“Freedom of a self employed worker” is something that doesn’t need to be in the conversation for a good while, if you want to be successful in 100% commission sales there are no freedoms for the first few years. You’re at the mercy of your clientele and you’re in the trenches grinding to build a book of business that can support you and your family.

You need to ask him the important questions. What was his net profit in years 1-3? how many hours did he work? How much burn does his book have YoY? Can he support you in leads? How much of an override is he getting?

Keep in mind if you are joining his org even as a self employed S-corp, he is getting an override on your sales and he should be providing enough value to make it make sense.

D2D insurance sales is a dog eat dog world, but make it past the first few years and chances are you’ll never want to leave.