I’ve tried propagating jade in the past and have never gotten it to work. Since I have a bunch of smaller pots now I thought I’d try again. But this time I did some research on how to do it. Apparently in the past when I was just sticking the leaves into soil I was doing it wrong.
I’ve read that you should let the leaves sit on top of the soil and they’ll take root. I also have a stem that I’m trying to root. With any kind of luck I’ll have some new plants started in a few weeks. And if I have no luck at all I’ll have five small pots looking to be filled!
Perched Ponderings 
You can also try sticking the stems in water until they sprout roots and then move them to a loose soil. Or in a rooting mix (it is usually sort of gravely). And I think my grandmother used to pin them to her curtains and mist them with a spray bottle every day until they sprouted roots. LOL (She had a gigantic jade plant in her apartment.)
Thanks for the tip! So far the cuttings I have seem to be doing okay (at least they’re not dead yet!). If this method doesn’t work I’ll try one of your grandmother’s. Our plants are big enough that I can take more leaves from them without a problem.