Before Dom Montgomery was paid to play hockey professionally in the SMJHL and SHL, he got most of his cash from odd summer and fall jobs in Michigan. The summer he turned 13, he got paid to deliver food in his inflatable dinghy to sailors outside of the harbor his parents had their boat in, sometimes getting some of their food as well. He also got paid a little to help clean up boats, though he did a worse job at this, so that request didn't come around as often. In the fall, he went around raking leaves for $20 a yard, and between him and his friend, they came up with $100 in just a couple hours. Shoveling snow was just in occasional job, but since hockey and school took up most of his time in later fall through winter, it was mainly the other two jobs that gave him some money throughout the year until he joined the SMJHL.