At the age of 19, Will fulfilled a childhood ambition to be a conductor on a Euclid Avenue horsedrawn streetcar. At the end of 3½ years, he left the streetcar job with saving of $1,100 and some valuable insight from the businessmen who daily rode the car. As Will said, "I carried away a miscellaneous jumble of information that just needed a little straightening out to be the basis of a good education in business."