An information processing apparatus connected via a communication network, the information processing apparatus including a setter configured to set a communication path by adding a communication port between the information processing apparatus and another information processing apparatus to transmit first content data of a first content; and a transmitter configured to transmit, to the other information processing apparatus, second content data of a second content created with respect to the first content according to a communication system using an electronic blackboard that is a second information processing system, from the communication port added to set the communication path between the information processing apparatus and the other information processing apparatus to transmit the first content data of the first content according to an electronic conference system that is a first information processing system.