Harry Loeb Jacobs grew up in Dayton,OH, was educated in private schools, and studied law at the University of Michigan. As a very young man he learned shorthand and traveled the United States as secretary to a senator. He became assistant principal at the Rhode Island Commercial School in Providence in 1906 and, the following year, he purchased the school. Jacobs was a natural talent in public relations. He planned graduations strategically, compelling the most notable citizens to attend.

By 1916, the Rhode Island Commercial School was so successful that Jacobs endeavored to expand and he purchased Bryant and Stratton from his aging competitor, Theodore Stowell. Jacobs moved Bryant and Stratton to the Butler Exchange Building, located in Providence's transportation hub, and merged it with the Rhode Island Commercial School.