Portland businessman, mayor, and philanthropist Josiah Failing was born in Montgomery County, New York, on July 9, 1806, to parents Henry Jacob and Mary Failing. While there is little record of his early years, Failing was noted as a motivated and engaged student during his childhood education. After being trained to paint wallpaper designs, he moved to New York City in 1824. Four years later, he married Henrietta Ellison.

During the early 1830s, Failing took a keen interest in Oregon. Although caution and family responsibility persuaded him to remain on the East Coast for the 1830s and 1840s, in the spring of 1851 he decided to relocate to Portland.

With his sons Henry and John, he opened a mercantile store on SW Front (Naito Parkway) near Oak Street. Unlike many of the other retailers who set up shop in the city, the Failings paid close attention to operating a strictly legitimate business absent of speculation.

In 1853, at forty-seven years of age, the "Dean of Front Street," as he was called, was elected Portland mayor. During Mayor Failing's one-year term, his sons assisted in the operation of the family's merchandise store. When son Henry assumed control of the business in 1854, Failing slowly withdrew from active involvement in the family's expanding business ventures.

Until the time of his death on August 14, 1877, Josiah Failing remained a prominent member of the Portland community, contributing to the Baptist Church and numerous civic and social institutions.