Meet Your New Money Coach: She’s AI, and She Doesn’t Judge
Step one: Inherit a fortune.
Step two: Ask a chatbot what to do with it.
Step three: Almost disinherit your children.
Welcome to the brave new world of AI financial advice: smart-ish, fast, and occasionally tone-deaf. Cary Carbonaro, a Certified Financial Planner (CFP), head of Women and Wealth at Ashton Thomas Private Wealth, and author of Women and Wealth, shared the story above.
“My client had just come into an inheritance and wanted to know how to handle it. She came to me saying, ‘I asked AI what Warren Buffett does to build wealth for his family, and it told me to set up a generation-skipping trust,’” Carbonaro recalled.
The catch? The client didn’t know that kind of trust skips over her own children. “My client said, ‘Oh, I guess I don’t want that then,’” Carbonaro said. Instead, Carbonaro walked her through options that aligned better with her actual goals—protecting her inheritance, supporting her children, and still leaving a legacy for future generations.
From ChatGPT to robo-advisors, AI is muscling its way into money talk—spitting out tips on everything from retirement scenarios to grocery budgets. Yes, it’s still a shiny new toy, but one with real potential. And for women over 50—who control trillions in wealth but still get side-eyed or ignored by traditional advisors—the point isn’t replacing human advice. It’s learning how to work these tools to your advantage without getting played.
Ask the Dumb Questions—AI Doesn’t Roll Its Eyes
For midlife women—especially those newly single, semi-retired, or simply sick of being talked down to—AI can offer a starting point that doesn’t judge, interrupt, or assume your husband handles the money.
Lei Deng, CFP and founder of Savor Financial, said many of her clients—often women over 50 who are widowed or divorced—turn to ChatGPT for the questions they feel embarrassed to ask in person. They might wonder, “What’s a mutual fund? What’s an ETF?” Getting simple answers first helps them feel less intimidated and more prepared to talk through the bigger, personalized issues with her.
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Ask the Bot, Then Ask a Badass
Sure, ChatGPT can explain a mutual fund, but remember—it was written by 20-something guys in San Francisco. For women navigating divorce, caregiving, or retirement, there’s finally a chatbot designed with them in mind.
Judy Herbst, executive director of Savvy Ladies, a nonprofit that provides free financial education, championed the idea of an educational chatbot based on the success of its helpline.
The helpline, launched in March 2023, is an app that matches women with questions with professionals. The service is free, private, and backed by 265 volunteer financial badasses—CFPs, CPAs, financial therapists, and divorce specialists.
The results were immediate. “Prior to the app, we were seeing maybe three women a month. We’re now seeing 200 a month,” Herbst said. “Many are midlife women blindsided by divorce or widowhood. They ask, ‘Should I keep the house? What if I take on debt? Can I afford to retire, and will my money last?’”
A year later, Savvy Ladies rolled out an AI chatbot so women could get answers instantly. It’s fueled by vetted sources—Financial Industry Regulatory Authority (FINRA) courses and articles written by volunteers—not random internet noise. Most of what women ask is practical stuff like budgeting and debt. Demand got so high they even built a spending calculator.
Herbst put it bluntly: The bot handles quick fixes, the helpline tackles the heavy stuff. And every chat ends with a nudge to the helpline, where real experts take it from there. (Related: Polite Women Finish Last: Tough Questions I Wish I’d Asked My Financial Advisor Sooner)
The Savvy Ladies chatbot, and AI in general, is a powerful tool for learning, said Herbst. “AI democratizes the ability to get a financial education.”
What Could Go Horribly, Expensively Wrong
The enthusiasm about AI comes with caveats.
“It’s certainly not personalized. My work deals in real-life scenarios. AI really can’t,” said Carbonaro.
Chad D. Cummings, Esq., CPA and CEO of Cummings & Cummings Law, didn’t mince words: accuracy is shaky and accountability is nonexistent. “Back in July, the so-called One Big, Beautiful Bill Act passed. If you go into ChatGPT today and ask tax questions, it will still give you the wrong information,” he said. Translation: If your tax strategy is built on AI, don’t go spending that refund. And unlike human advisors, these tools carry no responsibility if their guidance goes south. As computer scientist Joseph Weizenbaum warned way back in 1976, “A computer can never be held accountable; therefore, a computer must never make a decision.”
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Your AI Money Toolkit (But With Boundaries)
You wouldn’t hand your checkbook to a stranger—so why hand your data to an algorithm? Carbonaro suggests starting slow: “Dip a toe in—don’t belly flop.”
For example, ask ChatGPT to “Explain a mutual fund like I’m 12.” You’ll get something like: “A mutual fund is a big pool of money that lots of people put together. A professional manager uses that money to buy many different investments, like stocks and bonds. When you invest, you own a small piece of all those investments instead of just one. This helps lower risk and makes investing easier for beginners.”
And if you’re using AI, please, please, don’t put in your personal information, including your Social Security number, address, email address, and account numbers. Yes, it’s in bold for a reason. Asking questions? Totally fine. But plugging in personal data for budgeting or scenario planning? That’s where you need to pump the brakes.
“Once personal data is entered, you can’t control where it goes or how it’s stored,” said Deng.
Trust Yourself. Use the Bot. Repeat.
Ultimately, Herbst sees AI as a conversation starter: “Use AI to learn all the options and choices. Then bring those questions to a real person. Don’t let AI make the choice for you.”
AI isn’t your fairy godmother—or your financial villain. It’s just a tool. Use it wisely, and it might just be your next act’s sidekick. You’re the hero of this story. The bot?
She’s just here to carry your bags.
Sidebar: Worth a Peek (Before You Hand Over Your Wallet)
These AI-powered tools promise financial clarity, but let’s be real: They won’t hug you after a divorce or stop you from impulse-buying throw pillows at 2 a.m.
Betterment/Wealthfront
Robo-advisors for when you want your 401(k) on cruise control—but without crashing into ageism.
Cost: 0.25% annual fee (~$25 per $10,000)
Mezzi
AI planner that helps you game out investing, aging, health care, and retirement—like your financially savvy alter ego in app form.
Cost: Starts at $199/year
Origin
All your accounts, goals, and anxiety in one dashboard. Think financial clarity—with fewer spreadsheets.
Cost: $1 first-year promo (yes, really)
Cleo
A budgeting app that roasts your spending and cheers on your savings. It’s financial tough love—with memes.
Cost: Free basic; Premium $6–$15/month
ChatGPT/Gemini
Plain-English explainers for the money stuff you wish someone had taught in high school. No judgment. No jargon.
Cost: Free or $20/month for fancy features
Savvy Ladies Chatbot
Financial answers from real experts, made for real women. No condescension, no paywall, no bull.
Cost: Free (thanks to this badass nonprofit)
Margie Zable Fisher is a freelance writer who specializes in topics that empower women over 50. She is also the author of The Cabernet Club, a novel about a new retiree discovering it’s never too late to become who you might have been.
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