Spot on, and it's really really hard. I had the privilege of working for a CEO who scaled his business from < 20 people when I joined to ~300 when I left. You really feel each of these stages and it's very difficult to ride the transitions through them, especially if you've done a good job in phase one and you have strong product fit with your market, the business kinda just gets sucked along for a while and it's hard to "feel" the break points if you will. There is a transition from the tactical CEO to the thoughtful CEO that is hard to describe and seems hard for many of the CEOs I coach to execute. Not transitioning quickly enough through these stages and steps, and remembering to somewhat modulate your message regarding the vision mission and purpose stuff results in very uncomfortable periods of time, especially uncomfortable if your company has caught up to your thought. I do think CEO at scale is an incredibly difficult job.
Someone simplified this to the CEO's job at less than 20 people is to say "Yes" with more than 20 people say "No". His idea was at the start you need to make sure that everything get's done and everyone get's paid. AKA, from backups to taxes there are a lot of critical check-boxes to getting off the ground and you need to get all that done while building something that people want AND selling it to them. The worlds on fire and there are far to many critical things that need to be done right now.
But, somewhere around 20 people you should have some excess time and money and choosing what not to do becomes just as important as what to do. Let's not do this manually, let's not build this in house, let's not piss off our customers, let's not stagnate, etc. At scale the minefield grows exponentially and it's not getting stuff done that's the core problem it's getting the right things done while not wasting resources.
Remember hiring people is easy, having them be a net gain is the hard part.
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.
