Antifragile Companies and Authentic Leadership at OSA36

Participating in the 6th edition of OSA360 was an intense and truly special moment. Standing before a community of entrepreneurs who, over six editions, has brought together more than 13,000 people, I felt both the joy and the responsibility of sharing my journey and some reflections on how to lead companies in a world changing at unprecedented speed.

On stage, I talked about how, back in 2002 during my studies in England, I realized that traditional hierarchical structures—so common in many Italian companies—often hinder collaboration and shared responsibility. In a slower era, they may have been efficient; today, in the face of global crises, wars, epidemics, and continuous technological transformation, they have become fragile. Companies now need to be antifragile: not only capable of resisting shocks, but able to grow stronger because of them.

Throughout my journey as CEO, I also experienced the opposite extreme: removing all rules and organizational charts does not automatically generate innovation. Too much freedom can create paralysis. I learned that real autonomy is born from clarity—from shared rules that enable people to act confidently, just like the boundaries of a playing field.

With the support of experienced consultants, we introduced new organizational models inspired by the social technology of Holacracy, shifting operational power to people, defining clear roles, and fostering transparency and distributed responsibility. I shared a principle that guides our work every day: responsibility cannot be delegated—it must be enabled. And taking care of people means creating the conditions for them to express themselves freely, not “managing” them.

I invited the community to embrace the courage to let go of traditional power in order to gain a new one—more distributed and far more effective—to pursue organizational clarity, trust, and transparency. And above all, to integrate human and artificial intelligence with courage: to experiment, to make mistakes, to learn, without stopping at immediate ROI.

Weeks have passed, yet the energy of the OSA360 stage is still vivid. It was a pleasure to talk about how to build antifragile companies—a topic that is deeply meaningful to me.

What does “antifragility” truly mean in business? How do we explain it? How do we bring it to life?

We’re living in an age where crises, wars, and technological revolutions move faster than our ability to adapt. Companies can no longer limit themselves to resisting. They must learn to grow through difficulties, to transform shocks into evolution. Being antifragile means trusting people, distributing power, creating clarity, cultivating freedom within shared rules. It means not controlling—but enabling.

The future belongs to those who integrate human and artificial intelligence to build organizations capable of improving every time the world changes.

And today, looking out at that audience, I realized that this future has already begun.

It was a powerful, emotional moment. Seeing the audience rise to their feet at the end of my talk—my first standing ovation—was a strong signal: there is a real desire for change, for a new way of doing business.

A special thank you to Mirco Gasparotto for giving me the opportunity to bring these themes to the OSA360 stage.
Let’s invest in our future and in the future of our country: let’s make mistakes, learn, evolve. Always.