His paternal grandfather, Abner Matthews was a native of New Hampshire, settled in Burford before 1801 and was ordained as a Methodist Episcopal minister in 1820.

[1][3] In the early 1880s his reputation in the grain trade was substantial enough that he was made president of the Toronto Corn Exchange Association, which he represented in 1883 before a parliamentary standing committee on the bill to form a court of railway commissioners in Canada.

In addition, by 1898 Matthews was a director of the Empire Produce Company and chairman of the government's eastern board for grain standards.

[1][6] Matthews, in partnership with Edmund Boyd Osler, owned a sizeable share of the Hamilton Steel and Iron Company Limited and worked with him at Dominion Bank.

[1][5] In 1913, Henry Robert Emmerson said that Matthews, based on his presence in 18 companies, was one of the 23 "capitalist-directors" who "are the directive forces in practically all of Canada's economic life."

In 1909 Nathaniel Samuel Fineberg had stated in Moody's Magazine, from the sheer number of Matthews's directorships (17), that he was the second most influential business figure in Canada.