Wolstenholme depended heavily on his father, Sir John, for the shape of his early career. He was admitted to Gray’s Inn alongside him in 1611, rather than waiting until after he had attended university, and his membership of the Virginia, North-West Passage and East India Companies reflected the fact that his father was a prominent figure in each organization. In 1619 Sir John obtained a revised grant of his existing collectorships of impositions and Tunnage and Poundage so that his son could share this office with him. Four years later Wolstenholme became collector of pretermitted customs in the port of London, another position previously held by his father. At around the same time the king awarded Sir John and another customs farmer the benefit of a £10,000 bond, and Wolstenholme received his father’s share.
Although the precise means by which Wolstenholme obtained a parliamentary seat at West Looe in 1625 and 1626 have not been established, his father almost certainly had a hand in this too. As a Navy commissioner Sir John had regular dealings with (Sir) James Bagg II, the vice-admiral of south Cornwall, and it seems likely that Bagg, who had himself represented West Looe in 1624, used his influence with Sir Bernard Grenville†, one of the borough’s patrons, to secure Wolstenholme’s nomination there.
Sir John’s purchase of Nostell Priory in 1629 provided Wolstenholme with a base in Yorkshire, and during the following decade he was drawn into local government there.
