Cleo CEO Barney Hussey-Yeo created a financial tool that promises to help users understand and master their money using AI. He knows that sounds intimidating, which is why he used an unusual tactic to gain users’ trust: making them laugh.

What inspired you to create Cleo?

I created Cleo because personal finance was outdated and borderline adversarial. Everything was built for institutions, not humans. I’d worked as a data scientist and kept thinking: why isn’t anyone using AI to actually help people make better decisions? The aha moment was realising a conversational AI could sit in your corner, spot patterns you can’t see, challenge your behaviour, and guide you in a way that feels natural. People don’t reason about money in spreadsheets; they reason in emotions, impulses, stress and habits. So the product had to speak that language. 

You use humor to connect with customers. What was that decision like?

Humor wasn’t branding. It was a behavioural unlock. Most people avoid checking their money because it triggers stress or shame. Traditional apps respond with charts and warnings, which only makes the avoidance stronger. A well-timed joke or moment of personality cuts through that. It lowers the stakes and makes financial feedback feel digestible. 

Related: How Streaming Is Changing the Game for Indie Movie Makers

What was the toughest problem you faced?

The hardest early problem wasn’t technical. It was emotional trust. The AI could analyse your spending and behaviour, but if the tone was even slightly off, users checked out. Money is sensitive. Get the vibe wrong once and you lose credibility. We realised we had to build a system that understood context, not just data. 

We had to learn how people actually reacted to feedback about their finances, and that required more nuance than we expected. Some people needed encouragement, others needed clarity, and others needed a direct challenge.. So we trained the AI to read patterns like volatility, stress signals, and engagement, and shift tone accordingly. Sometimes direct, sometimes empathetic, sometimes light. Once it could do that reliably, the whole experience changed. People stayed, engaged, and actually used the product to improve decisions. It taught us that accuracy alone is never enough. People need to feel understood before they are willing to change.

Related: Seven Years Ago, He Decided to Stop Doing the Expected. This Year, His Company Will Make Just Under a Billion Dollars in Revenue.

Humor also made the experience feel more personal. It kept people coming back, even on the days when their finances felt messy or overwhelming. Once we saw that people were more willing to face their money when the tone felt human, we knew it was a core part of helping behaviour stick. Combine that with Behavioral AI and you suddenly have something people actually want to interact with. The point was never to be funny. It was to keep people engaged long enough to build better habits. And it works: when the guidance feels human and personalised, people stick with it.

For other entrepreneurs building big things, what’s a productivity tip you swear by?

I treat mental focus like capital. Mornings are deep-work only: no meetings, no Slack, no notifications. I start with one question: What’s the single highest-leverage decision I can make today? I do that first. Everything else fits around it.  Context switching kills creativity and slows teams down, so I avoid it at all costs. For me, productivity is about clarity, not hours. Solve the right problem every day and the company compounds.

What’s something you wish you knew when you were starting out?

I wish I had understood sooner that your assumptions don’t matter. Real user behaviour does. You can’t think your way into the perfect AI product. You need live interactions, messy data, and feedback that contradicts your plans. The faster you get your system in front of users, the faster you learn. I also wish I had known how quickly your role shifts as the company grows. What works at ten people does not work at one hundred. The skill you need most is the ability to adapt your own behaviour, not just the product’s. Letting go of control and giving your team real ownership unlocks far more speed and clarity. Early on, you optimise for speed. Later, for clarity and alignment. And you have to let go of being right. Humility accelerates everything.

What does the word “entrepreneur” mean to you?

An entrepreneur is someone who looks at a broken system and decides to rebuild it. When I started, success meant shipping something clever that people liked. Over time, it shifted to building something that lasts.  AI amplifies what a small team can do, so you have to use that leverage well. We’re around $330M ARR, which I’m proud of because it shows the model scales. But the stat I care about most is this: the overwhelming majority of users say Cleo makes them feel more in control of their finances. That is a hard metric to move because it speaks to emotion, confidence, and behaviour rather than simple usage.