The transformation began with a single morning realization. After years of genuinely believing he "never worked a single day" because he loved everything about his role, Matteo woke up in his Milan apartment with an unfamiliar feeling: dread about going to work. "Everything that I love about my work was about meeting talented people, meeting interesting clients, and discovering new places around the world. All of a sudden, this was kept away." This wasn't burnout from overwork; it was the sudden absence of everything that made work feel like play. The lesson: when external circumstances remove the elements that fuel your passion, you can't force the fire to return through willpower alone.

Rather than suffering in silence, Matteo made a bold choice: he told his CEO and direct manager exactly what was happening. "Look, I've lost my passion. You will still have 110% from me, but I need to find my passion or it's going to be a path of struggle." This conversation led to a mutual agreement for his exit, complete with a succession plan. The insight here is powerful for founders: acknowledging when something isn't working, even when it looks successful from the outside, creates space for authentic solutions rather than forced ones.

Matteo's departure from Frog culminated in a presentation to all studios about "10 lessons learned during my tenure." The final lesson was covered by a poster that simply read: "Love stories end." "I was nearly crying when I was delivering that last lesson," Matteo recalls. This wasn't about failure; it was about honoring a genuine relationship with work that had naturally reached its conclusion. For founders, this offers permission to end chapters of their journey with gratitude rather than forcing relationships that have run their course.

Matteo describes serendipity as "the strongest force in the universe," defining it simply as "be open for good and good will happen." This isn't passive waiting; it's active openness. While exploring various possibilities after leaving Frog, an old acquaintance called with an idea about training people on WhatsApp through micro-learning. Coincidentally, Matteo had spent that entire summer studying micro-learning for a Frontiers project. "When I see micro-learning coming from somebody I haven't spoken with for ages, I say I like it. I like it a lot." The timing wasn't coincidence; it was prepared serendipity meeting opportunity.

The contrast is striking: Matteo went from 250+ flights annually to fewer than 30, from managing teams through constant travel to building a completely distributed organization. "Nobody works in the office," he says about their Dublin headquarters. Instead of fighting remote work, he embraced it completely, offering employees unlimited budgets for home office setups. The shift revealed something crucial: much of his previous travel was based on belief ("I truly believed it was important to be in front of people") rather than necessity. Sometimes the constraints that seem limiting actually reveal more effective ways of operating.

Matteo's superpower is "being laser focused on the objective and everything that distracts me from the objective is a no for me." He describes being "ultra stubborn" once he sees an objective, noting that his co-founder Andrea is "the person I said the most nos in my entire life" because of his constant stream of new ideas. This isn't about being inflexible; it's about protecting the clarity of purpose that allows for sustained execution. The discipline of saying no preserves energy for the things that truly matter.

Matteo's story initially felt too polished. Corporate success, world travel, loving every demanding minute. But when he lost his passion, he didn't try to fake it or push through. He immediately told his leadership what was happening inside him.

Most founders suffer in silence when they hit these walls. They keep performing while everything feels hollow. Matteo honored the end of his love story with Frog instead of trying to resuscitate something that had naturally concluded.

What grabbed me was his serendipity philosophy. Not passive "everything happens for a reason" but something active: being genuinely open to unexpected opportunities. The timing of Andrea's micro-learning call wasn't magic. It was prepared curiosity meeting opportunity. Every fulfilled founder I know shares this quality.