I was sitting there with a group of CEOs discussing how to manage growth. How do you get to the next level? There are only so many hours in the day and people demand your time. This is such a fundamental issue. Many businesses hit a brick wall when they hit a particular size. They basically stop growing. This owner/founder is not able to hire a management team. He feels he's the only one who really cares about the other business. Everyone else is in it for the money, not the passion. He's tried to hire people in the past, but they just didn't work out.
The owner should look in the mirror. He is not acting as a CEO. He's afraid of ceding control. He's afraid that someone will take advantage of him and potentially lose his money. He's not willing to take the time to train his team, however qualified. It is first hard to hire a strong team. It is harder to work with them on making sure they understand their role. The hardest is letting go of decisions.
An interesting point was about deadlines. Some entrepreneurs don't typically like deadlines. They are working very hard to create something new. They can only work as hard as they can. They don't know what it's like to waste time. Many times they succeed because they are dedicated, however this is not scalable.
If you want to create a management team, you need dates. You need drivers who enjoy the motivation of deadlines. To make them stick, you need to hit them as well. You need to have incentives and consequences.
Imagine doing something one way for years, then changing by hiring sharp folks, ceding control and then changing the way you works.
This is why so few actually make it. It's hard to change, but the best know they need to mold themselves to each stage. Go from operational to strategic. Go from doer to the manager to the leader. Shift from becoming the operator to the teacher.
That's what it takes and you can do it.