 books and nearly 19,000 passages, so the facts get checked against something real instead of repeated because everyone else repeats them.
I hear a lot about AI slop. Fake photos, junk articles, bots arguing with bots. That’s real. But I’ve watched something else happen.
Since late February, Ask Steve has had 1,385 conversations. Some are two messages long. Some run past twenty, somebody working through it one question at a time, at their own pace, with no salesperson on the other end waiting to close.
It’s private. I’m not selling anything. It won’t shame anybody, because shame never paid off a single debt. And when someone is in real danger, it points them to free resources and people who can help right now. Plus it gives people compassionate, actionable roadmaps they can follow themselves.
User feedback has been some of the most gratifying of my decades of helping people.
It isn’t perfect. I read the conversations, the good ones and the ones where it got something a bit off. Every miss becomes a fix. The misses are few and far between these days. That part still takes a human, and I’m glad it does, because it takes experience to know what AI has overlooked or assumed incorrectly from internet training.
What gets me is the hour. I suspect some of the people typing to it would never say these things out loud to another person. Some of the anonymous chats sound a lot like what people have shared with me in my Debt Confessional. Telling it to something patient, at midnight, with nobody watching, is how they finally start.
That’s the kind of AI I want to be part of. Not the kind that people bitch about. The kind that makes sure nobody has to sit alone with it until morning.
If you, or somebody you love, is carrying something heavy right now, Ask Steve is here, day or night. It won’t judge, and it won’t try to sell you anything.
And the Ask Steve chat, powered by AI, was only the start of how I’m using AI for good. I’ve put together a big list of free tools you can find in the footer of my site.
— Steve