In the rush to adopt artificial intelligence, companies are investing billions in AI tools and infrastructure. Pilot programs are launching across every department, but amid all the excitement, one crucial question often goes unanswered: Is it actually working? That’s the problem Olakai AI is tackling, and their journey from privacy-focused LLMs to AI measurement reveals a lot about navigating the most disruptive technology of our generation.

The Accidental Serial Entrepreneur

Olakai founder and CEO Xavier Casanova doesn’t like to call himself a serial entrepreneur. “I always, when I start a company, always think about my current company as my last company,” he says with a laugh. But Olakai marks his sixth venture since starting Fireclick as a Stanford student. Along the way, he’s built bootstrapped companies, led VC-backed startups, and run a publicly traded company.

Originally from Paris, Xavier came to the U.S. in 1998 and never left. “A lot of what I’ve lived through has been like between those two worlds: where I grew up and the culture and identity and who I am as a professional and now father and so on here in California.”

His path to entrepreneurship wasn’t planned—it was organic. The one time he joined a company he didn’t start, he ended up becoming CEO. “I think this just means that I am naturally perhaps attracted to be some sort of leader or carry the torch, either as my companies or the companies that I join.”

Finding the Real Problem

Like many AI companies, Olakai’s origin story involves a pivot. When large language models began gaining traction a year and a half ago, the biggest concern was data security. Healthcare companies and banks were asking: Where is our data going when employees use ChatGPT?

“Initially, our idea was to build a private LLM that could be deployed within a company’s firewall or even locally on a person’s computer and maintain privacy and security,” Xavier explains. They built a product around this concept.

But then they discovered something bigger. “Along the way, we discovered that there was a much bigger problem, which was the problem of measurement of productivity gains and measurement of the effectiveness of AI.”

The pivot came about eight months ago, and it was anything but easy. “It has a cost. It has a cost on the team, on your customers. It’s also an act of courage, I think, to be able to tell your team, look, the work we’ve done so far—we’re gonna try to reuse some of that work, but 90% is gone.”

Yet Xavier views pivots as inevitable. “I view pivots as almost like a tax of building companies. I mean, they’re kind of inevitable. I never started any of my companies thinking that I would need to pivot.”

The Always Question

So how does a company stand out in one of the most disruptive industries in history? How do you disrupt within disruption?

Xavier’s answer is deceptively simple: focus on the problems that don’t go away. “I see a lot of companies in AI that solve a particular problem today that is a new problem, but that might go away next month because of newer technology or because bigger competitors all of a sudden do your thing.”

The key is finding what he calls “the always question”—a problem that persists regardless of how fast the technology evolves. “With any new technology, you still need to measure outcomes, and you still need to put some metrics in place to kind of know what you’re doing.”

For Olakai, that question is: What’s the ROI of your AI investment?

From Pilots to Discipline

Across the enterprise landscape, AI pilot programs are proliferating. Every department wants to experiment with the latest tools. But as Xavier points out, AI is expensive. “There’s a lot of billions floating around here between Nvidia, Oracle, the energy companies, and OpenAI. And sooner or later, once we’re past this initial excitement about AI and the buildup, the questions are going to get asked.”

This is where Olakai comes in. Their platform helps companies answer critical questions at a granular level: Which AI applications are driving positive returns? Which ones need to be adjusted or stopped? And equally important—which tools are performing so well they deserve more investment?

“Finding out for a company with different functions, different AI applications, which are the ones that actually are driving positive returns and which are the ones that either need to be adjusted or even stopped,” Xavier explains. “And the opposite is also true. Some of the tools that exist today are amazing, and they’re also worth measuring.”

The need to measure effectiveness isn’t just a today or tomorrow question. “It’s an always question. And that is what gives me confidence that perhaps this will be the last pivot for Olakai, and that we’ll be on our way to be a really successful company.”

The People Behind the Pixels

For Xavier, entrepreneurship has always been about more than just building products—it’s about building teams and connections. “There’s no better feeling for an entrepreneur than having people who care about the company you’re building. Because you feel like you’re connected to these people, and you’re all working in the same direction. And that energy is fantastic.”

But he’s also refreshingly honest about the challenges. The highs are incredible, but the lows can be devastating. “When things don’t work out, sometimes it’s existential. And when you feel that, it’s awful.”

His approach to managing both? Resilience and patience. “You might be struggling with this company and the next one, and then the third one is going to be amazing. Like it would give meaning to those failures in the context of what you’re building.”

Advice for Aspiring Founders

When asked what advice he’d give to early-stage entrepreneurs, Xavier emphasizes continuous learning. “The most important thing is to always maximize your learning and always seek opportunities to meet new people, listen to them. Even if they say things that don’t make sense, be in a position where you’re always learning something from anybody.”

Why? Because entrepreneurs are fundamentally problem solvers. “You need to be exposed to real life and talk to real people to understand their problems for you to find a problem worth solving.”

His other key piece of advice: play the long game. “You have to stay curious. You have to get out, meet with a maximum number of people, stay open-minded, super resilient, and play the long game.”

But Xavier adds an important caveat about conventional wisdom. “A lot of people will tell you these things and you’re like, yeah, yeah, they’re just repeating something they heard, but it’s really true. But you only know this—you only understand the failure—after you have the success.”

The California Dream

Outside of building Olakai, Xavier finds joy in the California lifestyle he once only dreamed about growing up in Paris. He’s a private pilot who recently earned his commercial license and spends weekends flying over those “phenomenal California landscapes.”

He’s also still a soccer fan from his Paris roots, though these days he jokes that if he could be a professional athlete, he’d choose surfing. “It’s a little bit like entrepreneurial, right? It’s like you have all this preparation and you have all this energy. You want to get in the water. You want to do amazing. And it’s like hours and hours and hours of nothing. And then 10 seconds of the wave, the turn—and all of a sudden, you know that you’re going to talk about that for a week.”

It’s the perfect metaphor for the startup journey: endless preparation, relentless patience, and brief moments of exhilaration that make it all worthwhile.

Looking Forward

As Olakai continues to build out its AI measurement platform at the AI Fund, Xavier remains focused on bringing ROI discipline to an industry often characterized by hype and speculation. In an industry where companies come and go based on the latest technological shift, Olakai is betting on a fundamental truth: no matter how AI evolves, companies will always need to know if their investments are paying off.

“If you are going to choose this life, you need to be patient and ready, and things will work out in the end, hopefully,” Xavier reflects. Coming from someone who’s lived through the highs and lows of six companies, that “hopefully” feels less like uncertainty and more like hard-earned wisdom.

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Olakai is backed by AI Fund. They partner with forward-thinking organizations to set the benchmark for enterprise AI success. Learn more about their mission to ensure AI serves humanity by helping enterprises harness it with clarity, responsibility, and trust — turning innovation into measurable progress for all.