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Rob,
In response to your first question, I think it will be different for everybody. Without knowing his financial needs, it is really hard to say. I can tell you for me, I planned for a year, worked part time for a year and then was pushed to make the change. What I did to prepare was I started advertising significantly before I made the jump. I handled the work load be using subs, and working a ton. I kept packing some monies away so I had enough for 3 months expenses. That for me made the transition easy. Some people are going to have a harder time then others leaving the safety net of an employer. It sounds like he has a good base to work on, so it does not sound like it would take him long to make a full schedule.
#2 I say definitely treat at the same time. There is nothing I hate more then going to one of my mowing clients and see that the chem guy came, and he was not on schedule. It just makes things much nicer when you can schedule your apps after you mow the property for the week.
#3 I think this guy should definitely keep the mowing and the apps. Reason being when you first start out you are looking for all the work you can, and there is nothing like mowing contracts for up-selling clients on other services. Depending on the type of mowing he is doing I know the margins are not the best, but what he can recoup from other services will be worth it at this stage. After a couple of years he can be a little more selective on the services he would like to carry.
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Matt
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