I have spent much of my working life among entrepreneurs and business leaders wrestling with a deceptively simple question: when is it time to let go? Twenty-seven years ago, I founded TIGER 21, the premier global peer network of some of the world’s most successful entrepreneurs and executives. I remain its non-executive Chairman, though 18 months ago I ceded control to a new owner, and now spend more of my time managing my own family office.
Over those years, I have watched extraordinary founders build remarkable organizations, and I have also watched some stay too long. Few decisions reveal more about a leader’s judgement than knowing when their continued presence strengthens an institution, and when it begins to weaken it. That same pattern appears far beyond business.
