Records from the United States Freedmen's Bureau show that it paid John K. Gewinner $12 on September 1, 1866, for allocating two rooms in his home as a Teacher's Home. Konrad died in August, 1869. The 1870 census lists Barbara as a hotel keeper. Also listed in the Gewinner household in 1870 was Col. Garrett Nagle, 33, the Williamsburg County Agent for the Freedmen's Bureau at that time. According to Edwin Christopher Epps' unpublished reminiscences of growing up in Kingstree, Mrs. Gewinner also ran a small shop located on Main Street across from the courthouse during the late 1870s and 1880s. He does not specify what she sold in her shop, but she was one of the few women business owners of that period.
The Gewinners' daughter, Mary Frederika, was appointed postmistress for Kingstree in 1866, when she was only 18 years old. The Charleston Daily News of July 27, 1866, noted, "The Kingstree Star of the 25th boasts of that village now having a regular "reconstructed" post office, Miss Mary Gewinner having received the appointment of Postmistress. The Star says that Miss G has been attending the mails for some months past. Miss G, it would then appear, has been more successful in her attendance on the mails than many of her sisters."
Mary Gewinner married Louis Jacobs in 1870 and over the next 10 years, the couple produced eight children. In 1880, they moved to Charleston, primarily because Mr. Jacobs felt it was cheaper to move his family there than it was to arrange lodging for his children to attend school in Charleston. Barbara Gewinner died in 1893, and when the Jacobs family returned to Kingstree, Louis Jacobs built a Charleston-style home on the old Gewinner lot at the corner of Main and Longstreet. The interesting feature of the home was that its back faced Longstreet, with the front of the house facing the interior of the lot.
In the late 1890s, one or more of the Jacobs' daughters went into the millinery business with one or more of the Benjamin sisters. Benjamin & Jacobs Millinery operated out of a store Louis Jacobs owned on the west side of Academy Street, where the Downtown Café is today.
On April 1, 1898, Louis Jacobs, following in his wife's footsteps, was appointed postmaster for Kingstree. He immediately moved the post office from the east side of Academy to the building on the west side that had housed Benjamin & Jacobs Millinery. The County Record, in announcing the move, also noted that Louis Jacobs' daughter, Etta, would serve as Assistant Postmaster.
Etta Jacobs, however, was already certified as a teacher and had taught in the Sampit section of Georgetown County in 1897. She later taught at Smith's Mills in northern Williamsburg County, Gourdin, and Heinemann, and in 1907 was named the principal of Salters High School. She later taught near Spartanburg, before returning to Williamsburg County as an assistant teacher in the school at Cedar Swamp. During her years in education, she was extremely active in Williamsburg County Teachers' Association, where she served on the executive committee for a number of years. She was also a member of the School Improvement Association of South Carolina. She was also a sponsor of Camp James McCutchen, an organization of Civil War veterans.
After her father's death in 1913, she left teaching to run his insurance agency, re-naming it the Etta Jacobs Agency. The Town of Kingstree treasurer's report shows that from 1914 through at least 1917, the town was paying insurance premiums to her agency. Ad ad in the November 29, 1917, issue of The County Record, signed by the Etta Jacobs Agency and Kingstree Insurance, Real Estate, and Loan, warned businesses carrying fireworks that they must first secure a permit from their insurance company to do so. If they did not get this permit, their policies would be canceled immediately.
While Etta pursued a career in education, her older sister, Mary, known as Mamie, took over as assistant postmaster. She served in this capacity for 15 years until her marriage to Theodore B. Gourdin, the great-uncle of Governor Henry McMaster, and a subsequent move to Salters. Mamie was also a loyal member of the Kingstree Civic League, serving as its secretary.
The youngest of the Jacobs' daughters, Florence, known as Florrie, made her mark as a legal stenographer. She began her career at the Kingstree firm of Lee & Shuler, but spent the last 10 years of her life employed by attorney Samuel Want in Darlington. She was rated as one of the most expert stenographers in the state of South Carolina.
Two of Louis and Mary Jacobs' daughters-in-law also exhibited an entrepreneurial spirit. In the spring of 1929, Freda and Edith Jacobs, wives of W. N. "Nappie" and Cecil Jacobs opened the Cottage Tea Room at the home of Edith and Cecil Jacobs. This house was located across Longstreet from the Jacobs' family home. The announcement of the tea room's opening in the April 11, 1929, issue of The State, noted that "this is an ideal location as the Atlantic Coastal highway with its daily rush of tourists passes directly in front of Mrs. Jacobs' home. The tea room, which remained in business for several years, was also the site of many local luncheons, showers, bridge club meetings and birthday parties. In December, 1930, Edith and Cecil Jacobs hosted a Christmas dinner at the tea room for the managers and assistants of Kingstree's filling stations.