He was appointed to the position of secretary in 1615 and sent to the colony to sit on the council of then governor Thomas Dale. Here he found an ally in marshal Thomas Redwick, with whom he managed to acquire significant and wealth in the management of the colony, often bypassing Dale thanks to his personal influence in the Virginia Company. Farlow managed to enrich himself during the governance of Samuel Argall by controlling both the import and export to and from the colony and putting in place a highly effective tariff system, enforced with the assistance of marshal Redwick.
The 1619 arrival of the new governor, George Yeardley, weakened the position he build for himself as Yeardley proved less willing to share in the profits of corruption. This caused Farlow to work more closely with plantation owner Edgar Massinger in order to undermine the position of the governor.