Through his father's business success in the whaling and sugar and coffee plantation industries and his mother's familial connections to the Hawaiian royal family, the Pitmans were quite prosperous and owned lands on the island of Hawaiʻi and in Honolulu.
Setelah bisnis ayahnya sukses di bidang penangkapan ikan paus, gula, dan industri perkebunan kopi, dan hubungan kekeluargaan ibunya ke keluarga kerajaan Hawai, keluarga Pitman cukup kemakmuran dan memiliki tanah di Pulau Hawaii dan Honolulu.