In a thought-provoking interview last October, Airbnb's founder and CEO, Brian Chesky, opened up about the intricate challenge of succession planning at tech giants like Apple. Speaking with Nilay Patel, he addressed a fundamental issue that few dare to tackle: the struggle to find a capable successor to Tim Cook.

"Succession planning is tough, especially because the standout product visionaries are often younger and, admittedly, less experienced," Chesky stated. He highlighted the reluctance to appoint younger leaders in large corporations. Employees often hesitate to accept guidance from someone who may be extraordinarily talented yet lacks the maturity typically expected in a CEO.

Chesky pointedly noted that founders can lead teams that are older than them with relative ease due to their foundational status. However, non-founders face an uphill battle when managing teams comprising older, more seasoned professionals, even if they show remarkable potential.

He drew comparisons to Microsoft CEO Satya Nadella, suggesting that while Nadella's technical background revitalized the company, it largely brought Microsoft back to the strategies established by Bill Gates. According to Chesky, what Apple truly needs is a leader who embodies the spirit of product innovation—someone akin to a chief product officer—who can streamline operations and enhance the company’s vision.

Chesky's insights offer a refreshing perspective on what many term "Founder Mode." He insists that the enchantment surrounding founders is more about the vibrancy of youth than any magical qualities they possess. To truly lead a massive corporation with youthful vigor, the leader often needs to be a founder.

Reflecting on the past, he referenced the return of Steve Jobs to Apple at the age of 42 after a lengthy absence. This return fueled the idea that understanding Apple’s core philosophy is best grasped by those who were with Jobs during his influential years.

Yet, contrasting this, he pointed to Sundar Pichai, who became CEO of Google at just 43, successfully navigating a different corporate landscape that embraces youthful leadership.

As Apple gears up for a critical transition, Chesky's remarks underscore the unique challenges and opportunities that await its next CEO. Will Apple find a founder-or even a well acquainted visionary to carry the torch? The tech world eagerly awaits.