"You're going to Napa in your Cessna? Me too! If you let me hop in, I'll pay my share of the gas!" That arrangement is legal, but the FAA has declared that connecting brave passengers with amateur pilots for a fee is definitely a no-no. The ruling came from a request for clarification by a company called Airpooler, a small plane equivalent of UberX. That service and others like FlyteNow let private pilots post listings for flight dates and destinations, along with a corresponding fee. Thanks to a 1963 decision, such sharing is legal if done by word of mouth or a notice board, provided the pilot only asks for a fair share of the expenses. However, in a rather confusing letter, the regulator told Airpooler that its service violates the spirit of that ruling. Instead of offering a bonafide "joint venture with a common purpose," participating pilots are "holding out to transport passengers for compensation." That means unless you have a commercial ATP or CPL license, using those services is DOA.