Since 2013, a company called Airpooler has tried to bring the rideshare model to private aviation, providing a Web interface to connect private pilots with potential passengers who might be going their way and be willing to help defray flight costs.
In May, the company asked the Federal Aviation Administration (FAA) whether this model ran afoul of its regulations in any way. The agency answered in August that, alas, pilots using Airpooler "would be holding out to transport persons or property from place to place for compensation or hire," and that this was forbidden. The FAA's somewhat confusing letter seemed to offer some possibility for a loophole if pilot and passenger had a "common purpose" for traveling and it wasn't just about cost-sharing.
According to Airpooler co-founder Steve Lewis, the operation managed to see a 60 percent expansion in members and listings in the month after the FAA sent its letter. Still, although the authorities did not technically ban Airpooler, "the FAA's decision has made it difficult to raise growth capital."
Airpooler for now restricts pilot compensation to strict pro-rata passenger share of costs. Lewis says, "we're essentially treading water as a business whose ambition is to open up a whole new industry by bringing the share economy to general aviation."