Deciding when to hire someone to assist you can be a sticky wicket. Sometimes you hesitate because of budget, or it could be something else altogether. There are tasks that only the entrepreneur can do; those differs from owner to owner and may be industry specific as well. I’m a broadcast consultant. My experience is what I sell to clients. There is no one on my team with my radio station ownership experience, etc., so I choose to hire people to do the other stuff. Some sellers, for instance, have honed the skills of product sourcing: knowing, either by instinct or from experience, what to buy and for how much. With few exceptions, they usually are on the mark. Product sourcing may not be the thing to outsource if you have that “sourcing gene”. Instead, you may want to outsource your listing duties, for example. IF you’re thinking about hiring an assistant, take stock of your own skills first.