In 1907, Frank Greenaway purchased from F. T. Wood, on a mortgage to San Jacinto State Bank, a Curtis F portable sawmill, a Curtis F shingle mill, a drag saw, a cutoff saw, a side-crank stationary steam engine, a planer, and a 45-horsepower locomotive steam boiler. The following year he renewed his mortgage with the bank.
Greenaway had apparently purchased the equipment of Shropshire & Daughtery sawmill firm, located on the Ruth Miller League sawmill near Evergreen, in 1909. Whether he ran the S & D sawmill or moved it to his complex at Shepherd is not known. He mortgaged more sawmill machinery, an engine, and a boiler to the Bank in June, 1909. In 1910, he mortgaged a Penitentiary (Star State) steam engine to the Bank.
His complex consisted, besides the sawmill facility, a cotton gin, a grist mill, and a syrup mill. Greenaway had another sawmill at Evergreen.