There is a specific kind of dread that comes from opening a banking app you have been avoiding. I know it well. For most of last year, my entire financial strategy was hoping.
I am not bad with money in a dramatic way. There was no gambling, no shopping addiction. My problem was quieter and, I suspect, far more common: I simply did not look. Every payday the balance went up, and by the time the next one arrived it had somehow gone flat again, and I could never have told you where. So in the spring I ran an experiment. For 90 days I would let AI watch my money instead of me. Here is the honest debrief.
Week one: the app that roasts you
I started with Cleo because a friend would not stop talking about it. Cleo is a chat-first budgeting app instead of spreadsheets and category wheels, you literally text it like a person, and it texts back. It connects to your accounts through Plaid on a read-only basis, which matters: it can see your transactions but it cannot move a cent.
The gimmick is the personality. There is a “roast” mode where the AI calls you out for your spending, and a “hype” mode where it cheers you on. It sounds silly. It is a little silly. But something about being told, in plain and slightly mean language, that I had spent an absurd amount on food delivery in a single week did what a pie chart never had: it made me feel it. Within days I had cancelled two subscriptions I had forgotten existed, which Cleo flagged automatically.
Cleo's limits showed up fast, though. It is brilliant at awareness and genuinely weak at structure. I could feel the shape of my spending, but I still could not see my whole financial picture savings, investments, the slow creep of my net worth. For that, I needed to graduate to something more serious.
The switch: from vibes to a real dashboard
So at week four I moved to Monarch Money, the app a lot of people landed on after Mint shut down. This is a different universe. Monarch pulls every account checking, credit cards, investments, even my mortgage into one clean dashboard.
Its AI layer is understated but useful: there is an AI Assistant you can ask plain-English questions like “how much did I spend on dining out last quarter?” and it answers from your real data, plus a weekly recap that summarises where the money went while I wasn't paying attention. Monarch is transparent that it uses a mix of models from providers like OpenAI, Anthropic and Google, and says it does not sell your data or use it to train outside models.
The difference in how I behaved was the surprising part. Cleo changed my daily choices. Monarch changed my monthly ones. Seeing net worth as a single number and watching it move turned money from a source of dread into something closer to a game with a score.
What actually changed after 90 days?
Three things, concretely. First, I found roughly $60 a month in subscriptions and forgotten recurring charges and killed them. Second, I set up an automatic transfer to savings the day after payday, before I could “feel rich” and spend it. Third, and this is the one I did not expect, I stopped feeling anxious about money not because I suddenly had more, but because I finally knew where it was.
Here is the honest caveat, though, and no glossy app review will tell you this plainly: these tools are mirrors, not hands. Monarch is a reporting tool. It shows you the truth beautifully, but it will not stop you spending. If your core problem is impulse rather than blindness, a dashboard alone won't save you. The AI gives you clarity. What you do with the clarity is still entirely on you.
So which one should you actually use?
If you have avoided your finances for years and need a way in that does not feel like homework, start with the free tier of a conversational app like Cleo. If you already know your problem is visibility across multiple accounts, go straight to a full dashboard.
If you want the longer comparison the tools I tested that didn't make this article, the exact features, and the current pricing, I leaned heavily on this breakdown of AI tools for expense tracking and saving money while I was choosing, and it is the resource I would hand my past self.
Ninety days in, I still open a banking app most mornings. The dread is gone. That, more than any dollar figure, is what the AI actually changed.
This article reflects my own experience over roughly three months. It is not financial advice. App pricing and features were accurate at the time of writing but change frequently verify current terms before signing up. Some links may be affiliate links; they never change which tools I recommend.
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