He spent quite a bit of his childhood in Milton, Massachusetts and came west in 1866, for certain years representing the apparel firm of Philip Wadsworth and Company, of Boston.

[1][2] Several years later, with his uncle, William H. Rand and Andrew McNally, he formed an association which acquired the job printing plant of the Chicago Tribune.

This organization was later consolidated under the name of Rand McNally and Company, of which concern he was treasurer until 1879, when with his brother, William H. Poole, he established the printing house of Poole Bros. For a long time the work of the firm was limited to printing for transportation organizations, with a support that included for all intents and purposes nearly every railroad in the nation.

The concern had the refinement of being the largest one in the United States solely occupied with transportation printing, yet in later years the business was extended until it appreciated an enormous commercial support too.

He was a Mason and a member of the Union League, Flossmoor Country, Windsor Golf, and Biscayne Bay Yacht, clubs.