I'm researching this same line, and have found an earlier John Bolling in Henrico - he owned a lot of land, mostly for importation of lots of people, but that's the only information I can find. This John Bolling's land records go from 1702 - 1732. He doesn't seem to be related to the Pocahontas Bollings. How could someone with thousands of acres of land not leave any other traces?

Does anyone know more about this John Bolling? Could he be the father or grandfather of Ann Bolling's father?