He left home in Traer, Iowa in 1872 at the age of 22 and went to work for the Northern Pacific Railroad for three years. While working for the railroad he was paid a wage of $1.50 per day for one year; then $2.00 a day and then $4.00 a day. He paid $4.50 a week for board and slept in a bunkhouse with hay as a mattress. He often went to the tramp jungle (Railroad tramps who rode the rails). At the tramp jungle, each tramp had his turn getting food for his fellow tramps, no matter where or how. Many had to beg for food but the food was shared with all. When it became James turn, he went to a restaurant and had a good breakfast of ham and eggs; then asked the waitress for the leftover garbage from the other tables to take over to the fellows at the tramp jungle. The other fellows were amazed at how he could have gotten such good food, but he never told them how he did it. The other railroad workers would blow their pay in bars while he saved and saved. He never told anyone he was saving; otherwise he would have been robbed or killed.When he finally saved $1000, he moved to Missoula, Montana and started a business selling agricultural implements, wagons, plows, all kinds of machines, etc. This he did for 15 years. In 1887 he invested in real estate, houses for rentals and lots.
At the age of 42, James met a lovely young woman, Josephine Grant Prescott. She was only 22 but they fell in love and were married. When James was asked why he hadn’t married before that he said he hadn’t met anyone he wanted to marry. until then.