Pros
All of the tutors plus the supervisors are friendly and supportive. Joel, without micromanaging, built an awesome company and spread it through word of mouth. All the parents and students are kept totally in the loop regarding their progress - an open and transparent customer experience. These relationships are really important and there's so much to be gained for both parties when a student with great potential gets a quality tutor and program. Flexible work hours, good snacks in the office, and a lot of students who I'd call good friends at this point.
Cons
Getting to know coworkers is inherently tougher in a gig like this because most time on the clock is spent with the student or in the car. Travel time/itineraries could be somewhat oppressive and limit work hours/necessitate big weekend days. Some inevitable difficult student/parent situations (though far fewer than I expected)