I think he means,''side jobs,'' beside his full time tree job(Lets hope) At the risk of being called some mean names, I think most employees of tree Companys have done some side jobs to put a few dollars in their pockets. I have done it my self many times(hack?) This is where most guys learn what underbidding is and how important the right equipment is. I'v seen many a climber get in over their head on what they thought was a easy job.
Doing any kind of job with out insurance is asking for trouble, and its the homeowner who gets screwed if something goes amiss. To get insurance you need a business lic. and probably a contractors lic. depending on your state.
I see lots of guys get jobs while on the job, that is the same as stealing, same goes for "borrowing" Company equipment with out asking, even for the weekend.
Setting up a legit business with insurance is your right as an American. Doing jobs on the weekend is how some have got their start. But shoot for legit, protect your reputation, Don't steal jobs from your company and try to justify it like I see so many do. And make sure your qualified to do proper work. Most utility tree guys suck at doing good pruning.