Hey - it’s Jeffrey, back again!
Budgets don’t fail because you’re lazy — they fail because it’s hard to know what’s actually worth cutting.
So this week, I put that to the test. I gave my spending data to two AI tools and asked:
“If I wanted to save $300 this month, what should I cut?”
Some of their picks were obvious. Others? Not so much.
Here’s how AI helped me spot the waste — and how to run the same experiment yourself.
📬 Table of Contents:
In today’s Money Meets AI edition, we look at:
🤖 ChatGPT: Upload your budget, get real advice
🗣️ Cleo: The AI that roasts your bad spending
🔁 What to do next (Your 10-minute AI budget check-in)
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THIS WEEK’S TESTED TOOLS
🔧 Option 1: ChatGPT + Your Bank Export
Best for: a conversational option to really dig in
My goal to cut $300 in spending this week feels a little more custom, so I thought ChatGPT might be best for the job.
Here’s what I did:
Downloaded all my transactions to a CSV from the past 3 months. I chose my Citicard account.
I then asked ChatGPT: “Here are my transactions from the past 3 months. What categories or expenses should I cut to save $300? Group these by essential vs. non-essential and flag potential savings.”
Here’s the output:
ChatGPT identified some of my top spending categories, and gave me dollar amounts to reduce in each. It included savings tips too, which was pretty neat!
One challenge it faced is that ChatGPT wasn’t able to easily categorize expenses and put a bunch into an “Other” category. So I asked, “Can you examine 'Other' more to give me more details? There's a lot of spending in there.”
Sure enough, it showed me a few vendors with my highest spending and offered suggestions.
Tips for this method:
As always, blur/redact sensitive info before uploading to ChatGPT
Consider categorizing expenses before uploading them into ChatGPT, as it can’t always assign categories itself
Use 2–3 months of data
🧠 Option 2: Cleo AI app
Best for: Spending challenge suggestions to save money
Cleo is an app that connects to your bank, analyzes spending, and literally roasts you for dumb purchases.
This was my first time trying Cleo AI, and I found the funny/snarky part entertaining. Immediately upon signing up, it roasted me for my spending.
Cleo’s ‘Challenges’ feature was the most useful part for this goal. After connecting my Citicard here, Cleo analyzed my spending and suggested that I try a 14-day “Spend less on Eating Out” challenge.
It estimated I could save $104 in 14 days, and up to $312 in 6 weeks, if I stayed on track.
If I wanted to save more with another challenge, it suggested other spending categories with a quick, automated setup.
I also tried chatting with Cleo’s AI chatbot for this task. I asked it questions like “How can I cut spending by $300 each month?”
Unfortunately, I didn’t find its response relevant or helpful for this kind of question. So, if you prefer a more conversational route, ChatGPT worked better for me.
📱 Available via the iOS and Android apps
⭐ 4.6 rating (128.4K reviews) on Apple | ⭐ 4.0 rating (79.2K reviews) on Google Play
🛠️ Other Tools to Check Out
Other tools I came across but didn’t do a deep dive into for this newsletter
YNAB - my tool of choice for budgeting. It’s more hands-on and less about automation and AI, but it’s really useful for goal setting.
Copilot – Apple-only budget app with AI-powered categorization
Rocket Money - I’ve mentioned it before, and it also does a good job helping with this task.
What to Do Now
🔍 Export your spending
🧠 Try one of the tools (or both)
❌ Try eliminating one AI-flagged expense and see how it feels
THIS WEEK’S FINDS
There are tons of roundup lists out there, but this one from Making Sense of Cents stands out. It’s packed with practical, non-gimmicky ideas you can actually use.
Money stress is one of the top causes of relationship conflict. This new book tackles how to talk about money together without fighting. It's useful even if you’re not partnered up.
This NPR piece explores how AI is starting to show up in therapy and mental health. It’s a thoughtful, weirdly human look at how tech is reshaping emotional well-being.
More next week!
PS—I’d love to hear your other feedback or suggestions. Just hit reply — I read every email!
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One quick note: This newsletter is for educational purposes only and does not constitute financial advice. I’m not a financial advisor — just someone sharing ideas and tools I’ve found useful. Use what works for you, skip what doesn’t, and always do your own research before making financial decisions and using the tools shared in this newsletter.