Abstract: Trip classifying systems and methods include one or more servers communicatively coupled with a mobile device, one or more data stores, and a trip classifying device. The trip classifying device includes a housing, a processor, a wireless communication module, a speaker, a business selector, a personal selector, and a microphone. In response to a signal received from a mobile phone indicating that the trip has begun, the trip classifying device provides a notification to the driver to classify the trip. In response to receiving the user selection of the business selector, the system automatically initiates an audio recording for the driver to dictate a business purpose for the trip. The audio recording is transmitted to the mobile phone which initiates transcription and later displays the transcription on a user interface of the mobile phone. The trip classifying device may have no trip classifying selectors except the business and personal selectors.