Henry Failing, his father Josiah, and younger brother John arrived in Portland in 1851 from New York. The Failings opened a small mercantile store, J. Failing & Co. on SW Front (now Naito Parkway) near Oak Street. They were later joined by Josiah’s wife, Henrietta, and their three other children in 1853. The business was a rapid success, and Josiah Failing was elected in 1853 to serve as Portland’s fourth mayor. Henry Failing later became majority owner of the business, focusing on hardware and iron supplies. In 1871, Henry Failing and Henry Winslow Corbett consolidated their hardware businesses, forming Corbett, Failing & Co. This business in turn would be consolidated in 1893 with Foster & Robertson to form Corbett, Failing, and Robertson.

In 1858, Henry Failing married Emily Phelps, the sister of local businessman Henry Winslow Corbett. Through Emily’s sister Mary Freeland, the Failing family thus gained ties with the Robertson family, who owned Robertson Heavy Hardware. The grandson of Mary Freeland, Thomas Robertson (1881-1924) married Kathleen Burns in 1910, gaining ties to the prominent Couch family.