He was the co-founder of Freeman, Shaw & Co., a cotton mill, and of Pumgustuk Water Company.

In the late 19th century, Shaw and other "dignified citizens", like Doctor James Bates and Barnabas Freeman, often assembled for an evening's chat at Englishman James Parsons' grocery store,[3] after picking up their mail at the post office next door.

[7] Shaw lived in a carriage house at the eastern corner of Yarmouth's Main and Bridge Streets.

[8] He was a co-founder of the Pumgustuk Water Company in 1887, along with Charles H. Weston, John H. Humphrey, Joseph York Hodsdon, E. Dudley Freeman and George W.

[9][10] (Pumgustuk means head of tide or falls at mouth of river.