Nicole Weiss

The digital twin enters the boardroom Kevin O'Leary has transitioned from traditional media to a high-tech future by indexing 12 terabytes of his personal history. Using Artificial Intelligence, O'Leary can now retrieve specific frames from decades of footage within seconds, a feat once impossible for human memory. Beyond simple indexing, he has developed a digital agent—an AI clone trained on his specific voice intonations through continuous recording. This agent is designed to manage the heavy lifting of his professional life, signaling a shift where personal brands are no longer limited by the 24-hour day. Implementation versus true innovation While O'Leary utilizes AI for execution and data management, he maintains a sharp distinction between implementation and pure innovation. He argues that AI remains formulaic, producing "slop" when asked to create original essays or music. To O'Leary, the human element thrives on randomness. He recounts a spontaneous collaboration with Nicole Weiss at LVMH to design a diamond necklace based on a Kobe Bryant trading card. This type of non-linear thinking—connecting disparate luxury markets on a whim during a morning bike ride—is something he believes machines cannot replicate. The value of the beautiful mistake In a world obsessed with algorithmic perfection, O'Leary finds value in human error. He cites Miles Davis and the recording of Kind of Blue as the ultimate example. The original release was recorded on a faulty machine, making it slightly slow and technically "wrong," yet it became a masterpiece. AI, by its nature, lacks the soul found in these nuances and distortions. For the high-level professional, the lesson is clear: use technology to manage your data and scale your presence, but never outsource the unpredictable spark that creates true value.