His financial advantage in life came from his grandfather whose first money was made in the food business:
In Seattle, he launched his first business, a late-night restaurant in a seedy part of town, and learned to navigate a labyrinth of saloons, opium parlours, pawn shops, loan sharks, hookers and flop houses. Later, he set up shop in Monte Cristo, a short-lived mining town just north of the city. In July 1897, when a ship steamed up to the Seattle docks with word of a massive gold strike in the distant North, Trump seized the opportunity. He opened another restaurant, catering to the thousands of stampeders who passed through Seattle, and began stockpiling supplies for his own journey. In March 1898, he boarded a ship bound for Skagway...
...With another greenhorn named Ernest Levin, he pitched a tent beside the path and opened a restaurant offering hot, simple meals to the stream of prospectors flowing past. Fresh ingredients were easy to come by: One of the menu items was horsemeat. By the end of May, Trump and Levin had made it to Bennett, where they opened the New Arctic Restaurant and Hotel. It was a two-storey building made from milled lumber, a rarity in the sea of tents and lean-tos...The Arctic was open around the clock; Trump and Levin claimed to be able to serve 3,000 meals per day. As they had in Bennett, the duo offered upscale food and discreet accommodations for men and women of loose morals. Through its first summer, fall and winter, the place thrived.