Early Career
The Chesapeake economy was centered around tobacco, grown within the English mercantile system for export to markets in Britain and Europe. Randolph appears to have arrived in the province with little capital and few transatlantic connections. One historian suggests that he started off in the colony as an "undertaker" building houses, but there is no evidence for it. By 1674 he had acquired enough money to import 12 persons into the colony and thereby earned his first of many land patents (between 1674 and 1697 he imported 72 servants and 69 slaves for which he collected patents for more than 7000 acres). In later years Randolph became a merchant and a planter, and co-owned several ships used to transport tobacco to England and goods back to Virginia. He established several of his sons as merchants and ship captains.
Around 1675 he married Mary Isham (1660 Bermuda Hundred, James River, Henrico County, Virginia–25 December 1735 Turkey Island, Henrico County, Virginia), whose father, Henry Isham (c. 1628 Pytchley, Northamptonshire–c. 1676 Bermuda Hundred, James River, Henrico County, Virginia), was from a gentry family in Northamptonshire. After arriving in Virginia, Henry had married in 1659, a wealthy widow, Katherina Banks Royall (c. 1630 Canterbury, Kent–aft. 1 December 1686 Henrico County, Virginia).
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