Jesse's career as a milkman started when he was 15. The milkman who delivered to his house offered him a summer job. He got hired for $40 a day, and all the chocolate milk he could drink. His job was to run milk up to the doorstep. Soon he was driving and delivering, loving the freedom of the road and enjoying the exercise, as well as the interaction with the customers and children who look forward to having their milk delivered. He even met his wife at an espresso stand that he used to deliver to, and they have a daughter named Emma.