Hale started as a young Jehu in his father’s single coach business, and at age 26 he was managing the family business. He then organized and consolidated opposing stage lines to launch the Eastern Stage Company. During the difficult times of economic hardship in Newburyport, Hale continued to provide passenger and mail service from Newburyport to Boston and Portsmouth NH. In 1814, Hale purchased a large brick building for the new Wolfe Tavern which became the headquarters of Eastern Stage. The Eastern Stage Company was successful and became an acknowledged power in the stagecoach industry for more than 20 years. In 1833, Eastern had 500 horses and 60 stages, was debt-free, and had no accidents or injuries. Hale was later awarded a Presidential appointment as the Postmaster in Newburyport, a prestigious position in town.