Born in Washington, PA., Dearing was named and raised by an uncle. Reared in poverty, Dearing received little formal education and left home when young to work odd jobs. At 15 he worked in the Carnegie Steel mills. By 19 he was a chef in Wilkinsburg, Penn. At age 21 Dearing had saved enough money to open a small hotel and restaurant, but saw it destroyed by a flood.
Arriving in Cleveland in the early 1930s, Dearing first worked as a short order cook until hired as manager of the popular Cedar Gardens night club at E.79th and Cedar Ave. by owner, Jack Hecht.
In 1946 Dearing opened his first (of six) restaurant at 1930 East 105th St. His second opened around 1953 at 10932 Superior Ave. and included a catering business. Dearing also opened one of Cleveland's first carry-out diners, "The Carry Out" at E.97th St. and Cedar which he sold in 1958 to open a Dearing's at 10930 Superior. In 1969 he opened a restaurant at 17234 Harvard. At the time of his death one Dearing restaurant remained, at E.110th St. and Superior Ave.
Dearing married Roberta Walker in 1936 and had two children, Ulysses Jr., and Sandra. Dearing is buried in Highland Park Cemetery.