He was married three times and twice widowed, with eleven children of his own and an unknown number of stepchildren. His father's heirs did provide for his education, and that undoubtedly provided a foundation for a successful life. In 1803 Grubb was on the tax rolls as a married landowner in Earl Township, Lancaster County, Pennsylvania, where he was a hackle (a flax or hemp combing implement) maker and farmer, having purchased of land from Henry Schultz. The 1810 census lists him with a wife and two sons in Earl Township. His wife was probably a daughter of John Swiggart of Lancaster, and one of the sons was named Curtis, after Jehu's father. They had a third son William in Pennsylvania just before moving to Stark County in May 1811. In Ohio, Grubb first purchased a quarter section of patent land in Richland County, and another in what is now Summit County near Canal Fulton. These parcels were later sold, the first in 1815 and the second to Abraham Miller in 1833. In August 1812 Grubb was drafted as a private into the Ohio militia where he served during the War of 1812, until his discharge at Lower Sandusky on February 24, 1813. He subsequently purchased, on April 30, 1813, a third quarter section (Range 8, Twp. 11, Section 9, NE/4) in Plain Township, where he made his farm and lived out his life. In the 1850 census, his land was valued at $6,400, and in 1852 he donated a parcel to build the Whitehall School. There was also a cemetery, but the marked graves (only) were later moved for road widening. A corner of the Plain Twp. property was later acquired from Grubb's estate by his stepson and became the site of the beautiful and historic Jacob H. Bair House. Jacob was the son of Grubb's widow Elizabeth. Grubb's first wife died, most likely while giving birth to their fourth son Simon Peter on March 6, 1814. On October 8, 1815, Grubb married Elizabeth Reber, apparently a widow with children. Her parentage is unclear, as different documents give her surname as Reber and Sorrick; families with both names lived in the area. Some evidence suggests she may have been related to Frederick Reber and widowed by John Sorrick, but no connections to either family have been verified. Grubb and Elizabeth Reber had five children before she died in 1833.