The Pupkewitz family business was founded by Harold's father Max in 1902 as an ox wagon building and repair enterprise. In 1904 at the onset of the Herero and Namaqua War he opened shop in Okahandja, strategically situated between Windhoek and the coastal towns of Walvis Bay and Swakopmund. Max Pupkewitz travelled to Europe in 1912, was jailed for his support of the German colonialists, and only returned in 1920. At that time, railways had been constructed and the era of ox wagon transportation in South West Africa was over. Max Pupkewitz opened a general dealer business in Windhoek in 1925, the year the rest of the family resettled here.