“Uber in the sky,” while catchy, does not accurately capture the business models of Flytenow and AirPooler. Instead, pilots would post to an online bulletin board on a semiprivate website, members would decide which flight to join based on a common destination, and the pilot and each passenger-member would pay a pro rata share of the expenses. This so-called “flight-sharing” is not a new concept. In fact, the Federal Administrative Agency (FAA) explicitly wrote private pilot flight-sharing exceptions into its rules far before Uber or the Internet were even conceived. It was, and still is, permissible for a private pilot to fly others and charge a pro rata share of expenses under FAA rules. So long as the fees charged merely cover costs, the FAA has historically been permissive.
Alexander P. Cohen, Sharing the Skies: The Legal State of “Flight-Sharing” After Flytenow and Current Regulatory Issues with Lyfting the Sharing Economy Off the Ground, 82 J. Air L. & Com. 587 (2017)