I expect we all recognize that certain relationships are of amazing value to our lives. However, I also expect we all recognize that, when things do not go smoothly in those same relationships, they can make our lives extremely difficult. Nothing is harder than knowing there is the potential of having fabulous synergy with a person, but not being able to continue to realize it. If you still think it is worth putting in the effort, here is something to take into account.
Control freaks often have trouble delegating as they expect they need to do all tasks themselves in order for them to be completed properly. Having had quite a few disappointing collaborations, I felt the same way. However, having studied certain personality theories and having experienced some great collaborations, I now truly believe that you can find the appropriate person for the concerning tasks. You need to put in some work, though.
One would say delegation is the solution to his problem. However, he is a control freak. The company is his baby. He has run it for years and relies on his own competencies.
When you are a good student you are willing to make the effort of spending time out of your comfort zone and getting in touch with the new. When you are an advanced student, you are comfortable doing this. You develop your competencies, so you can improve the quality of your actions and enjoy the fun that comes with it. However, behaving as a good student could be difficult. Is there room for improvement in your case?