TL;DR
- Cleo is an AI chatbot that connects to bank accounts and “roasts” your spending with sarcastic commentary
- Humor disarms shame, making users actually open the app and engage with their finances
- Warning: Never store money in fintech app wallets - support issues can trap your funds for days
- Best for: Gen Z users who avoid traditional budgeting apps due to shame/boredom
- Key lesson: Use AI for spending insights, use boring banks for storing money
Cleo’s AI chatbot uses humor instead of shame to make users confront spending habits - but one user’s cautionary tale shows why you should never store actual money in fintech apps.
Maya was $6,200 in credit card debt and felt terrible about it.
She’d tried budgeting apps before. They showed charts and graphs. She looked at them, felt bad, closed the app. Nothing changed.
Then a friend told her about Cleo.
“It’ll roast you,” the friend said. “Like, actually make fun of you.”
Maya thought that sounded awful. She downloaded it anyway.
The Sassy Financial Advisor
Cleo is an AI chatbot that connects to your bank accounts and manages your money through conversation. But unlike the sterile tone of most finance apps, Cleo has… personality.
Aggressive personality.
Maya asked: “How much did I spend on food delivery this month?”
Cleo responded: “$287 on Uber Eats. Do you even own a stove? Asking for a friend.”
She burst out laughing. Then she stopped laughing. $287 was more than her car insurance.
The Psychology of “Roast Mode”
Traditional finance apps assume shame motivates change. They show you scary numbers and expect you to feel bad enough to stop.
It doesn’t work. Shame triggers avoidance. You close the app. You don’t open it again.
Cleo took a different approach: humor disarms the shame response.
When the AI says “You spent $400 on Amazon and half of it was things you already own,” it’s technically an attack. But it’s funny. And funny doesn’t trigger the same defensive walls.
Maya found herself actually opening the app. Checking in. Asking questions.
“Cleo, how much did I spend on coffee?”
“$156. That’s approximately 78 lattes. You’re basically a shareholder at this point.”
She laughed. She also started making coffee at home.
The Gamification Layer
Beyond roasting, Cleo turns saving into a game.
Challenges: “Can you spend $50 less on dining out this week? If you do, I’ll move that $50 to savings automatically.”
Celebrations: When Maya hit a savings milestone, Cleo sent a GIF of confetti and a genuinely supportive message.
Streaks: How many days in a row have you stayed under budget?
For Gen Z users who grew up on apps designed for engagement, this felt natural. Finance became… not exactly fun, but not miserable either.
The Sober Warning
But Cleo has a darker side that Maya discovered the hard way.
Cleo offers a “wallet” feature - you can store money in the app. Maya moved $500 there for a rent payment, planning to transfer it to her landlord.
Then the transfer glitched.
She tried to move the money out. Error. She tried again. Error.
She opened the chat to ask for help. The AI chatbot responded with… circular advice. Try this. Try that. No option to speak to a human. No phone number. No escalation path.
For 72 hours, Maya’s rent money was trapped in an AI-powered limbo while a chatbot made jokes.
“I was literally about to miss rent because an AI wouldn’t give me a straight answer or connect me to a person,” she says. “That changed everything about how I see these apps.”
The Intermediary Risk
Maya’s experience reflects a broader danger: when you add a fintech layer between you and your money, you add points of failure.
Traditional bank: money in → money out. The bank is boring, but it works.
Fintech app: money in → app processes → money out. What happens when the app glitches?
Reddit forums are full of Cleo horror stories. Users with money stuck. Customer service that’s just the chatbot. Responses like “Our team is looking into this” followed by silence.
The same AI personality that makes saving fun makes emergency support infuriating. When you’re panicking about trapped funds, the last thing you want is a bot being sassy.
The Right Way to Use Cleo
After her experience, Maya didn’t delete Cleo. But she changed how she used it.
What she does now:
- Uses Cleo for tracking and insights only
- Never stores money in the Cleo wallet
- Treats it as a “fun accountability buddy,” not a financial tool for critical transactions
- Keeps serious money in a traditional bank with phone support
What Cleo is good for:
- Getting roasted into awareness (it works for some personalities)
- Quick spending check-ins via chat
- Savings challenges and gamification
- Light accountability without heavy setup
What Cleo is NOT good for:
- Storing emergency funds
- Critical transfers
- Any situation where you might need human support urgently
Alternatives With Less Risk
If Cleo’s personality appeals but the platform risk doesn’t:
ChatGPT/Claude: You can literally ask an AI to “roast my spending” after pasting anonymized transactions. Same energy, no intermediary holding your money.
Copilot Money: Has personality through visualization and smart categorization, but doesn’t hold your funds or try to be a bank.
Albert: Combines AI with actual human financial advisors you can message. When the AI fails, a person is available.
The key is separating the “fun engagement layer” from the “where your money actually lives” layer.
The Behavioral Insight
Here’s what Cleo got right, even if the execution has risks:
Most people don’t need more financial information. They need more financial engagement.
Charts don’t change behavior. Dashboards don’t create habits. But a chatbot that feels like a friend (even a mean friend) can create the emotional hook that keeps you coming back.
Maya still checks her spending. She just doesn’t use Cleo’s wallet. The AI showed her where her money went. Traditional banking keeps her money safe.
Hybrid approach. Best of both worlds.
Maya’s Final Take
“Cleo helped me see my spending in a way that didn’t make me want to crawl under a blanket and hide. The roasting was actually what I needed - it made it feel less serious, less shameful.
But the moment my actual money was involved? That’s when I learned that funny AI and reliable infrastructure are not the same thing.
Use AI to see your finances clearly. Use boring banks to hold your finances safely. Don’t confuse the two.”
