[mbijon]

How do you think he would react if you hired an operations manager or director, who was responsible for tasking him with work?

This would free your time up to grow profits, help keep him productive, and also protect the friendship by having someone else evaluate him.

[superasn]

> How do you think he would react if you hired an operations manager or director, who was responsible for tasking him with work?

Actually your suggestion is good and he may react positively to that because I think he is happier when is he exactly told what to do and someone makes sure he finishes what he starts (which has been my work exactly).

But the thing about that is right now we're just two people working in an office that we've designed more as a recreation center. All our site stuff is fully outsourced and working great, so I don't know if I can find an operations manager just to babysit him.

But maybe if I can find or invent an operations manager that can work via telecommuting (why not?) just to check his progress then this suggestion maybe the best thing to happen to our business.

[mbijon]

...this isn't ideal. But with $500k/year, you can possibly consider a money-at-problem solution.

(Hiring a good ops manager is its own problem, however)