Coincidentally, I think the 300 number is another transition point. Until 300, you can be a CEO who really holds the wheel on many aspects of the company. Beyond this, you really have to be comfortable with delegating to your lieutenants, and empower rather than control.

The CEO at my previous employer successfully took 3 companies to exit, each at around the 300 mark. Terrific starter and operator capable of making really tough calls (like saying no to ominous AAPL supplier terms despite the obvious upsides), but quite bad at delegating.

Still wondering many years later if there are any predictors for someone who can make this transition.