Not enough thought goes into safely transitioning from scrappy startup to mature enterprise. Attitudes, culture, and practices have to change. It gets super awkward, and it's a rare CEO that does both well.

Practically speaking, I spend a lot of time paying down technical debt incurred during the startup years, and practices are only just maturing to where we're not digging ourselves a deeper hole anymore.

It's a fascinating period to learn to navigate.

It is very rare for a startup leader (usually very hands-on and practical minded) to be able to delegate and think strategically well enough to survive the transition.

Sometimes they even lack breadth in their experience (because, well, their experience was the company's startup phase).

What to do, then? replace them with outsiders? That would not be fair, and it destroys company culture. Leave them be, knowing that they're not up to the task? That's even worse, the people under them will suffer.

It sucks that the most common answer is that eventually there's a crisis, heads roll, corporate suits take over. Thus starts the period where the graph goes up and the product goes down.