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Also, does anyone know if a broker with Mass can do a joint work with someone that has a career contract?
Yes, you can. In fact, one reason to do this is to take advantage of the other career agent's commission advances. I believe you are paid "as earned" as a MassMutual broker, so by putting a career agent on the app to split it, entitles both to advanced commissions.
Just keep in mind that there may also be shared liability on that app as well. TANSTAAFL - There Ain't No Such Thing As A Free Lunch.